Organic Chemistry III
	Professor Carl C. Wamser
Chem 336 - Spring 2006	Exam 1 Answer Key

1. (15 points) Give complete names for each of the following:

a)

4-cyclooctenyl (S)-3-methylpentanoate

b)

(S)-N-methyl-N-(1-methylpropyl)-5-methyl-5-hexenamide

c)

(E)-7-bromo-3-methyl-5-oxo-2-heptenoyl bromide

2. (15 points) Give complete structures for each of the following:

a) p-cyanobenzoyl chloride

b) isobutyl cyclopentanecarboxylate

c) hexanedioic anhydride

d) the best resonance form for the enolate of malonic ester

e) N-cyclobutyl-N-methylformamide

3. (15 points) Indicate the relative order of the following series of compounds with respect to the property listed. Write “MOST” and “LEAST” under the compounds with the highest and lowest values, respectively.

a) acidity

MIDDLE / / LEAST / / MOST

b) acidity

MIDDLE / / LEAST / / MOST

c) basicity

MIDDLE / / MOST / / LEAST

d) ease of hydrolysis

MIDDLE / / LEAST / / MOST

e) ease of decarboxylation

MOST / / MIDDLE / / LEAST

4. (15 points) Complete the following table for the reactions indicated.

a) ester hydrolysis ( RCOOR’ + H2O )

neutral tetrahedral intermediate

conjugate base of tetrahedral intermediate

conjugate acid of tetrahedral intermediate
(two different forms)

or

final products

b) amide hydrolysis ( RCONHR’ + H2O )

neutral tetrahedral intermediate

conjugate base of tetrahedral intermediate

conjugate acid of tetrahedral intermediate
(two different forms)

or

final products

c) amide formation from an acid chloride ( RCOCl + NH3 )

neutral tetrahedral intermediate

conjugate base of tetrahedral intermediate

conjugate acid of tetrahedral intermediate
(two different forms)

or or

final products

5. (15 points) Complete each of the following reactions by adding the major product.

a)

b)

c)

d)

e)

6. (15 points) The following retrosynthetic analysis was developed for the preparation of valine, an amino acid. Show all the steps that would be needed in the synthesis, starting from acetone and ethyl acetate.

7. (10 points) The malonic ester synthesis can be modified by using an epoxide instead of an alkyl halide, in which case a lactone is formed.
Show a complete mechanism for just the first stage of the synthesis (up to the enolate anion shown in brackets below). Show all steps and show all resonance forms for any intermediates involved.