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Question 4. In the laboratory, reductions of carbonyl and carboxyl compounds are often carried out using reducing reagents, such as sodium borohydride (NaBH4) and lithium aluminum hydride (LiAlH4). While LiAlH4 can reduce aldehydes, ketones, and esters to the corresponding alcohols, NaBH4 cannot reduce esters. OH R `R'(H) alcohol no reaction 1) H Na+ H-B--H H 2) acidic 1) workup (H3O+) H Na* H-B™-H H 2) acidic workup (H3O+) R 'R'(H) aldehyde or ketone 1) NaBH4 2) acidic workup (H3O+) R OR' ester ملل 1) OEt H Li+ H-AI-H H 2) acidic 1) workup (H3O+) H Li+ H-AIH H 2) acidic workup (H3O+) OH 1) LIAIH4 2) acidic workup (H30+) R R'(H) a) Draw the products of reduction of the ß-ketoester shown below by NaBH4 and by LiAlH4. alcohol R OH + R'OH 1° alcohol b) Provide a rationale for why esters show decreased reactivity toward reduction by NaBH4, compared to aldehydes and ketones. c) Provide a rationale for the increased reactivity of LiAlH4 over NaBH4 that allows for the reduction of an ester. d) Explain why the reduction of esters by LiAlH4 proceeds to primary alcohol without stopping at the aldehyde.

Question 4. In the laboratory, reductions of carbonyl and carboxyl compounds are often carried out using reducing reagents, such as sodium borohydride (NaBH4) and lithium aluminum hydride (LiAlH4). While LiAlH4 can reduce aldehydes, ketones, and esters to the corresponding alcohols, NaBH4 cannot reduce esters. OH R `R'(H) alcohol no reaction 1) H Na+ H-B--H H 2) acidic 1) workup (H3O+) H Na* H-B™-H H 2) acidic workup (H3O+) R 'R'(H) aldehyde or ketone 1) NaBH4 2) acidic workup (H3O+) R OR' ester ملل 1) OEt H Li+ H-AI-H H 2) acidic 1) workup (H3O+) H Li+ H-AIH H 2) acidic workup (H3O+) OH 1) LIAIH4 2) acidic workup (H30+) R R'(H) a) Draw the products of reduction of the ß-ketoester shown below by NaBH4 and by LiAlH4. alcohol R OH + R'OH 1° alcohol b) Provide a rationale for why esters show decreased reactivity toward reduction by NaBH4, compared to aldehydes and ketones. c) Provide a rationale for the increased reactivity of LiAlH4 over NaBH4 that allows for the reduction of an ester. d) Explain why the reduction of esters by LiAlH4 proceeds to primary alcohol without stopping at the aldehyde.

Chemistry
Chemistry
10th Edition
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
Section: Chapter Questions
Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
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Question 4. In the laboratory, reductions of carbonyl and carboxyl compounds are often carried out using reducing reagents, such as sodium borohydride (NaBH4) and lithium aluminum hydride (LiAlH4). While LiAlH4 can reduce aldehydes, ketones, and esters to the corresponding alcohols, NaBH4 cannot reduce esters. OH R `R'(H) alcohol no reaction 1) H Na+ H-B--H H 2) acidic 1) workup (H3O+) H Na* H-B™-H H 2) acidic workup (H3O+) R 'R'(H) aldehyde or ketone 1) NaBH4 2) acidic workup (H3O+) R OR' ester ملل 1) OEt H Li+ H-AI-H H 2) acidic 1) workup (H3O+) H Li+ H-AIH H 2) acidic workup (H3O+) OH 1) LIAIH4 2) acidic workup (H30+) R R'(H) a) Draw the products of reduction of the ß-ketoester shown below by NaBH4 and by LiAlH4. alcohol R OH + R'OH 1° alcohol b) Provide a rationale for why esters show decreased reactivity toward reduction by NaBH4, compared to aldehydes and ketones. c) Provide a rationale for the increased reactivity of LiAlH4 over NaBH4 that allows for the reduction of an ester. d) Explain why the reduction of esters by LiAlH4 proceeds to primary alcohol without stopping at the aldehyde.
Transcribed Image Text:Question 4. In the laboratory, reductions of carbonyl and carboxyl compounds are often carried out using reducing reagents, such as sodium borohydride (NaBH4) and lithium aluminum hydride (LiAlH4). While LiAlH4 can reduce aldehydes, ketones, and esters to the corresponding alcohols, NaBH4 cannot reduce esters. OH R `R'(H) alcohol no reaction 1) H Na+ H-B--H H 2) acidic 1) workup (H3O+) H Na* H-B™-H H 2) acidic workup (H3O+) R 'R'(H) aldehyde or ketone 1) NaBH4 2) acidic workup (H3O+) R OR' ester ملل 1) OEt H Li+ H-AI-H H 2) acidic 1) workup (H3O+) H Li+ H-AIH H 2) acidic workup (H3O+) OH 1) LIAIH4 2) acidic workup (H30+) R R'(H) a) Draw the products of reduction of the ß-ketoester shown below by NaBH4 and by LiAlH4. alcohol R OH + R'OH 1° alcohol b) Provide a rationale for why esters show decreased reactivity toward reduction by NaBH4, compared to aldehydes and ketones. c) Provide a rationale for the increased reactivity of LiAlH4 over NaBH4 that allows for the reduction of an ester. d) Explain why the reduction of esters by LiAlH4 proceeds to primary alcohol without stopping at the aldehyde.
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