123201285036_unit7complete2012-2013 by huangyuarong

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									              Honors Chemistry
                    Unit 7A
Organic Chemistry
  Allotropes
  Isomers
  Hydrocarbons
     o Alkanes
     o Alkenes
     o Alkynes
     o Aromatics
  Alkyl Halides




                                 1
We are learning to:

1.   Draw, model and name the hydrocarbon families
2.   Recognize isomers of hydrocarbons


We are looking for:

       1. a. Given a name, draw the structural formula for Alkanes, Cycloalkanes,
          Alkenes, Cycloalkenes, Alkynes, Cycloalkynes, aromatics.

          b. Given a structural formula, write the name for Alkanes, Cycloalkanes,
          Alkenes, Cycloalkenes, Alkynes, Cycloalkynes, aromatics.

          c. Given a model, write the name for Alkanes, Cycloalkanes, Alkenes,
          Cycloalkenes, Alkynes, Cycloalkynes, aromatics.

       2. Draw and name isomers of given hydrocarbon




                                                                                 2
3
4
5
      Parent Chain:

      Methane            CH4

      Ethane             C 2 H6

      Propane            C 3 H8

      Butane             C4H10

      Pentane            C5H12

      Hexane             C6H14

      Heptane            C7H16

      Octane             C8H18

      Nonane             C9H20

      Decane             C10H22

      Undecane           C11H24

      Dodecane           C12H26

Branches (one less Hydrogen than Parent Chain):
all prefixes can be made into branches


      Methyl             CH3

      Ethyl              C 2 H5


                                                  6
Introduction of parent chain and branches




                                            7
                     Organic Chemistry
   Hydrocarbons contain Carbon and Hydrogen only
   If all bonds on the carbons are single bondsdrocarbon
Alkanes
     Have form CnH2n+2 (where n = # of carbons)
     Ending of the name is “ane”

  Name              Molecular   Structural Formula   Model
                    Formula


                    CnH2n+2
  Methane



  Ethane



  Propane



  Butane



  2-Methylpropane




Example 1:

                                                             8
3-ethylheptane



Example 2:


2,7-dimethylnonane



Example 3:


4-ethyl-2,4,5-trimethyloctane




Example 4:


3,3,4,4-tetraethyl-2,2,5,5-tetramethylhexane




Cycloalkanes
     All single bonds
     Have form CnH2n
     Ends of chain bond together (lose 2 hydrogens)

Examples:




                                                       9
More practice -

Naming Alkanes




Drawing Alkanes




                  10
Unsaturated Hydrocarbons                = not all carbons have 4 single bonds
(double or triple bonds)


Alkenes
     Structure contains double bonds
     Have form CnH2n

      Name           Molecular     Structural Formula       Model
                     Formula


                           CnH2n
      Ethene



      Propene



      2-Butene




Drawing and naming Alkene structures:




                                                                           11
More drawing and naming alkenes




                                  12
Alkynes
     Structure contains triple bonds
  


Have form CnH2n-2
      Name            Molecular Formula   Structural Formula


                              CnH2n-2
      Ethyne



      1-Propyne



      1-Butyne




Naming and drawing Alkynes:




                                                               13
     Aromatic Hydrocarbons
   Mu
st contain at least one benzene ring




  Naming Aromatics




                                       14
Date__________                                    Name ____________________________________ Class ______

                                          Modern Chemistry Lab Practical

                                             Unit on "Organic Chemistry"

I. Problem: What are some of the differences between various organic compounds? You will be given some notes and
       then asked to design a model of these organic compounds including: alkanes, isomers of alkanes, alkenes,
       alkynes, alcohols, organic acids, aldehydes, ketones and some nitrogen containing organic compounds.
II. Background Information: Alkanes are saturated hydrocarbons with a formula of CnH2n+2. Isomers of alkanes
        would have the same formula but different structures. Other information will be given at the beginning of each
        day of this lab practical.

III. Hypothesis:

IV. Test The Hypothesis:
Materials: make certain your kit contains the following in the right location. If it does not, the previous user will be
               marked at least 1 point off their next assignment grade each day there is a problem. Each day you work
               with the kit, you are to sign the paper in the kit with your class numbers and date.

                10 black spheres -       carbon     \ place these on the small side of your kit
                2 blue spheres -         nitrogen /
                28 yellow spheres -      hydrogen \
                6 red spheres -          oxygen       \
                4 green spheres -        chlorine       \ place these on the larger side
                2 orange spheres -       bromine        / of your kit
                2 white spheres-         fluorine /        (all colors are to be placed together)
                2 purple spheres-        iodine     /

                30 small wooden pegs - H bonds only               \
                10 large wooden pegs - other single bonds           \ place these in the
                9 metal springs -               double or triple bonds       / center of your kit
                                                or stress bonds /




V. Observations: The first student lab team that has the structure correct will be initialed by the instructor and receive a
              grade of 2 points out of 1 point. These students will then have their names placed on the board and will
              be teaching assistants for that organic structure. They will be responsible to grade and initial the
              structures of other lab teams. Each structure that is designed and named by you is worth 1 point. The
              following is the grading criteria:
                      2 points          = graded by the instructor and perfect, this team assists in grading
                      1 point           = other perfect scores
                      0 points          = 1 or more mistakes in the structure and/or name




                                                                                                                     15
Assignment # ____                   Name ____________________________________                   Class Number ______

Date ________                       Name ____________________________________                   Class Number ______

Kit # _______
                                             Honors Chemistry Lab Practical
                                                    "Organic Chemistry"

                                              Alkanes – Straight and Branched


(If absent - write an I-search paper describing the major uses of each of the first 10 alkanes. This must be written in the first
         person. Answer the 3 questions on page 17 using the criteria of an I-Search.)

