Name the following:

a.

Name the following:

c.

Name the following:

e.

Name the following:

g.

Name the following:

h.

Name the following:

i.

Draw the structure for each of the following:

a. phenyl acetate

Draw the structure for each of the following:

b. γ-caprolactam

Draw the structure for each of the following:

e. γ-methylcaproic acid

Draw the structure for each of the following:

f. β-bromobutyramide

Draw the structure for each of the following:

g. ethyl 2-chloropentanoate

Draw the structure for each of the following:

h. cyclohexanecarbonyl chloride

Draw the structure for each of the following:

i. α-chlorovaleric acid

Which is longer, the carbon–oxygen single bond in a carboxylic acid or the carbon–oxygen bond in an alcohol? Why?

There are three carbon–oxygen bonds in methyl acetate.

a. What are their relative bond lengths?

b. What are the relative infrared (IR) stretching frequencies of these bonds?

Which is a correct statement?

A. The delocalization energy of an ester is about 18 kcal/mol, and the delocalization energy of an amide is about 10 kcal/mol.

B. The delocalization energy of an ester is about 10 kcal/mol, and the delocalization energy of an amide is about 18 kcal/mol.

What reagent should be used to carry out the following reaction?

b. What is the product of the reaction of acetamide with HO⁻? The pK_a of NH₃ is 36; the pK_a of H₂O is 15.7.

What is the product of an acyl substitution reaction—a new carboxylic acid derivative, a mixture of two ­carboxylic acid derivatives, or no reaction—if the new group in the tetrahedral intermediate is the following? a. a stronger base than the substituent that is attached to the acyl group

What is the product of an acyl substitution reaction—a new carboxylic acid derivative, a mixture of two ­carboxylic acid derivatives, or no reaction—if the new group in the tetrahedral intermediate is the following? b. a weaker base than the substituent that is attached to the acyl group

Using the pK_a values listed in [TABLE 15.1], predict the products of the following reactions:

c.

Using the pKa values listed in [TABLE 15.1], predict the products of the following reactions:

d.

Starting with acetyl chloride, what neutral nucleophile would you use to synthesize each of the following compounds?

c.

Starting with acetyl chloride, what neutral nucleophile would you use to synthesize each of the following compounds?

d.

Starting with acetyl chloride, what neutral nucleophile would you use to synthesize each of the following compounds?

e.

Starting with acetyl chloride, what neutral nucleophile would you use to synthesize each of the following compounds?

f.

Write the mechanism for each of the following reactions:

a. the reaction of acetyl chloride with water to form acetic acid

Write the mechanism for each of the following reactions:

b. the reaction of benzoyl chloride with excess methylamine to form N-methylbenzamide

Starting with methyl acetate, what neutral nucleophile would you use to synthesize each of the following compounds? a. ethyl acetate

Starting with methyl acetate, what neutral nucleophile would you use to synthesize each of the following compounds? b. acetamide