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					Chemistry, 11e (Brown/LeMay/Bursten/Murphy)
The Chemistry of Life: Organic and Biological Chemistry


25.1 Multiple-Choice and Bimodal Questions

1) Hydrocarbons containing only single bonds between the carbon atoms are called
__________.

A) alkenes
B) alkynes
C) aromatics
D) alkanes
E) ketones


Answer: D
Diff: 1
Page Ref: Sec. 25.2


2) What general class of compounds is also known as olefins?

A) alkenes
B) alkynes
C) aromatics
D) alkanes
E) ketones


Answer: A
Diff: 1
Page Ref: Sec. 25.2


3) The simplest alkyne is __________.

A) ethylene
B) ethane
C) acetylene
D) propyne
E) benzene


Answer: C
Diff: 1
Page Ref: Sec. 25.2
Chemistry, 11e (Brown/LeMay/Bursten/Murphy)
The Chemistry of Life: Organic and Biological Chemistry
4) The melting and boiling points of hydrocarbons are determined by __________.



Answer: C
Diff: 1
Page Ref: Sec. 25.2


5) Hydrocarbons containing carbon-carbon triple bonds are called __________.

A) alkanes
B) aromatic hydrocarbons
C) alkynes
D) alkenes
E) olefins


Answer: C
Diff: 1
Page Ref: Sec. 25.2


6) Alkynes always contain a __________.

A) C=C bond
B) C≡C bond
C) C-C bond
D) C-H bond
E) C≡H bond


Answer: B
Diff: 1
Page Ref: Sec. 25.2
Chemistry, 11e (Brown/LeMay/Bursten/Murphy)
The Chemistry of Life: Organic and Biological Chemistry

7) Alkenes always contain a __________.

A) C=C bond
B) C≡C bond
C) C-C bond
D) C=H bond
E) C≡H bond


Answer: A
Diff: 1
Page Ref: Sec. 25.2


8) Hybridization of the carbon atom indicated by (*) in CH3 - ∗ CH 2 -CH3 , ∗ CH=CH 2 ,
and CH - ∗ C ≡ CH is __________, __________, and __________, respectively.
         3



A) sp3 ,sp 2 ,sp
B) sp3 ,sp,sp 2
C) sp,sp 2 ,sp3
D) sp,sp3 ,sp 2
E) sp 2 ,sp3 ,sp


Answer: A
Diff: 2
Page Ref: Sec. 25.2


9) The molecular geometry of each carbon atom in an alkane is __________.

A) octahedral
B) square planar
C) trigonal planar
D) tetrahedral
E) trigonal pyramidal


Answer: D
Diff: 1
Page Ref: Sec. 25.3
Chemistry, 11e (Brown/LeMay/Bursten/Murphy)
The Chemistry of Life: Organic and Biological Chemistry
10) The minimum number of carbons necessary for a hydrocarbon to form a branched
structure is __________.

A) 4
B) 6
C) 3
D) 9
E) 12


Answer: A
Diff: 1
Page Ref: Sec. 25.3


11) Cyclohexane has __________ fewer hydrogens than n-hexane.

A) 0
B) 1
C) 2
D) 3
E) 4


Answer: C
Diff: 1
Page Ref: Sec. 25.3


12) How many structural isomers of heptane exist?

A) 2
B) 4
C) 6
D) 8
E) 9
Answer: E
Diff: 3
Page Ref: Sec. 25.3
Chemistry, 11e (Brown/LeMay/Bursten/Murphy)
The Chemistry of Life: Organic and Biological Chemistry

13) The general formula of an alkane is __________.

A) C  H
    2n 2n + 2
B) C H
    n 2n
C) C H
    n 2n + 2
D) C H
    n 2n - 2
E) C H
    n n


Answer: C
Diff: 1
Page Ref: Sec. 25.3


14) Alkenes have the general formula __________.

A) C H
    n 2n
B) C H       .
    n 2n - 2
C) C H         .
    n 2n + 2
D) C H .
    n n
E) C H
    2n n


Answer: A
Diff: 1
Page Ref: Sec. 25.3
Chemistry, 11e (Brown/LeMay/Bursten/Murphy)
The Chemistry of Life: Organic and Biological Chemistry

15) The compound below is an __________.




