Question

PROBLEM 18-10

Predict the products of the following reactions:

Short answer

LiAlH₄ is a strong reducing agent that reduces aldehydes, ketones, acid chlorides to alcohol by donation of hydride ion (H^-). LiAlH(O-t-Bu)₃ is a mild reducing agent that reduces acid chloride to aldehyde instead of alcohol. DIBAL-H is also a reducing agent that reduces esters to aldehyde by donation of hydride ion (H^-).

Step-by-step solution

Detailed Answer:Step 1: Theory of LiAlH4, LiAlH(O-t-Bu)3, and DIBAL-H

LiAlH₄ is a strong reducing agent that reduces aldehydes, ketones, acid chlorides to alcohol by donation of hydride ion (H^-). LiAlH(O-t-Bu)₃ is a mild reducing agent that reduces acid chloride to aldehyde instead of alcohol. DIBAL-H is also a reducing agent that reduces esters to aldehyde by donation of hydride ion (H^-).

Detailed answer for part (a)

LiAlH₄ is a strong reducing agent that reduces acid chloride that is benzoyl chloride to alcohol that is benzyl alcohol by donation of hydride ion (H^-).

Detailed answer for part (b)

LiAlH(O-t-Bu)₃ is a mild reducing agent that reduces benzoyl chlorideto benzaldehyde.

Detailed answer for part (c)

The organic part attached to copper is a vinyl anion that attacks the carbonyl carbon once to form the product as shown in the image:

Detailed answer for part (d)

The organic part attached to magnesium is aallyl anion that attacks the carbonyl carbon twice as it is present in excess, followed by workup with water to form the alcohol as shown in the image:

Detailed answer for part (e)

DIBAL-H is also a reducing agent that reduces esters to aldehyde by donation of hydride ion (H^-).

Detailed answer for part (f)

DIBAL-H is also a reducing agent that reduces esters to aldehyde by donation of hydride ion (H^-). The hydride ion (H^-) attacks the carbonyl carbon of the ester group and oxygen acts as a leaving group to finally form a open chain containing an aldehyde and alcoholic group as shown in the image: