CHEM 210 Study Guide Exam 4 2010

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CHEM 210 Study Guide Exam 4 2010 Powered By Docstoc
					Exam 4 - Study Guide
CHEM 210
CHAPTER 9: Alcohols, Ethers and Epoxides
     1. Nomenclature – know how to name simple alcohols, ethers and epoxides
            a. What is an alcohol, enol or phenol?
            b. What are ethers and epoxides?
     2. Acid-base properties
            a. What is the pKA of a typical alcohol? How does this compare to water?
            b. With which reagents/bases would you use to deprotonate an alcohol?
            c. What is an oxonium ion? How does this compare to hydronium?
     3. Preparation of Alcohols, Ethers and Epoxides
            a. Review preparation of alcohols by SN1 and SN2 reactions
            b. Know the Williamson Ether synthesis and selecting the best route
            c. Know how epoxides are made from halohydrins – intramolecular Williamson ether synth.
     4. Reactions of Alcohols
            a. Dehydration of alcohols to alkenes
                       i. What reagents/conditions are used (know use of TsOH)
                                                         o   o     o
                      ii. What are the mechanisms for 1 , 2 or 3 alcohols
                     iii. What alkene is the major product
                    iv. What reaction from Chapter 10 is this in equilibrium with?
                      v. Carbocation rearrangements – know the mechanism and where to look for them –
                               4 next to 2 C  1,2-alkyl shift
                                   o         o  +

                               3 next to 2 C  1,2-hydride shift
                                   o         o  +

            b. Dehydration of alcohols with POCl3/pyridine
                       i. What alcohols work best by this method?
                      ii. What is the mechanism? Does the mechanism differ for different alcohols?
                     iii. Are rearrangements possible?
            c. Conversion of alcohols to alkyl halides with HX
                       i. What alcohols work best?
                      ii. What is the mechanism? Does the mechanism differ for different alcohols?
                     iii. Are rearrangements possible? For which alcohols?
                    iv. Is stereochemistry important? For which alcohols?
            d. Conversion of alcohols to alkyl chlorides with SOCl2 and alkyl bromides with PBr3
                       i. What are the conditions used?
                      ii. What alcohols work best?
                     iii. What is the mechanism? Does the mechanism differ for different alcohols?
                    iv. Is stereochemistry important? What is the starting vs. final configuration?
            e. Conversion of alcohols to alkyl tosylates
                       i. What is tosylate? How good of a leaving group is it?
                      ii. What is the mechanism for its formation?
                     iii. What happens to the stereochemistry of the alcohol when converted to the tosylate?
            f. Reaction of ethers with strong acids
                       i. Why are ethers unreactive?
                      ii. Why are reactions of ethers not synthetically useful when they do occur?
                     iii. What are the products of the reaction of ether with strong acids?
            g. Reaction of epoxides with strong nucleophiles or with acids
                       i. What is the mechanism for each?
                      ii. What is the stereochemistry of each reaction?
                     iii. What is the regiochemistry of each reaction (i.e. where does nucleophile attack to open the
                          ring?

CHAPTER 10: Alkenes
     5. Nomenclature – know how to name simple alkenes
            a. Which alkenes are named by cis- and trans- nomenclature? How is it done?
            b. Which alkenes are named by E and Z nomenclature? How is it done?
     6. Structure – Review the bonding model and hybridization of alkenes, reactivity of  bond
     7. Preparation of Alkenes
            a. Review preparation of alkenes by E1 and E2 reactions
            b. Review dehydration of alcohol methods from above
        8. Reactions of Alkenes
              a. Addition Reactions
                        i. What are the general features of an addition reaction?
                       ii. What general reaction is it opposite to?
              b. Hydrohalogenation
                        i. Know the general reaction and reagents used
                       ii. Know the mechanism/stereochemistry and intermediates
                      iii. Know the energetics
                      iv. Be able to apply Markovnikov’s Rule for the regiochemistry of the products
              c. Hydration
                        i. Know the general reaction and reagents used
                       ii. Know the mechanism/stereochemistry and intermediates (similar to hydrohalogenation)
                      iii. Apply Markovnikov’s Rule
                      iv. Know what reaction from above this is a complement to
                       v. Know that small alcohols can be used rather than water to make ethers
              d. Halogenation
                        i. Know the general reaction and reagents used
                       ii. Know how the mechanism and how it differs from 8 b. and 8 c.
                      iii. Know the stereochemical outcome of the reaction/Markovnikov’s Rule
                      iv. Know which halogens react
              e. Halohydrin formation
                        i. Know the general reaction and reagents used
                       ii. Know how it is similar and different from halogenation
                      iii. Why are the products useful?
              f. Hydroboration/Oxidation
                        i. Know the reaction and reagents used
                       ii. Know the mechanism, and why the products are anti-Markovnikov
                      iii. Know the stereochemical outcome of the reaction

CHAPTER 11: Alkynes
     1. Nomenclature – be able to name simple internal and terminal alkynes
     2. Review the general features of alkynes – bonding, hybridization, etc.
     3. Know the acid-base chemistry of terminal alkynes
            a. What bases are used to deprotonate them?
            b. What can be done with the anions formed?
     4. Review the synthesis of alkynes – geminal or vicinal dihalides + base
     5. Addition reactions of Alkynes – know how alkynes are similar/different to alkenes in reactivity
            a. Hydrohalogenation
                  i. Know the general reaction and reagents used
                 ii. Know the mechanism and intermediates
                iii. Recognize the proper regiochemistry of the products
            b. Halogenation
                  i. Know the general reaction and reagents used
                 ii. Know the mechanism and intermediates
                iii. Recognize the proper regiochemistry of the products
            c. Hydration
                  i. Know the general reaction and reagents used
                 ii. Know the mechanism and intermediates
                iii. Recognize the proper regiochemistry of the products
                iv. How are the products different from alkene hydration
                 v. What is a tautomer?
            d. Hydroboration-Oxidation
                  i. Know the general reaction and reagents used
                 ii. Know the mechanism and intermediates
                iii. Recognize the proper regiochemistry of the products
                iv. How are the products different from alkene hydration
                 v. What is a tautomer?

Disclaimer – a study guide is simply that – a guide to help you outline and organize your preparation for the
exam. There may be material on the exam not explicitly mentioned here that will be used to test your application
of knowledge. Remember you will be required to complete chemical reactions – predicting the products or
indicate the starting materials used. This set of chapters has more reactions than you have seen before!

				
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