(2 points, ½ point each)


Grade/Initials

_______________ 1.         hexane




_______________ 2.         3-methylpentane




_______________ 3.         2, 4-dimethylhexane




_______________ 4.         2, 2-dimethylpentane




_______________ 1 point lost for problems with your kit



           /2
_______________Total points for Straight and Branched Alkanes




                                                                                                                           16
Information on Doing an “I-Search” Paper to Make-Up a Missed Organic Chem Modeling Lab:




         1. An "I-Search” paper is telling the story of what you did in your search, those happenings and
            facts crucial to your hunt for information on your assigned topic.
            You are to write 150 words (one page) for each modeling lab you miss.


         2. The paper is to be typed and divided into three parts (each section is to be titled as below):
                       a. What I knew before I started my search.
                       b. The facts I found in my search and what I learned.
                       c. What I found the most interesting with what I learned.


         3. If your make-up paper does not answer these questions, the best score you can receive
            is half credit.




                                                                                                     17
   Name ______________________________________________


                                          Alkane Worksheet

Based on the given IUPAC name, give the structural formula for each of the following
molecules (number the carbons):


                        Name                                 Structural Formula
     1.

     dodecane



     2.

     2-methylheptane



     3.

     2,3,4-trimethylhexane



     4.

     3-methylpentane



     5.

     3-ethyl-2,4,4-trimethylnonane



     6.

     1-butyl,2,4-diethyl-3-methyl cyclobutane




                                                                                       18
Give the IUPAC name for each of the following molecules (number the carbons):

                 Name                          Structural Formula
    1.

                                      CH3-CH2-CH2-CH2-CH2-CH2-CH3



    2.
                                                  CH3
                                                  
                                              CH3-CH-CH2-CH3

    3.
                                            CH3    CH3 CH3
                                                   
                                        CH3-CH-CH2-CH-CH-CH3

    4.                                                   CH2-CH3
                                                     


                                                          CH3


    5.                                        CH3           CH3
                                                            
                                              CH2           CH2
                                                            
                                      CH3-CH2-CH-CH2-CH2-CH-CH2-CH3
    6.                                    CH3     CH3       CH3
                                                          
                                          CH2 CH2           CH2
                                                          
                                      CH3-CH-CH-CH2-CH2-CH-CH2-CH3


                                                                            19
Introduce Isomers




                    20
Assignment # ____          Name ____________________________________                Class Number ________

Date ________              Name ____________________________________                Class Number ________

Kit # _______
                                           Honors Chemistry Lab Practical
                                                "Organic Chemistry"


                                                         Isomerism


(If absent - write an I-search paper on organic isomers. This must be written in the first person. Answer the 3 questions on
         page 17 concerning an I-Search.)

(2 points, ½ point each)

Grade/Initials: Do not use –iso or –neo. Use the naming system found in 19.4.


_______________ 1. butane isomer #1                        name _____________________________________
             (simple)               (0.25 point)                               (0.25 point)


_______________ 2. butane isomer #2                        name _____________________________________
              (one branch) (0.25 point)                                        (0.25 point)


_______________ 3. pentane isomer #2                       name _____________________________________
             (one branch) (0.25 point)                                         (0.25 point)


_______________ 4. pentane isomer #3                       name _____________________________________
       (two branches) (0.25 point)                                             (0.25 point)




_______________ 1 point lost for problems with your kit




           / 2
_______________ Total points for Isomerism



                                                                                                                       21
Name _____________________________________________

                   Draw and NAME the 18 isomers of Octane

Octane:
   1.


Methyl heptane:
   1.


   2.


   3.


Dimethyl hexane:
   1.


   2.


   3.


   4.


   5.


   6.

                                                            22
Ethyl hexane:
    1.

Trimethyl pentane:
    1.




    2.




    3.




    4.




Ethyl methyl pentane:
    1.




    2.




Tetramethyl butane:
    1.


                        23
Assignment # ____          Name ____________________________________               Class Number ________

Date ________              Name ____________________________________               Class Number ________

Kit # _______
                                             Honors Chemistry Lab Practical
                                                  "Organic Chemistry"

                                                Unsaturated Hydrocarbons

(If absent - write an I-search paper unsaturated hydrocarbons. This must be written in the first person. Answer the 3
         questions on page 17 of your packet.)

