Propose a mechanism for each of the following reactions:

b. <IMAGE>

Show what amines and carbonyl compounds combine to give

the following derivatives.

(e) <IMAGE>

Propose mechanisms for the following reactions.

(b) <IMAGE of reaction>

Show a complete mechanism for this equilibrium established in diethyl ether with HCl gas as catalyst.

<IMAGE of reaction>

Depending on the reaction conditions, two different imines of formula C8H9N might be formed by the reaction of benzaldehyde with methylamine. Explain, and give the structures of the two imines.

For each compound,

1. name the functional group.

2. show what compound(s) result from complete hydrolysis.

(g) <IMAGE>

For each compound,

1. name the functional group.

2. show what compound(s) result from complete hydrolysis.

(h) <IMAGE>

Show how you would synthesize the following derivatives

from appropriate carbonyl compounds.

(b) <IMAGE>

Identify the bonds broken and formed in the following addition reaction.

(a) Would you expect this reaction to be favored based on entropy?

(b) Based on enthalpy [qualitatively]?

(c) Overall?

<IMAGE>

Suggest a carbonyl to react with NaCN/HCN to produce the following cyanohydrins.

(a) <IMAGE>

How would you synthesize the cyanohydrin shown? (See Chapter 17 for a review.)

<IMAGE>

(••) LOOKING AHEAD CHAPTERS 8, 17 In Chapters 8 and 17 we learn two reaction for the synthesis of the alcohol shown. (a) Show a mechanism for each of the reactions. (b) If you were designing a synthetic route, which would be considered more sustainable? Consider all factors. [Assume the starting organic molecules are equally green.]

<IMAGE>

<IMAGE>

Predict the major products of the following reactions.

(e) <IMAGE of reaction>

(••••) As discussed in Section 17.9.1, alkenes can be hydrogenated selectively in the presence of ketones. Suppose that was not the case, and suggest how you might use a protecting group strategy to generate A from B.

<IMAGE>

Show how you would synthesize the following derivatives

from appropriate carbonyl compounds.

(d) <IMAGE>

Acetals can serve as protecting groups for 1,2-diols, as well as for aldehydes and ketones. When the acetal is formed from acetone plus the diol, the acetal is called an acetonide. Show the acetonides formed from these diols with acetone under acid catalysis.

<IMAGE>

Acetals can serve as protecting groups for 1,2-diols, as well as for aldehydes and ketones. When the acetal is formed from acetone plus the diol, the acetal is called an acetonide. Show the acetonides formed from these diols with acetone under acid catalysis.

<IMAGE>

Show what amines and carbonyl compounds combine to give

the following derivatives.

(d) <IMAGE>

Show what amines and carbonyl compounds combine to give

the following derivatives.

(f) <IMAGE>

Draw structures of the following derivatives.

(a) the 2,4-dinitrophenylhydrazone of benzaldehyde

Draw structures of the following derivatives.

(b) the semicarbazone of cyclobutanone

Draw structures of the following derivatives.

(c) cyclopropanone oxime

Predict the products formed when cyclohexanone reacts with the following reagents. (e) phenylhydrazine and weak acid

What are the products of the following reactions?

b. <IMAGE>

Suggest a series of steps involving a cuprate reagent that would convert the reactant on the left to the product on the right. The ideal number of steps is shown.

(b) <IMAGE>

What is the specific rotation of an equilibrium mixture of fructose? (Hint: Recall that the specific rotation of an equilibrium mixture of glucose is + 52.7.)

Propose mechanisms for the following reactions. (e) <IMAGE of reaction>

Propose mechanisms for the following reactions.

(e) <IMAGE>