21. Aldehydes and Ketones: Nucleophilic Addition

Predict the products of the following reactions.

(e) product of (c) + DIBAL-H, then hydrolysis

Why can't diisobutylaluminum hydride (iBu₂AlH, DIBAL-H) reduce an aldehyde, but it can reduce an ester?

Predict the major products of the following reactions.

(c)

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

(d) 1-bromoheptane

Show how you would accomplish the following synthetic conversions efficiently and in good yield. You may use any necessary additional reagents and solvents.

(f)

Show how you would accomplish the following synthetic conversions efficiently and in good yield. You may use any necessary additional reagents and solvents.

(c)

Predict the major products of the following reactions.

(b)

Predict the product of the following reaction sequences.

(b)

When the ester attacked the aluminum of DIBAl-H, why did the carbonyl oxygen attack preferentially over the alkoxy oxygen?

The esters shown differ only by the alkoxy group.

(i) Predict the product(s) obtained when these react with DIBAl-H.

(ii) Based on your answer, in a sequence like this, would there ever be a need to convert from one ester to another?

(b)

Predict the products of the following reactions:

(e)

(f)