(3 points, ½ point each)

Grade/Initials

_______________ 1.         1-butene


_______________ 2.         2-butyne


_______________ 3.         2-methylpropene


_______________ 4.         3-methylbutene


_______________ 5.         1, 3-pentadiene


_______________ 6.         4-methylpentyne




_______________ 1 point lost for problems



       / 3
_____________ Total points for Unsaturated Hydrocarbons




                                                                                                                        24
Name ______________________________________________

                                     Alkene Alkyne Assignment

Based on the given IUPAC name, give the structural formula for each of the following
molecules (number the carbons):

                   Name                               Structural Formula
1.
3-heptene



2.
3-methyl-butyne



3.
4,5,5-trimethyl-1-hexene



4.
3-ethyl-2,4-dimethyl-2-pentene



5.
5-methyl-1,3-hexadiyne



6.
1,2,4-trimethyl-1-cyclopentene



7.
2,4,5-trimethyl-1,3-cyclohexadiene




                                                                                       25
Give the IUPAC name for each of the following molecules (number the carbons):
                 Name                             Structural Formula
   1.
                                         C–C–C=C-C-C

   2.                                            C
                                                 
                                           C=C–C–C-C

   3.                                        C     C
                                                  
                                           C-C-C - C-C=C

   4.                                            C          C–C-C




   5.                                          C     C
                                                     
                                               C      C
                                                     
                                        C -C = C–C=C-C–C
   6.                                            C C
                                                  
                                              C C C
                                                
                                        CΞC-C - C-C -C≡C
   7.

                                             C                C -C




                                                                                26
       Alkyl Halides:

             Organic compound with



             General Formula



                     o   –
                     o   –
                     o   –
                     o   –

             Naming:

                     o   Name as if the halogen is a branch

Examples:




                                                              27
Assignment # ____          Name ____________________________________               Class Number ________

Date ________              Name ____________________________________               Class Number ________

Kit # _______
                                             Honors Chemistry Lab Practical
                                                    "Organic Chemistry"

                            Mixed Aromatic Hydrocarbons, Alkyl Halides and Hydrocarbons

(If absent - write an I-search paper unsaturated hydrocarbons. This must be written in the first person and be 150 words.
         Answer the 3 questions on page 16 of your packet concerning an I-Search.)

(3 points, ½ point each)

Grade/Initials

_______________ 1.         2-chloropropane


_______________ 2.         2-bromo-3,4 -dichloropentene


_______________ 3.         5-bromo-1- chloro-4,4-diiodo-5-methyl-2- hexyne


_______________ 4.         ethylbenzene


_______________ 5.         1-ethyl-3-methylbenzene


_______________ 6.         1,2,4-trimethylbenzene




_______________ 1 point lost for problems with your kit




       / 3
_____________ Total points for Aromatics and Alkyl Halides



                                                                                                                      28
                 Alkane, Alkene, Alkyne, Cyclos and Aromatic Review Sheet



Section 1: Draw the following structures:

         1. 1-ethyl-2-methyl-cyclohexane




         2. 2,3-dimethyl-1,5-heptadiene




         3. 3-bromo-4,5-dichloro-6-iodo-undecane




         4. 1-butyl-3-propyl-benzene




         5. 3.3.4-trifluoro-1,6-octadiyne




         6. 1-ethyl-4-methyl-1,3-cycloctadiene




         7. 1-bromo-5,6-dichloro-3-fluoro-2,4-dimethyl-benzene


                                                                            29
30
Assignment # ____   Name ____________________________________ Class Number ________

Date ________              Name ____________________________________ Class Number ________

Kit # _______
                                 Honors Chemistry Lab Practical
                                       "Organic Chemistry"

                                        Mixed Hydrocarbons



_______________ 1. 2, 3, 4-trimethylhexane


_______________ 2. propylcyclobutane


_______________ 3. Methylbenzene


_______________ 4. 1,1-difluoro-2-butyne


_______________ 5. 1-iodo-2-methylpropene


_______________ 6. 1, 3-pentadiene


_______________ 7. 3-bromo-1-chlorobutyne


_______________ 8. 1-chloro-2-ethyl-3fluoro-cyclohexene



          / 8
_______________ Total points for Mixed Hydrocarbons




                                                                                       31
32
               Honors Chemistry
                      Unit 7B
Organic Chemistry continued
  Alcohols
  Ethers
  Aldehydes
  Ketones
  Carboxylic acids
  Esters
  Amines




                                  33
We are learning to:

  1. Draw, model and name the hydrocarbon families.
  2. Recognize isomers of hydrocarbons.
  3. Draw, model and name the functional groups



We are looking for:

1 & 3 a. Given a name, draw the structural formula for Alkanes, Cycloalkanes,
      Alkenes, Cycloalkenes, Alkynes, Cycloalkynes, aromatics, alkyl halides,
      alcohol, ether, aldehydes, ketones, carboxylic acids, esters, and amines.

     b. Given a structural formula, write the name for Alkanes, Cycloalkanes,
     Alkenes, Cycloalkenes, Alkynes, Cycloalkynes, aromatics, alkyl halides, alcohol,
     ether, aldehydes, ketones, carboxylic acids, esters, and amines.

     c. Given a model, write the name for Alkanes, Cycloalkanes, Alkenes,
     Cycloalkenes, Alkynes, Cycloalkynes, aromatics, alkyl halides, alcohol, ether,
     aldehydes, ketones, carboxylic acids, esters, and amines.