A) alkyne
B) alkene
C) alkane
D) aromatic compound
E) olefin


Answer: A
Diff: 1
Page Ref: Sec. 25.3


16) What is the name of the compound below?




A) 2,4-methylbutene
B) 2,5-dimethylpentane
C) 2,4-ethylbutene
D) 2,4-dimethyl-1-pentene
E) 2,4-dimethyl-4-pentene


Answer: D
Diff: 1
Page Ref: Sec. 25.3
Chemistry, 11e (Brown/LeMay/Bursten/Murphy)
The Chemistry of Life: Organic and Biological Chemistry
17) Alkanes with __________ to __________ carbons are found in straight-run gasoline.

A) 2, 3
B) 5, 12
C) 1, 5
D) 9, 15
E) 20, 60


Answer: B
Diff: 1
Page Ref: Sec. 25.3


18) Gasoline and water do not mix because gasoline is __________.

A) less dense than water
B) less viscous than water
C) nonpolar and water is polar
D) volatile and water is not
E) polar and water is nonpolar


Answer: C
Diff: 1
Page Ref: Sec. 25.3


19) Which substance would be the most soluble in gasoline?

A) water
B) NaNO 3
C) HCl
D) hexane
E) NaCl


Answer: D
Diff: 1
Page Ref: Sec. 25.3
Chemistry, 11e (Brown/LeMay/Bursten/Murphy)
The Chemistry of Life: Organic and Biological Chemistry
20) Isooctane is assigned an octane number of 100, whereas __________ is assigned an
octane number of 0.

A) methane
B) propane
C) benzene
D) heptane
E) nitrous oxide


Answer: D
Diff: 2
Page Ref: Sec. 25.3




22) The name of CH 3 -CH=C=CH-CH-CH=CH-CH 3 is __________.

A) 2, 3, 5 - octatriene
B) 2, 5, 6 - octatriene
C) 2, 3, 6 - octatriene
D) 3, 5, 6 - octatriene
E) 3, 4, 7 - octatriene


Answer: C
Diff: 1
Page Ref: Sec. 25.3
Chemistry, 11e (Brown/LeMay/Bursten/Murphy)
The Chemistry of Life: Organic and Biological Chemistry
23) __________ could be the formula of an alkene.

A) C3 H 8
B) C3 H 6
C) C6 H 6
D) C17 H 36
E) CH8


Answer: B
Diff: 2
Page Ref: Sec. 25.3


24) In general, __________ are the most reactive hydrocarbons.

A) alkenes
B) alkynes
C) alkanes
D) cycloalkanes
E) olefins


Answer: B
Diff: 1
Page Ref: Sec. 25.3


25) The addition of HBr to 2-butene produces __________.

A) 1-bromobutane
B) 2-bromobutane
C) 1,2-dibromobutane
D) 2,3-dibromobutane
E) no reaction


Answer: B
Diff: 1
Page Ref: Sec. 25.3
Chemistry, 11e (Brown/LeMay/Bursten/Murphy)
The Chemistry of Life: Organic and Biological Chemistry

26) Aromatic hydrocarbons __________.

A) readily undergo addition reactions like alkenes
B) contain a series of π bonds on several consecutive carbon atoms
C) undergo substitution reactions more easily than saturated hydrocarbons
D) have sp 2 hybridized carbon atoms


Answer: B
Diff: 1
Page Ref: Sec. 25.3


27) How many hydroxyl groups are in a glycerol molecule?

A) 0
B) 1
C) 2
D) 3
E) 4


Answer: D
Diff: 1
Page Ref: Sec. 25.4


28) The general formula for an ether is __________.

A)
B)
C)
D)
E)


Answer: A
Diff: 1
Page Ref: Sec. 25.4
Chemistry, 11e (Brown/LeMay/Bursten/Murphy)
The Chemistry of Life: Organic and Biological Chemistry
29) Ethers can be made by condensation of two __________ molecules by splitting out a
molecule of water.

A) alkyne
B) alcohol
C) ketone
D) aldehyde
E) olefin


Answer: B
Diff: 1
Page Ref: Sec. 25.4


30) The general formula of an aldehyde is __________.

