How to synthesize serine by a simple variation of amidomalonate method using formaldehyde instead of an alkyl halide is to be shown. Concept introduction: The steps involved in the synthesis of leucine by acetamidomalonate method are i) Conversion of the diethyl acetamidomalonate to an enolate ion by treatment with a base ii) SN 2 alkylation with a primary alkyl halide iii) Hydrolysis of the amide protecting group and ester groups by warming the alkylated product with aqueous acids. The reaction can also be carried out using formaldehyde instead of an alkyl halide. To give: How to synthesize serine by a simple variation of amidomalonate method using formaldehyde instead of an alkyl halide.

Question

Want to see the full answer?

Answer 1

Question

Chapter 26.SE, Problem 39AP

Interpretation Introduction

Interpretation:

How to synthesize serine by a simple variation of amidomalonate method using formaldehyde instead of an alkyl halide is to be shown.

Concept introduction:

The steps involved in the synthesis of leucine by acetamidomalonate method are i) Conversion of the diethyl acetamidomalonate to an enolate ion by treatment with a base ii) SN² alkylation with a primary alkyl halide iii) Hydrolysis of the amide protecting group and ester groups by warming the alkylated product with aqueous acids.

The reaction can also be carried out using formaldehyde instead of an alkyl halide.

To give:

How to synthesize serine by a simple variation of amidomalonate method using formaldehyde instead of an alkyl halide.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

Students have asked these similar questions

Hi!! Please provide a solution that is handwritten. Ensure all figures, reaction mechanisms (with arrows and lone pairs please!!), and structures are clearly drawn to illustrate the synthesis of the product as per the standards of a third year organic chemistry course. ****the solution must include all steps, mechanisms, and intermediate structures as required. Please hand-draw the mechanisms and structures to support your explanation. Don’t give me AI-generated diagrams or text-based explanations, no wordy explanations on how to draw the structures I need help with the exact mechanism hand drawn by you!!! I am reposting this—ensure all parts of the question are straightforward and clear or please let another expert handle it thanks!!

. (11pts total) Consider the arrows pointing at three different carbon-carbon bonds in the molecule depicted below. Bond B 2°C. +2°C. < cleavage Bond A • CH3 + 26. t cleavage 2°C• +3°C• Bond C Cleavage CH3 ZC '2°C. 26. E Strongest 3°C. 2C. Gund Largest BDE weakest bond In that molecule a. (2pts) Which bond between A-C is weakest? Which is strongest? Place answers in appropriate boxes. Weakest C bond Produces A Weakest Bond Most Strongest Bond Stable radical Strongest Gund produces least stable radicals b. (4pts) Consider the relative stability of all cleavage products that form when bonds A, B, AND C are homolytically cleaved/broken. Hint: cleavage products of bonds A, B, and C are all carbon radicals. i. Which ONE cleavage product is the most stable? A condensed or bond line representation is fine. 人 8°C. formed in bound C cleavage ii. Which ONE cleavage product is the least stable? A condensed or bond line representation is fine. methyl radical •CH3 formed in bund A Cleavage