2. Draw and name isomers of given hydrocarbon




                                                                                  34
Information on Doing an “I-Search” Paper to Make-Up a Missed Organic Chem Modeling Lab:




         1. An "I-Search” paper is telling the story of what you did in your search, those happenings and
            facts crucial to your hunt for information on your assigned topic.
            You are to write 150 words (one page) for each modeling lab you miss.


         2. The paper is to be typed and divided into three parts (each section is to be titled as below):
                       a. What I knew before I started my search.
                       b. The facts I found in my search and what I learned.
                       c. What I found the most interesting with what I learned.


         3. If your make-up paper does not answer these questions, the best score you can receive
            is half credit.




                                                                                                     35
                                   Other Organic Compounds

   Functional Group –



   Same Functional Group

        o   -
        o   -


Alcohols:

   Organic compound that



   General Formula

   Naming:

        o   If no number is present in front of the name – presume the –OH is on carbon number 1.

        o   If 1 -OH group
                  -

     Examples:




        o   If two or more -OH groups
                  2=
                  3=
                  4=

         Keep the ane; add the appropriate ending listed above:




     Examples:


                                                                                                    36
Classification of Alcohols:



For classification –



If that carbon is attached to one other carbon, it is called a   ______________


                              C - C - C - OH


If that carbon is attached to two other carbons, the compound is called a ________________________



                                      OH
                                      
                                   C-C-C-C




If that carbon is attached to three carbons, it is called a ____________________




                               OH
                                
                             C-C-C–C
                               
                               C




                                                                                                     37
Ethers:


      Organic compounds




      General Formula:




   - R and R’




    Naming:


            o–
            o–
            o–


Examples:




                           38
Assignment # ____                  Name ____________________________________                      Class Number ________

Date ________                      Name ____________________________________                      Class Number ________

Kit # _______
                                              Honors Chemistry Lab Practical
                                                     "Organic Chemistry"

                                                       Alcohols and Ethers

(If absent:- Write an I-search paper describing an alcohol or ether and how it is used in everyday life. This must be written in
         the first person. See page 35 of the packet for questions to answer.)
(5 points)
Grade/Initials

_______________ 1. 2-methylpropanol


_______________ 2. 2-propanol (rubbing alcohol)


_______________ 3. 1,2,3-propanetriol


______________ 4. Butyl ethyl ether


_______________ 5.       Dicyclopentyl ether




_______________ 1 point lost for pieces missing from your kit, above not filled-in completely or not totaled on the line above.
                       (Your total will change if the above is not done)



          / 5
_______________ Total points for Alcohols and Ethers




                                                                                                                             39
Name__________________________________________




                                    Other Organic Compounds – WS I

Draw the following compounds (number the parent chain and circle any branches):

1. 1,8 nonanediol                       2. 1, 3, 5 trimethylbenzene                3. 2-bromo-2-fluoro propane




4. dibutyl ether                5. 4-decanol                                       6. 1-iodocyclobutane




7. 1,2dibromo -1-chloroethane          8. 4-ethyl -3,6-difluoro-5-propyl-1-cyclohexene




9. 2,3-dichloro-7,8,9-triiodo-6,7,8-tripropyl-4-dodecene




10. 1,2,3,4,5,6-hexafluoro-1-hexanol                       11. Decyl octyl ether




                                                                                                                 40
         Othe
           r
          Org
          anic
           Co
           mp
           ou
           nd
             s
             C
             o
             n




tinued

         41
Carbonyl group is C=O



Aldehydes:

   Organic compounds




                               O
                               
   General Form:            R–C–H




   Naming:

                -




Example

                       O
                           ethanal
                     C-C-H




Ketones:

                                       42
   Organic compound


                              O
                            
   General Form:        R – C – R’




   Naming:




Example:                  O           2-propanone
                         
                       C–C-C




Carboxylic Acids:
                                         O
                                                    43
Carboxyl group is                                   
                                                  - C – OH



Organic compounds

                                    O
                                   
 General Form:                 R – C - OH


 Naming:


      o If one carboxyl group


                -

      o If more than one carboxyl group



                -

                      For 2 = dioic acid



Example:                    O        O
                                  
                      OH – C – C – C – C – OH
                                                             1,4-butanedioic acid


Assignment # ____          Name ____________________________________   Class Number ________

Date ________              Name ____________________________________   Class Number ________

                                                                                           44
Kit # _______
                                             Honors Chemistry Lab Practical
                                                     "Organic Chemistry"

                                                     Aldehydes and Ketones


(If absent:- Write an I-search paper describing an aldehyde or ketone and how it is used in everyday life. This must be written
         in the first person. See page 35 for details of an I-search.)
(5 points)