A)
B)
C)
D)
E)


Answer: D
Diff: 1
Page Ref: Sec. 25.4


31) The general formula of a carboxylic acid is __________.

A)
B)
C)
D)
E)


Answer: C
Diff: 1
Page Ref: Sec. 25.4
Chemistry, 11e (Brown/LeMay/Bursten/Murphy)
The Chemistry of Life: Organic and Biological Chemistry
32) The general formula of an ester is __________.

A)
B)
C)
D)
E)


Answer: E
Diff: 1
Page Ref: Sec. 25.4


33) CH 3CH 2 C(=O)NH 2 is called a(n) __________.

A) amine
B) amide
C) ketone
D) aldehyde
E) ester


Answer: B
Diff: 1
Page Ref: Sec. 25.4
Chemistry, 11e (Brown/LeMay/Bursten/Murphy)
The Chemistry of Life: Organic and Biological Chemistry
34) The compound below is a(n) __________.




A) carboxylic acid
B) ketone
C) aldehyde
D) ester
E) amine


Answer: D
Diff: 1
Page Ref: Sec. 25.4


35) The hybridization of the central carbon atom in an aldehyde is __________.

A) sp
B) sp3
C) sp 2
D) d 2sp3
E) sp 4


Answer: C
Diff: 1
Page Ref: Sec. 25.4
Chemistry, 11e (Brown/LeMay/Bursten/Murphy)
The Chemistry of Life: Organic and Biological Chemistry
39) Starch, glycogen, and cellulose are made of repeating units of __________.

A) lactose
B) glucose
C) fructose
D) sucrose
E) amino acids


Answer: B
Diff: 1
Page Ref: Sec. 25.8
Chemistry, 11e (Brown/LeMay/Bursten/Murphy)
The Chemistry of Life: Organic and Biological Chemistry




2) Which one of the following could be a cyclic alkane?

A) C5 H 5
B) C3 H 6
C) C4 H 6
D) C2 H 6
E) C9 H 20


Answer: B
Diff: 2
Page Ref: Sec. 25.3


3) If each of the following represents an alkane, and a carbon atom is located at each
vertex with the proper number of hydrogen atoms also bonded to it, which one is the
most reactive?

A)


B)


C)



D)


E)
They are all equally reactive since they are all alkanes.


Answer: D
Diff: 1
Page Ref: Sec. 25.3
Chemistry, 11e (Brown/LeMay/Bursten/Murphy)
The Chemistry of Life: Organic and Biological Chemistry

4) Pentane has __________ structural isomers.

A) 0
B) 1
C) 2
D) 3
E) 4


Answer: D
Diff: 2
Page Ref: Sec. 25.3
Chemistry, 11e (Brown/LeMay/Bursten/Murphy)
The Chemistry of Life: Organic and Biological Chemistry
5) Asphalt, isolated from petroleum, has a minimum of __________ carbon atoms.

A) 5
B) 12
C) 16
D) 20
E) 36


Answer: E
Diff: 2
Page Ref: Sec. 25.3


6) Which of the following is not currently used as an additive agent in gasoline?

A) toluene
B) ethanol
C) MTBE
D) tetraethyl lead


Answer: D
Diff: 1
Page Ref: Sec. 25.3


7) How many isomers are possible for C4 H10 ?

A) 1
B) 2
C) 3
D) 4
E) 10


Answer: B
Diff: 2
Page Ref: Sec. 25.3
Chemistry, 11e (Brown/LeMay/Bursten/Murphy)
The Chemistry of Life: Organic and Biological Chemistry
8) How many isomers are possible for C5 H12 ?

A) 1
B) 2
C) 3
D) 4
E) 10


Answer: C
Diff: 2
Page Ref: Sec. 25.3
Chemistry, 11e (Brown/LeMay/Bursten/Murphy)
The Chemistry of Life: Organic and Biological Chemistry
9) The structure of 2,3-dimethylheptane is __________.

A)




B)




C)




D)




E)




Answer: D
Diff: 1
Page Ref: Sec. 25.3
Chemistry, 11e (Brown/LeMay/Bursten/Murphy)
The Chemistry of Life: Organic and Biological Chemistry
10) When petroleum is distilled to separate the components by boiling point, the
component with the highest boiling point is called __________.

