Draw a structure for each of the following:

d. propanenitrile

Draw a structure for each of the following:

g. benzoic anhydride

Draw a structure for each of the following:

i. 3-methylbutanenitrile

Draw a structure for each of the following:

j. cycloheptanecarboxylic acid

Name the following:

a.

Name the following:

c.

Name the following:

e.

Name the following:

f.

What compounds are formed from the reaction of benzoyl chloride with the following reagents?

a. sodium acetate

b. water

What compounds are formed from the reaction of benzoyl chloride with the following reagents?

e. aqueous NaOH

What compounds are formed from the reaction of benzoyl chloride with the following reagents?

f. cyclohexanol

What compounds are formed from the reaction of benzoyl chloride with the following reagents?

g. excess benzylamine

h. 4-chlorophenol

What compounds are formed from the reaction of benzoyl chloride with the following reagents?

i. isopropyl alcohol

What compounds are formed from the reaction of benzoyl chloride with the following reagents?

k. potassium formate

What compounds are obtained from the following hydrolysis reactions?

c.

What compounds are obtained from the following hydrolysis reactions?

d.

Because bromocyclohexane is a secondary alkyl halide, both cyclohexanol and cyclohexene are formed when the alkyl halide reacts with hydroxide ion. Suggest a method to synthesize cyclohexanol from bromocyclohexane that forms little or no cyclohexene.

a. Which compound would you expect to have a greater dipole moment, methyl acetate or butanone?

b. Which would you expect to have a higher boiling point?

Using an alcohol for one method and an alkyl halide for the other, show two ways to make each of the following esters:

d. methyl phenylethanoate (odor of honey)

What reagents would you use to convert methyl propanoate to the following compounds?

a. isopropyl propanoate

b. sodium propanoate

What reagents would you use to convert methyl propanoate to the following compounds?

c. N-ethylpropanamide

d. propanoic acid

What products would you expect to obtain from the following reactions?

a. malonic acid + 2 acetyl chloride

What products would you expect to obtain from the following reactions?

b. methyl carbamate + methylamine

What products would you expect to obtain from the following reactions?

c. urea + water

d. β-ethylglutaric acid + acetyl chloride + Δ

A compound with molecular formula C₅H₁₀O₂ gives the following IR spectrum. When it undergoes acid-catalyzed hydrolysis, the compound with the ¹H NMR spectrum shown below is formed. Identify the compounds.

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Aspartame, the sweetener used in the commercial products NutraSweet and Equal, is 200 times sweeter than sucrose. What products will be obtained if aspartame is hydrolyzed completely in an aqueous solution of HCl?

a. Which of the following reactions does not give the carbonyl product shown?

b. Which of the reactions that do not occur can be made to occur if an acid catalyst is added to the reaction mixture?

9.

10.

a. Which of the following reactions does not give the carbonyl product shown?

b. Which of the reactions that do not occur can be made to occur if an acid catalyst is added to the reaction mixture?

5.

Describe how the target molecule (butanone) can be synthesized in a high yield from butane.

1,4-Diazabicyclo[2.2.2]octane (abbreviated DABCO) is a tertiary amine that catalyzes transesterification reactions. Explain how it does this.