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Carboxylic Acid Derivatives

Please see the attached file for the fully formatted problems.

1. Which one of the following is the least effective method for the synthesis of the compound shown?

a. treat trans-4-tert-butylcyclohexanol with sodium acetate
b. combine trans-4-tert-butylcyclohexanol and acetic anhydride in the presence of pyridine
c. combine trans-4-tert-butylcyclohexanol and acetyl chloride in the presence of pyridine
d. dissolve trans-4-tert-butylcyclohexanol in acetic acid containing a few drops of H2SO4

2. The behaviors of acyl chlorides and aldehydes in a reaction with a nucleophile are different because:

a. The carbonyl carbon of the aldehyde is more positive.
b. The bulky chlorine sterically hinders nucleophilic attack at the carbonyl group - I'm totally guessing
c. The acyl chloride cannot form a tetrahedral intermediate
d. There is a good leaving group in the acyl chloride
e. The aldehyde has a readily oxidizable hydrogen
3. What is the product of the following reaction?

a. 1
b. 2
c. 3
d. 4
e. 5
4. The tetrahedral intermediate in the Fischer esterification of formic acid (HCO2H) with 1-butanol has the structure:

a. 1
b. 2
c. 3
d. 4
5. For the reaction performed in basic solution, which one of the following tetrahedral intermediates is most likely to dissociate to an ester?

a. 1
b. 2
c. 3
d. 4
6. Reaction of benzoic acid with CH318OH in the presence of an acid catalyst yields:

a. 1
b. 2
c. 3
d. 4
7. Which of the following species is not an intermediate in the generally accepted mechanism for the reaction shown?

a. 1
b. 2
c. 3
d. 4
e. 5
8. Which one of the following is the most effective method for the synthesis of the compound shown?

a. treat trans-4-tert-butylcyclohexanol with sodium acetate
b. treat trans-1-bromo-4-tert-butylcyclohexane with sodium acetate
c. combine trans-4-tert-butylcyclohexanol and acetic anhydride in the presence of pyridine
d. combine cis-4-tert-butylcyclohexanol and acetyl chloride in the presence of pyridine
9. Hydrolysis of ethyl acetate in aqueous base proceeds by attack of:

a. 1
b. 2
c. 3
d. 4
e. 5
10. Which structure corresponds to the tetrahedral intermediate formed during the reaction of an ester with an amine?
a. 1
b. 2 - I'm totally guessing
c. 3
d. 4
e. 5

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This solution explains how to solve several problems dealing with carboxylic acid derivatives.

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