A) gas
B) gasoline
C) kerosene
D) paraffin
E) asphalt


Answer: E
Diff: 2
Page Ref: Sec. 25.3


11) What type of compound has been used to replace tetraethyl lead ((C 2 H 5 ) 4 Pb) as an
antiknock agent in gasoline?

A) aromatic compounds
B) olefins
C) fluorochlorocarbons
D) paraffins
E) oxygenated hydrocarbons


Answer: E
Diff: 1
Page Ref: Sec. 25.3
Chemistry, 11e (Brown/LeMay/Bursten/Murphy)
The Chemistry of Life: Organic and Biological Chemistry
13) How many isomers of C2 H 2 Cl2 are polar?

A) none
B) 1
C) 2
D) 3
E) It is impossible to tell without more information.


Answer: C
Diff: 1
Page Ref: Sec. 25.3


14) Which statement about hydrocarbons is false?

A) The smallest alkane to have structural (constitutional) isomers has 4 carbon atoms.
B) Cyclic alkanes are structural isomers of alkenes.
C) Alkanes are more reactive than alkenes.
D) Alkanes can be produced by hydrogenating alkenes.
E) Alkenes can be polymerized.


Answer: C
Diff: 1
Page Ref: Sec. 25.3


15) Which statement about addition reactions between alkenes and HBr is false?

A) The addition occurs at the double bond.
B) Bromine attacks the alkene carbon atom possessing a positive partial charge.
C) A hydrogen atom attaches itself to the alkene carbon atom possessing a negative
partial charge.
D) The π bond breaks in the course of the reaction.
E) The proposed mechanism involves radicals.


Answer: E
Diff: 1
Page Ref: Sec. 25.3
Chemistry, 11e (Brown/LeMay/Bursten/Murphy)
The Chemistry of Life: Organic and Biological Chemistry
16) Benzene behaves differently from a hydrocarbon which simply contains three C = C
bonds in that the latter would be expected to react much more readily with __________.

A) H 2
B) Cl2
C) Br2
D) HCl
E) all of the above


Answer: E
Diff: 1
Page Ref: Sec. 25.3
Chemistry, 11e (Brown/LeMay/Bursten/Murphy)
The Chemistry of Life: Organic and Biological Chemistry
18) Alcohols are hydrocarbon derivatives in which one or more hydrogens have been
replaced by a hydroxyl functional group. __________ is the general formula of an
alcohol.

A)
B)
C)
D)
E)


Answer: D
Diff: 1
Page Ref: Sec. 25.4


19) Which one of the following is not an alcohol?

A) acetone
B) glycerol
C) ethanol
D) cholesterol
E) ethylene glycol


Answer: A
Diff: 1
Page Ref: Sec. 25.4


20) The oxidation of ethanol produces __________.

A) acetic acid
B) formic acid
C) citric acid
D) lactic acid
E) oxalic acid


Answer: A
Diff: 2
Page Ref: Sec. 25.4
Chemistry, 11e (Brown/LeMay/Bursten/Murphy)
The Chemistry of Life: Organic and Biological Chemistry
21) The following reaction would produce a(n) __________.

                      R-OH + R'COOH →

A) ketone
B) ether
C) aldehyde
D) alcohol
E) ester


Answer: E
Diff: 2
Page Ref: Sec. 25.4


22) Which one of the following compounds is an isomer of CH 3CH 2 CH 2 CH 2 OH ?

A) CH 3CH 2 CH 2 OH

B)



C)




D)




E) CH 3OH


Answer: D
Diff: 1
Page Ref: Sec. 25.4
Chemistry, 11e (Brown/LeMay/Bursten/Murphy)
The Chemistry of Life: Organic and Biological Chemistry
23) What is the general formula for a ketone?

A)
B)
C)
D)
E)


Answer: B
Diff: 1
Page Ref: Sec. 25.4


24) Which of the following compounds do not contain an sp3 hybridized oxygen atom?

