21. Aldehydes and Ketones: Nucleophilic Addition

What are the products of the following reactions?

e.

f.

Show what amines and carbonyl compounds combine to give the following derivatives.

(f)

Propose a mechanism for the acid-catalyzed reaction of cyclohexanone with pyrrolidine.

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.

Give the structures of the carbonyl compound and the amine used to form the following imines.

(a)

(b)

(c)

The nucleosides that make up DNA have heterocyclic rings linked to deoxyribose by an aminoacetal functional group. Point out the aminoacetal linkages in deoxycytidine and deoxyadenosine.

Show how you would synthesize octanal from each compound. You may use any necessary reagents.

(a) octan-1-ol

Predict the products formed when cyclohexanecarbaldehyde reacts with the following reagents.

(a) PhMgBr, then H₃O⁺

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

(a)

Propose a mechanism for each of the following reactions:

a.

Which of the following are a. hemiacetals? b. acetals? c. hydrates?

2.

Predict the products of the following reactions:

(g)

Show what alcohols and carbonyl compounds give the following derivatives.

(a)

(b)

(c)

What starting materials are required to synthesize the following compounds, using the Fischer indole synthesis?

c.