Grade/Initials

_______________ 1. propanone (acetone)


_______________ 2. 2-methylpropanal


_______________ 3. 2,2-dimethylpentanal


_______________ 4. methanal (formaldehyde)


_______________ 5. 2-pentanone




       / 5
_______________ Total points for Aldehydes and Ketones

______________ 1 point lost for pieces missing from your kit, above not filled-in completely or not totaled on the line above. (Your
                        total will change if the above is not done)




                                                                                                                             45
Assignment # ____                  Name ____________________________________                      Class Number ________

Date ________                      Name ____________________________________                      Class Number ________

Kit # _______
                                              Honors Chemistry Lab Practical
                                                     "Organic Chemistry"

                                                         Carboxylic Acids


(If absent:- Write an I-search paper describing a carboxylic acid and how it is used in everyday life. This must be written in
         the first person. See page 35 for details of an I-search.)
(5 points)


Grade/Initials

_______________ 1. butanoic acid


_______________ 2. 3-methylpentanoic acid


_______________ 3. 3, 3-difloro-4-ethylhexanoic acid


_______________ 4. 2-butylpropanedioic acid


_______________ 5. 4-ethyl-2-methylheptanoic acid




         / 5
_______________ Total points for Carboxylic Acids


_______________ 1 point lost for pieces missing from your kit, above not filled-in completely or not totaled on the line above.
                       (Your total will change if the above is not done)




                                                                                                                             46
Name__________________________________________


                                    Other Organic Compounds – WS II

Draw the following compounds (number the parent chain and circle any branches):

1. 1,5 pentanedioic acid        2. 1 heptanal                           3. 3-hexanone




4. 1,2,4 tributyl benzene               5. 3,5 dimethyl- 4 propyl octane                6. Butyl methyl ether




7. 1,2-dichlorocyclohexane                      8. Dicyclopentylmethanone




9. 3-iodo-1-propanal         10. 4,5,6,7-tetrabromo -3,8 dichloro -5,6-diethyl-3,8-dimethyl-1,10-decanedioic acid




                                                                                                                    47
48
                               More Organic Compounds
                                  Continued (again)!

Esters:

Organic compounds




     O              O
                 
 R - C - OH    R - C - O - R’
  (Acid)                 (Ester)



Naming:
      Parent Chain
          o
          o
          o
          o
      Branches
          o
          o

Example:

         O
        
     C - C - O - C - C-C
     2 1         1 2 3
      (Parent)     (Alkyl branch)



                                                        49
Parent Chain:



Branch:



Final Name:

Example:



            O
           
C - C - C - C - O - C - C
4 3 2 1             1 2



Parent Name:



Branch:



Final Name: ____________________



Draw: Pentyl Hexanoate




                                   50
Amines:

Organic compounds based on NH3
                                         R - N - R”
                                             
                                             R’
Naming:

   
   

Primary amine:
(______ hydrogen is replaced by an alkyl group)              C–N–H
                                                               
                                                               H

Name: ___________________________

Secondary amine:
(____ hydrogens are replaced by alkyl groups)         C–N–C - C
                                                        
                                                        H

Name: _____ ______ _______________

Tertiary amine:
(____ hydrogens are replaced by alkyl groups)           C–N–C - C
                                                          
                                                          C–C-C




                                                                     51
Assignment # ____                  Name ____________________________________                      Class Number ________

Date ________                      Name ____________________________________                      Class Number ________

Kit # _______
                                              Honors Chemistry Lab Practical
                                                     "Organic Chemistry"

                                                        Esters and Amines


(If absent:- Write an I-search paper describing an ester or amine and how it is used in everyday life. This must be written in
         the first person. See page 16 for details of an I-search.)
(5 points)


Grade/Initials

_______________ 1. butylamine


_______________ 2. ethylpropylamine


_______________ 3. ethylmethanoate (an ester)




Design one of the following for 2 points, if right it is placed on the board and other teams may not use it:


_______________ 4. design an ester                            name _____________________________________
                     with 5 carbons total                            (can not be straight chain)(Instructor checks)


_______________ 5. design an ester                            name _____________________________________
                     with 7 carbons total                            (can not be straight chain)(Instructor checks)




     / 5
_______________ Total points for Esters/Amines

_______________ 1 point lost for pieces missing from your kit, above not filled-in completely or not totaled on the line above.
                       (Your total will change if the above is not done)
                                                                                                                             52
Name: __________________________________________________



                                             Ester and Amine Worksheet

Draw each of the following compounds:



1. ethyl butanoate                      2. propyl-benzoate                      3. propylamine




4. diethylamine              5. butylethylpropylamine                    6. hexyloctylamine




7. methyl-2-methylhexanoate 8. propyl pentanoate                9. phenyl butanoate




                                                                                                 53
54
                             Organic Compounds




Family          Functional Group      Ending     Naming



Alkane




Alkene




Alkyne




Aromatic




Alkyl halides




Alcohol




                                                          55
Family            Functional Group   Ending   Naming



Ether




Aldehyde




Ketone




Carboxylic Acid




Ester




Amine




                                                       56
Assignment # ____             Name ____________________________________   Class Number ________

Date ________                 Name ____________________________________   Class Number ________


Kit # _______
                                        Honors Chemistry Lab Practical
                                              "Organic Chemistry"