A) ketones
B) alcohols
C) ethers
D) esters
E) water


Answer: A
Diff: 1
Page Ref: Sec. 25.4
Chemistry, 11e (Brown/LeMay/Bursten/Murphy)
The Chemistry of Life: Organic and Biological Chemistry
25) Of the compounds below, __________ is an isomer of




A)




B)




C)




D)




E)




Answer: A
Diff: 1
Page Ref: Sec. 25.4
Chemistry, 11e (Brown/LeMay/Bursten/Murphy)
The Chemistry of Life: Organic and Biological Chemistry



26) Which structure below represents a ketone?
A)


B)




C)




D)




E)




Answer: D
Diff: 1
Page Ref: Sec. 25.4
Chemistry, 11e (Brown/LeMay/Bursten/Murphy)
The Chemistry of Life: Organic and Biological Chemistry

27) Which structure below represents an aldehyde?

A)


B)




C)




D)




E)




Answer: C
Diff: 1
Page Ref: Sec. 25.4
Chemistry, 11e (Brown/LeMay/Bursten/Murphy)
The Chemistry of Life: Organic and Biological Chemistry

28) Which structure below represents an ether?

A)


B)




C)




D)




E)




Answer: A
Diff: 1
Page Ref: Sec. 25.4
Chemistry, 11e (Brown/LeMay/Bursten/Murphy)
The Chemistry of Life: Organic and Biological Chemistry
29) Which of the following compounds does not contain a C = O bond?

A) ketones
B) aldehydes
C) esters
D) amides
E) ethers


Answer: E
Diff: 1
Page Ref: Sec. 25.4
Chemistry, 11e (Brown/LeMay/Bursten/Murphy)
The Chemistry of Life: Organic and Biological Chemistry
Chemistry, 11e (Brown/LeMay/Bursten/Murphy)
The Chemistry of Life: Organic and Biological Chemistry
36) Which of the following contains a peptide linkage?

A)




B)




C)



D)



E) none of the above


Answer: A
Diff: 1
Page Ref: Sec. 25.7
Chemistry, 11e (Brown/LeMay/Bursten/Murphy)
The Chemistry of Life: Organic and Biological Chemistry
37) Sugars are examples of what type of molecule?

A) proteins
B) carbohydrates
C) nucleic acids
D) amino acids
E) salts


Answer: B
Diff: 1
Page Ref: Sec. 25.8


38) __________ is a disaccharide.

A) Glucose
B) Galactose
C) Sucrose
D) Ribose
E) Fructose


Answer: C
Diff: 1
Page Ref: Sec. 25.8


39) __________ is a monosaccharide.

A) Sucrose
B) Maltose
C) Glucose
D) Lactose


Answer: C
Diff: 1
Page Ref: Sec. 25.8
Chemistry, 11e (Brown/LeMay/Bursten/Murphy)
The Chemistry of Life: Organic and Biological Chemistry
40) The principal difference between fructose and glucose is that __________.

A) fructose is a disaccharide and glucose is a monosaccharide
B) fructose is a monosaccharide and glucose is a disaccharide
C) fructose is chiral and glucose is not
D) glucose is chiral and fructose is not
E) fructose is a ketone sugar and glucose is an aldehyde sugar


Answer: E
Diff: 1
Page Ref: Sec. 25.8


41) Which one of the following is a monosaccharide?

A) fructose
B) lactose
C) sucrose
D) maltose
E) none of the above


Answer: A
Diff: 1
Page Ref: Sec. 25.8
Chemistry, 11e (Brown/LeMay/Bursten/Murphy)
The Chemistry of Life: Organic and Biological Chemistry


25.3 Short Answer Questions

1) Electron pairs surrounding the carbon atoms in alkanes are in a __________
arrangement.


Answer: tetrahedral
Diff: 1
Page Ref: Sec. 25.1


Diff: 1
Page Ref: Sec 25.3
Chemistry, 11e (Brown/LeMay/Bursten/Murphy)
The Chemistry of Life: Organic and Biological Chemistry
3) Rotation around a carbon-carbon double bond is difficult, requiring energy but it is a
key process in the chemistry of __________.


Answer: vision
Diff: 1
Page Ref: Sec 25.3


4) Why is cyclopropane more reactive than propane?


Answer: the small ring of cyclopropane forces the C-C-C bond angle to be significantly
less than 109.5 ° of __________ the tetrahedral structure of C in propane.
Diff: 1
Page Ref: Sec. 25.3


5) Write the formula for 2-methyl-4-propylnonane.


