EBK ORGANIC CHEMISTRY-STUD.SOLNS.MAN+SG
EBK ORGANIC CHEMISTRY-STUD.SOLNS.MAN+SG
4th Edition
ISBN: 9781119659525
Author: Klein
Publisher: WILEY CONS
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Chapter 25, Problem 89IP
Interpretation Introduction

Interpretation:

Alkyl halide required for preparation of tyrosine via amidomalonate synthesis and the polymeric material formed from the alkyl halide need to be identified.

Concept introduction:

Amidomalonate synthesis is a process in which a halide is converted to a aminoacid with two new carbon atoms (comes from amidomalonate).  By use of this method a new alkyl groups can be introduced.  A general scheme of this synthesis is shown below,

EBK ORGANIC CHEMISTRY-STUD.SOLNS.MAN+SG, Chapter 25, Problem 89IP

Steps involved in amidomalonater synthesis are,

  • Deprotonation of α carbon in amidomalonate
  • Alkylation of enolate
  • Hydrolysis of ester using aqueous acid
  • Decarboxylation at high temperature

Polymerization can occur when an nucleophilic center and an electrophilic center is present in the compound.  These centers if present in the same compound a polymer can be formed.

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#1. Retro-Electrochemical Reaction: A ring has been made, but the light is causing the molecule to un- cyclize. Undo the ring into all possible molecules. (2pts, no partial credit) hv
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I have a question about this problem involving mechanisms and drawing curved arrows for acids and bases. I know we need to identify the nucleophile and electrophile, but are there different types of reactions? For instance, what about Grignard reagents and other types that I might not be familiar with? Can you help me with this? I want to identify the names of the mechanisms for problems 1-14, such as Gilman reagents and others. Are they all the same? Also, could you rewrite it so I can better understand? The handwriting is pretty cluttered. Additionally, I need to label the nucleophile and electrophile, but my main concern is whether those reactions differ, like the "Brønsted-Lowry acid-base mechanism, Lewis acid-base mechanism, acid-catalyzed mechanisms, acid-catalyzed reactions, base-catalyzed reactions, nucleophilic substitution mechanisms (SN1 and SN2), elimination reactions (E1 and E2), organometallic mechanisms, and so forth."

Chapter 25 Solutions

EBK ORGANIC CHEMISTRY-STUD.SOLNS.MAN+SG

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