                                                     ALL Mixed Up

Grade/Initials

_______________ 1. 4-methyl-2,3-octanediol


_______________ 2. 3-chloro-3-ethyl-2,2,4-trimethylpentane


_______________ 3. 3-propylhexanoic acid


______________ 4. Butyl methyl propyl amine


_______________ 5.    Pentyl propyl ether


_______________ 6.    1-bromo-4-iodo-2-propylbenzene


_______________ 7.    6,6-difluoro-3-methyl-3-propyl-1,4-hexadiyne


_______________ 8.    3-methyl-2,2-difluorobutanal


_______________ 9.    4-ethyl-6-iodo-3,3-dimethyl-1-cyclohexene


_______________ 10.    Propylbenzoate


_______________ 11.    5-fluoro-2-methyl-3-hexanone


_______________ 12.    1-fluoro-2-methyl-3-hexanone


Total Points =        / 6
                                                                                              57
58
Name: __________________________________________________



                                          Mixed Worksheet

Draw each of the following structures:



1. 1-chloro-2-pentyl-4-propyl benzene        2. 5-fluoro-2-octyne




 3. 2-iodo-3-methyl butanedial               4. 5,5-dibromo-1,1,1-trifluoro-8-ethyldecane




5. propyl undecyl ether                        6. 1,3,6-heptatriene




7. 2,5-dimethyl-1-cyclopentanone             8. 2,3,4,5,6-pentafluoro-1-nonanal




  9. 1,4,9,11-dodecanetetrol                 10. 4-bromo-5-butyl-3-ethyl-1-cycloheptyne




                                                                                            59
60
Name ___________________________________________________________



                                       Review for Organic Quest



Part 1: Draw and name each of the six models:



         #1                                      #2




         Name                                    Name

         #3                                      #4




         Name                                    Name

         #5                                      #6




         Name                                    Name




                                                                   61
Part 2: Draw the following structures:



   1. 1,4,7-octanetriol
   2. 2,4-dibromo-3-fluoro-1-hexene
   3. heptyl hexyl ether
   4. butyl pentanoate
   5. 3-chloro-5-ethyl heptanal
   6. dodecane
   7. 4-bromo-5,5-difluoro-3-decanone
   8. butyl ethyl pentyl amine
   9. 2,3-dimethyl 4-nonene
   10. 1-bromo-4-butyl-2-ethyl-3 propyl benzene
   11. 1,4,5,trichloro-2-pentyne
   12. 2,3,5,7,9 pentabromo-1,4,8-trichloro-6,6 diiodo undecane




                                                                  62
63
64
                                              Polymers
The word comes from the Greek polumeres, which means `having many
parts. Polymers are large molecules consisting of repeated chemical
units (‘monomers') joined together, usually in a line, like beads on a
string. Each `mer' is typically made up of more than 5 and less than
500 atoms; the word `polymer' is applied when you have more than
about 50 `mers' stuck together. Your body is made of polymers. Amino
acids (proteins) and nucleic acids (RNA and DNA), the genetic blueprint
that defines people and other living things, are polymers, as well as
cellulose and starches in the foods we eat. The most powerful
computers - our brains - are mostly just a polymer glob soaking in salty
water! The wheels on our skateboards and in-line skates, tires on our
bikes and cars, various plastic containers, and clothing are just a few
other examples. In fact, polymers surround us every day everywhere
we go.




Two important polymeric materials are plastics and elastomers. Plastics are a large and varied group of
synthetic materials, which are processed by forming or molding into shape. We have many types of plastics
such as polyethylene and nylon. Plastics can be divided into two classes, thermoplastics and thermosetting
plastics, depending on how they are structurally and chemically bonded. Elastomers or rubbers can be
deformed when a force is applied to them and can return to their original shape (or almost) when the force
is released.




Some Naturally Occurring Polymers
Lac
The insect Laccifer lacca—or just plain “lac”—lives on trees in India and Southeast Asia. It secretes a resin,
also called lac, a polymer from which people make lacquer and shellac. They use these varnishes to coat
ships, houses, furniture, fruit, pills, and candy.




Rosin
Dead wood and pulp from pine trees contain a polymer called rosin, which is used to make varnish and soap.
Violinists rub rosin on the horsehairs in their bows to make them slide smoothly across the strings.
Gymnasts and baseball players use rosin to improve their grips.

                                                                                                       65
Latex
South American Indians slash the bark of trees in the
rain forest to obtain a milky white fluid called latex. They
discovered that it could form a solid that was elastic; you
could stretch it and it would snap back to its original
shape. If you rubbed it on penciled words, the writing
would disappear, so Europeans called it rubber. They           In 1839 Charles Goodyear discovered
molded it into tires for carriages and automobiles.            that latex heated with sulfur—or
                                                               “vulcanized”—would remain elastic at a
Milk                                                           wide range of temperatures. Although
Drink up! Cow’s milk is loaded with the polymer casein, a      Goodyear didn’t know why his invention
                                                               worked, we do today: The sulfur made
protein. Without this polymer, cheese would come unglued.
                                                               bridges between the long chain polymers
Glue would come unglued too, since casein from milk
                                                               in rubber to keep them from sliding past
provides its sticking power. Casein also winds up in
                                                               one another or contracting into knots.
buttons, as well as rhinestones and other artificial
gemstones.