Answer:




Diff: 1
Page Ref: Sec. 25.3


6) What is the correct name for the compound, CH 3 CH 2 CH = CHCH 2 CH = CHCH 3 ?


Answer: 2,5-octadiene
Diff: 1
Page Ref: Sec. 25.3
Chemistry, 11e (Brown/LeMay/Bursten/Murphy)
The Chemistry of Life: Organic and Biological Chemistry
7) What is the name of the compound below?




Answer: 4,6-dimethyl-1-heptyne
Diff: 1
Page Ref: Sec. 25.3




10) Predict the product of the catalytic hydrogenation of 6-ethyl-3-decene.


Answer: 6-ethyldecane
Diff: 1
Page Ref: Sec. 25.3


11) Hydrogenation of what alkyne produces propane?


Answer: propyne
Diff: 1
Page Ref: Sec. 25.3
Chemistry, 11e (Brown/LeMay/Bursten/Murphy)
The Chemistry of Life: Organic and Biological Chemistry
12) In the reaction of nitric acid with benzene, which isomer is formed when a second
nitro group is substituted?


Answer: meta
Diff: 1
Page Ref: Sec. 25.3


13) The addition of an alkyl halide to an aromatic ring compound is called the
__________ reaction.


Answer: Freidel-Crafts
Diff: 1
Page Ref: Sec. 25.3


14) What is the name of the compound below?




Answer: 4-propyloctane
Diff: 1
Page Ref: Sec. 25.3


15) The anaerobic conversion of carbohydrates to ethanol is driven by the presence of
__________.


Answer: yeast
Diff: 1
Page Ref: Sec. 25.4
Chemistry, 11e (Brown/LeMay/Bursten/Murphy)
The Chemistry of Life: Organic and Biological Chemistry
16) What is the name of the compound CH 3 CH 2 CH(OH)CH 2 CH 2 CH 3 ?


Answer: 3-hexanol
Diff: 1
Page Ref: Sec. 25.4


17) The formation of aspirin by reacting salicylic acid with acetic acid is a __________
reaction.


Answer: condensation
Diff: 2
Page Ref: Sec. 25.4


18) In the oxidation of ethanol the intermediate formed is __________.


Answer: acetaldehyde
Diff: 1
Page Ref: Sec. 25.4


19) The primary ingredient in vinegar is __________


Answer: acetic acid
Diff: 1
Page Ref: Sec. 25.4


20) The aromas of different fruit are due to the chemical compounds known as
__________.


Answer: esters
Diff: 1
Page Ref: Sec. 25.4
Chemistry, 11e (Brown/LeMay/Bursten/Murphy)
The Chemistry of Life: Organic and Biological Chemistry
21) The hydrolysis of an ester in the presence of a base is called __________.


Answer: saponification
Diff: 1
Page Ref: Sec. 25.4




28) The condensation reaction of a carboxyl group of one amino acid and the amino
group of a second amino acid results in the formation of a __________.


Answer: peptide bond
Diff: 1
Page Ref: Sec. 25.7
Chemistry, 11e (Brown/LeMay/Bursten/Murphy)
The Chemistry of Life: Organic and Biological Chemistry




3) The stability of benzene is a major function of delocalized π bonding.
Answer: True

Diff: 1
Page Ref: Sec. 25.3


4) Aldehydes are less reactive than ketones.
Answer: False

Diff: 1
Page Ref: Sec. 24.4
Chemistry, 11e (Brown/LeMay/Bursten/Murphy)
The Chemistry of Life: Organic and Biological Chemistry
5) A carbon with three or more attached groups will be chiral.
Answer: False

Diff: 1
Page Ref: Sec. 25.5


6) Racemic mixtures of enantiomers do not rotate the plane of polarized light.
Answer: True

Diff: 1
Page Ref: Sec. 25.5


7) The majority of glucose molecules exist in ring structure.
Answer: True

Diff: 1
Page Ref: Sec. 25.8


8) Humans digest starch but not cellulose because of differences in the type of linkage
between the glucose monomers of these substances
Answer: True

Diff: 1
Page Ref: Sec. 25.8


9) The DNA double helix is held together by hydrogen bonds and London dispersion
forces.
Answer: True

Diff: 1
Page Ref: Sec. 25.10

				
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