Chemistry Department

 

University of Alberta

 

CHEM 263 B6

 

Final Exam

 

April 26, 2007

 

  1. Name five (5) of the following structures:

 

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  1. Give the structural formula of five (5) of the following compounds. Where given, complete the partial structures:

 

    1. L-serine

 

 

    1. (R)-1-bromoethyl butanoate

 

 

    1. (2Z,6R)-6-ethoxy-2-methyl-2-heptenamide

 

         

 

 

    1. (S)-2-hydroxy-3-methylbutanenitrile

 

                                            

 

    1. a-D-glucopyranose

                       

 

    1. (S)-4-hydroxy-4-methyl-2-hexanone

 

                       

 

  1. Give the structure(s) of the principle organic products of  ten (10) of the following reactions:

 

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  1. What reagent(s) would you use to effect ten (10) of the following conversions?

 

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  1. Provide synthetic pathways for three (3) of the following transformations:

 

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  1. The IR and 1H NMR spectra of a compound of molecular formula C9H8O are given below.  Propose a structure for this compound:

 

SDBSWeb: http://www.aist.go.jp/RIODB/SDBS/ (12-04-07)

 

 

  1.  
    1. What is meant by the term epimer?                       

 

    1. Methyl a-D-glucopyranoside reacts with aqueous acid to form b-D-glucose:

 

 

Propose a mechanism that accounts for this transformation.

 

  1.  

 

a.      Explain what is meant by the term essential amino acid.

 

b.      Explain the term isoelectric point.

 

c.      The isoelectric point of tryptophan is 5.9.  What is the structure of this acid at pH 2.0? (You do not need to specify any stereochemistry about C-2)

 

 

d.      In spite of having two nitrogen functions, tryptophan is a neutral amino acid. Provide an explanation.       

 

  1. Butanamine reacts with sodium nitrite and hydrochloric acid to form nitrogen and the following mixture: 1-butanol (25%), 2-butanol (13%), 1-butene and 2-butene (37%), 1-chlorobutane (5%), and 2-chlorobutane (3%).

 

a.      What is the most likely intermediate common to all of these products? It is formed at the same time that the nitrogen is produced.

 

b.      Propose a mechanism that accounts for its conversion into 2-butanol.

 

  1.  3-Cyclohexenone rapidly equilibrates with 2-cyclohexenone on treatment with dilute sulfuric acid. Propose a mechanism for the acid-catalyzed transformation of 3-cyclohexenone to form 2-cyclohexenone:

 

  1.  Propose a mechanism for the following reaction:

 

 

  1. Match the pKa values, -10, 2.9,  3.77, 4.76, 15.5, 19.3, 24, and 46 to the appropriate structure:

 

           

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Updated June 18, 2007