Amber
Fossilized tree sap made of resin polymers can become yellow, orange, or brown amber.
Ancient Greeks called amber “elektron,” and its ability to give a static electrical shock
gave electrons and electricity their names. Scientists have retrieved intact genetic
polymers, DNA, from ancient insects trapped in amber. Some even think the tiny
bubbles in amber might hold the last remaining samples of air breathed by dinosaurs
more than 60 million years ago.


Silkworm
Silkworms, which are actually caterpillars, are raised on silk farms and fed mulberry leaves.
People in China discovered more than 4,500 years ago that they could unravel silk, a polymer,
from the worms’ cocoons and weave it into soft fabrics. Incredibly, a single cocoon yields
330 to 980 yards (300 to 900 meters) of silk. For centuries, silk was so prized that
exporting mulberry seeds or silkworm eggs from China was punished by death.

Styrofoam
Polystyrene foam can be made into cartons to protect eggs or into packing “peanuts” to cushion
fragile objects for shipping. It insulates, so folks put drinks in foam cups and coolers to keep the
warm ones warm and the cold ones cold.




                                                                                                       66
                                        Types Of Polymers
Polymers are formed by chemical reactions in which a large number of molecules called monomers
are joined sequentially, forming a chain. In many polymers, only one monomer is used. In others,
two or three different monomers may be combined. Polymers are classified by the characteristics
of the reactions by which they are formed. If all atoms in the monomers are incorporated into the
polymer, the polymer is called an addition polymer. If some of the atoms of the monomers are
released into small molecules, such as water, the polymer is called a condensation polymer.


                                              Copolymers
The synthesis of macromolecules composed of more than one monomeric repeating unit has been explored
as a means of controlling the properties of the resulting material. In this respect, it is useful
to distinguish several ways in which different monomeric units might be incorporated in a polymeric
molecule. The following examples refer to a two component system, in which one monomer is designated A
and the other B.


Statistical Copolymers       Also called random copolymers. Here the monomeric units are distributed randomly,
                             and sometimes unevenly, in the polymer chain: ~ABBAAABAABBBABAABA~.

Alternating Copolymers       Here the monomeric units are distributed in a regular periodic fashion, with nearly
                             equimolar amounts of each in the chain: ~ABABABABABABABAB~.

Block Copolymers             Instead of a mixed distribution of monomeric units, a long sequence or block of one
                             monomer is joined to a block of the second monomer:
                             ~AAAAA-BBBBBBB~AAAAAAA~BBB~.

Graft Copolymers             As the name suggests, side chains of a given monomer are attached to the main
                             chain of the second monomer: ~AAAAAAA(BBBBBBB~)AAAAAAA(BBBB~)AAA~.

Polymer Properties
       While they all contain molecules with very long chains, there are some important differences
between the properties of different types of polymers. Most polymers are formed into the desired shapes
after softening or melting by heating. Some, like the familiar polyethylene and polystyrene, may be melted
and reshaped again and again. These are called thermoplastic polymers. Many of these polymers are
recycled.

Thermosetting polymers char or burn when reheated. Examples include Bakelite and vulcanized rubber. Due
to the fact that these polymers can not be reheated, it makes it much more difficult to recycle them.

The major problem with recycling plastics is that they must be sorted by polymer composition. If the
     polymers were just mixed, called commingled plastic, they would not be able to be shaped into
     useable objects. The reason for this is the physical properties such as the melting point would be
     too variable in commingled plastic.


Plastic Recycling
Over the past few decades, the use of polymers in disposable consumer goods has grown tremendously. This
growth is proving to be taxing on the waste disposal system, consuming a large fraction of available landfill

                                                                                                            67
space. Furthermore, the raw materials for these polymers are obtained from petroleum, a limited, non-
renewable resource. To reduce the demand for landfill space and the consumption of limited petroleum
reserves, the recycling of polymers has become a subject of concern. One of the problems faced in
recycling polymers is the great variety of polymers in use. To help sort wastes by type of polymer, most
disposable polymeric goods are labeled with a recycling code: three arrows around a number above the
polymer's acronym. These are intended to help consumers separate the waste polymers according to type
before disposing of them.



                                                                              Do NOT Recycle This Plastic
                                                                              1. Automotive Product
    Plastic Code Number                Plastic Code Number                    Containers Including:
                                       Recyclable Containers                  Motor Oil Bottles
                                                                              Anti-Freeze Containers
    Recyclable Containers              Milk Bottles                           Gasoline and Oil Additive
                                       Water Bottles                          Bottles
    Soda Bottles
                                       Juice Bottles                          2. Brown Liquor Bottles
    Water Bottles
                                       Cooking Oil Containers                 3. All Containers Marked With
    Juice Bottles
                                       Washer Fluid Bottles                   The Following Codes:
    Cooking Oil Bottles
                                       Shampoo Bottles
    Soap/Detergent Bottles
                                       Butter/Margarine Tubs
    Shampoo Bottles
                                       Cottage Cheese Containers
    Clear Liquor Bottles
                                       Ice Cream Containers
    Food Jars (Peanut Butter etc.)
                                       Baby Wipe Containers
What can be Recycled?

