Homework Help is Here – Start Your Trial Now!
Science
Chemistry
Lithium borohydride (LiBH4) is a useful reducing agent, as it is more selective than LiAlH4 but less selective than NaBH4. Specifically, LiBH4 will reduce esters, but it will not reduce amides. This selectivity is frequently employed by synthetic organic chemists. For example, during a synthesis of (-)-croalbinecine, a natural product with cytotoxic properties, compound 1 was converted to compound 3, as shown below (J. Org. Chem. 2000, 65, 9249-9251). Draw the structures of 2 and 3. CO₂Et но. Ph OCH 1) Excess LiBH4 2) H₂O 2 1) Excess NaH, excess PhCH₂Br, DMF 2) H₂, Lindlar's catalyst 3

Lithium borohydride (LiBH4) is a useful reducing agent, as it is more selective than LiAlH4 but less selective than NaBH4. Specifically, LiBH4 will reduce esters, but it will not reduce amides. This selectivity is frequently employed by synthetic organic chemists. For example, during a synthesis of (-)-croalbinecine, a natural product with cytotoxic properties, compound 1 was converted to compound 3, as shown below (J. Org. Chem. 2000, 65, 9249-9251). Draw the structures of 2 and 3. CO₂Et но. Ph OCH 1) Excess LiBH4 2) H₂O 2 1) Excess NaH, excess PhCH₂Br, DMF 2) H₂, Lindlar's catalyst 3

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...
See similar textbooks
icon
Related questions
Question
100%
Lithium borohydride (LiBH4) is a useful reducing agent, as it is more selective than LIAIH4 but less selective than NaBH4. Specifically, LiBH4 will reduce esters, but it will not reduce amides. This selectivity is frequently employed by synthetic organic chemists. For example, during a synthesis of (-)-croalbinecine, a natural product with cytotoxic properties, compound 1 was converted to compound 3, as shown below (J. Org. Chem. 2000, 65, 9249-9251). Draw the structures of 2 and 3. CO₂Et но- 1 -N Ph 1) Excess LiBH4 2) H₂O OCH 3 2 1) Excess NaH, excess PhCH₂Br, DMF 2) H₂, Lindlar's catalyst 3
Transcribed Image Text:Lithium borohydride (LiBH4) is a useful reducing agent, as it is more selective than LIAIH4 but less selective than NaBH4. Specifically, LiBH4 will reduce esters, but it will not reduce amides. This selectivity is frequently employed by synthetic organic chemists. For example, during a synthesis of (-)-croalbinecine, a natural product with cytotoxic properties, compound 1 was converted to compound 3, as shown below (J. Org. Chem. 2000, 65, 9249-9251). Draw the structures of 2 and 3. CO₂Et но- 1 -N Ph 1) Excess LiBH4 2) H₂O OCH 3 2 1) Excess NaH, excess PhCH₂Br, DMF 2) H₂, Lindlar's catalyst 3
Expert Solution
trending now

Trending now

This is a popular solution!

steps

Step by step

Solved in 3 steps with 1 images

SEE SOLUTIONCheck out a sample Q&A here
Blurred answer
Knowledge Booster
Aldehydes and Ketones
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.
Similar questions
Recommended textbooks for you
Chemistry
Chemistry
Chemistry
ISBN:
9781305957404
Author:
Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:
Cengage Learning
Chemistry
Chemistry
Chemistry
ISBN:
9781259911156
Author:
Raymond Chang Dr., Jason Overby Professor
Publisher:
McGraw-Hill Education
Principles of Instrumental Analysis
Principles of Instrumental Analysis
Chemistry
ISBN:
9781305577213
Author:
Douglas A. Skoog, F. James Holler, Stanley R. Crouch
Publisher:
Cengage Learning
Organic Chemistry
Organic Chemistry
Chemistry
ISBN:
9780078021558
Author:
Janice Gorzynski Smith Dr.
Publisher:
McGraw-Hill Education
Chemistry: Principles and Reactions
Chemistry: Principles and Reactions
Chemistry
ISBN:
9781305079373
Author:
William L. Masterton, Cecile N. Hurley
Publisher:
Cengage Learning
Elementary Principles of Chemical Processes, Bind…
Elementary Principles of Chemical Processes, Bind…
Chemistry
ISBN:
9781118431221
Author:
Richard M. Felder, Ronald W. Rousseau, Lisa G. Bullard
Publisher:
WILEY
SEE MORE TEXTBOOKS