Degradable Polymers
Degradation of polymers can be accomplished by                    Code         Polymer
microorganisms or by photodegradation. Many polymers are          1 PETE       polyethylene terphthalate
made to degrade more readily by the addition of additives.        2 HDPE       high density polyethylene
Thermosetting polymers are an important target for these
                                                                  3 V (PVC)    polyvinyl chloride
additives because they cannot be recycled. Photodegradable
plastics can have an additive that is sensitive to ultraviolet    4 LDPE       low density polyethylene
light. Biodegradable plastics can have starch or cellulose        5 PP         polypropylene
incorporated into the resin at the time of manufacture.           6 PS         polystyrene
Microorganisms would consume the starch or cellulose and          7 OTHER all other
the plastic would be broken down into small pieces.
Photodegradation depends on light and oxygen, both of which are excluded in landfills. Biodegradation
depends on moisture and that also is limited in landfills. Newspapers have been found in landfills relatively
unchanged after 20 years.

.



                                                                                                          68
                                     POLYMERS




Down
1. This is another name
   for Styrofoam.
2. A milky white polymer
   from rubber trees.
3. This refers to the break down of                                        Across
   polymer with light and oxygen.                 4. Common name of HDPE and LDPE that has the monomer
4. These are a large and varied group             CH2=CH2.
   of synthetic materials, which are processed    5. Polymers that make up living organisms such as amino
   by forming or molding into shape.              acids, nucleic acids, and starch.
6. This polymer make up Spandex.                  8. ~AAAAA-BBBBBBB~AAAAAAA~BBB~ is an example of
7. If all atoms in the monomers are               this type of copolymer.
   incorporated into the polymer, the polymer     10. These are the “units” that are chained together to
   is called a(n) ________ polymer.               form polymers.(plural)
9. Milk contains this biopolymer.                 14. This category of polymers cannot be recycled because
11. In this type of copolymer the monomeric       they just decompose if they are heated.
    units are distributed in a regular periodic   16. Trees secrete this resin which is used to make lacquer
    fashion.                                      and shellac.
12. This is the abbreviation for the polymer      17. This polymer can form Fossilized tree sap.
    designated by Plastic Code Number 1.          18. This category of polymers may be melted and reshaped
13. Latex heated with sulfur to make bridges      again and again.
    between the long chain polymers in rubber.    19. This organism eats mulberry leaves and produces a
15. This class of polymers can be elastically     polymer.
    deformed a large amount when a force is       20. If some of the atoms of the monomers are released
    applied to them and can return to their       into small molecules, such as water, the polymer is called
    original shape when the force is released.    a(n) ________ polymer.
22. This type of copolymer is also called a       21. Dead wood and pulp from pine trees contain this69
   random copolymer.                              polymer that can be used to improve grip.
70
Name: __________________________________________




                                                Polymer Activity
We are going to investigate two types of polymers in this activity. There are many types of polymers – all with unique
properties.


Flubber
Materials:

        White glue                      eyedropper/pipette               stirrer

        Paper cup                       sodium borate solution



Procedure:

        1. Place about 5mL of white glue in a small cup/beaker. (this would be about a half of an inch of glue in the
           bottom of the cup)
        2. Add about 1mL of sodium borate solution one drop at a time as you stir the glue.
        3. Remove the sticky mass from the cup, rinse it with water, and roll it into a ball.
        4. Test if the ball will bounce on the table.
        5. Allow the ball to set on the table for 5-10 minutes.
        6. Pull quickly at opposite ends of the material.
        7. Pull slowly at opposite ends of the material.




List 5 properties of this polymer:

                a.

                b.

                c.

                d.

                e.




                                                                                                                     71
Guar Gum Polymer “Slime”

1.   Add 100 ml of distilled water to a plastic cup
2.   Add 1 drop of food coloring and stir
3.   Slowly and with constant stirring, add .75 grams of guar gum.
4.   YOU DO NOT WANT LARGE CLUMPS TO FORM
5.   Stir for 2 minutes – the solution will thicken slightly
6.   Add 5 ml of .1M sodium borate solution.
7.   Stir until the polymer gels.

8. List 5 properties of this polymer:

                 a.

                 b.

                 c.

                 d.

                 e.




                                                                     72
Name ___________________________________________________________

                                       Model Review



Draw and name each of the models:




                                                                   73
#1     #2
#7     #8




Name   Name
Name   Name
#3     #4

#9     #10




Name   Name
Name   Name
#5     #6

#11    #12




Name   Name


Name   Name




              74
Name ___________________________________________________________

                                       Model Review



Draw and name each of the models:



          #1                                  #2




          Name                                Name

          #3                                  #4




          Name                                Name

          #5                                  #6




                                                                   75
Name   Name




#7     #8




Name   Name

#9     #10




Name   Name

#11    #12




              76
Name   Name




              77

								
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