1. An aldol reaction begins with addition of a catalytic amount of base to an aldehyde or ketone. Writethe first step (formation of an enolate) of the reaction when a catalytic amount of NaOH is added toacetaldehyde.BaseHHZH2. Continue the reaction in problem 1 showing reaction of the enolate with an unaffected molecule ofacetaldehyde forming an alkoxide. Subsequent reaction with water yields a B-hydroxyaldehyde.OH-=7HbaseHOHoнияHHटेHaloCThe overall reaction in problems 1 and 2 is an aldol addition reaction. Each step is reversible. Write themechanism for the reverse process converting the B-hydroxyaldehyde into two molecules of the originalaldehyde. This process is a retro-aldol reaction. Use pK, values to explain why the process is reversible.-OH-e7LHlobia.Write the mechanism for reaction of butanone with catalytic aqueous NaOH. (Show each step with areversible reaction arrow.)

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1. An aldol reaction begins with addition of a catalytic amount of base to an aldehyde or ketone. Write the first step (formation of an enolate) of the reaction when a catalytic amount of NaOH is added to acetaldehyde. 11 Bose

1. An aldol reaction begins with addition of a catalytic amount of base to an aldehyde or ketone. Write the first step (formation of an enolate) of the reaction when a catalytic amount of NaOH is added to acetaldehyde. 11 Bose

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter24: Catalytic Carbon-carbon Bond Formation

Section: Chapter Questions

Problem 24.9P

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Concept explainers

Reactions at the Alpha Carbon Atom

The position next to the ketone or aldehyde functional group is termed as alpha position and the reaction which occurs at alpha position is called alpha substitution reaction. In an alpha substitution reaction, the alpha proton atom is substituted by an electrophile by the formation of an enol intermediate or enolate ion intermediate. Most of the carbonyl compounds go through an alpha substitution reaction.

Question

1. An aldol reaction begins with addition of a catalytic amount of base to an aldehyde or ketone. Write
the first step (formation of an enolate) of the reaction when a catalytic amount of NaOH is added to
acetaldehyde.
Base
HH
Z
H
2. Continue the reaction in problem 1 showing reaction of the enolate with an unaffected molecule of
acetaldehyde forming an alkoxide. Subsequent reaction with water yields a B-hydroxyaldehyde.
OH
-=7
H
base
H
OH
o
ния
H
H
टे
H
alo
C
The overall reaction in problems 1 and 2 is an aldol addition reaction. Each step is reversible. Write the
mechanism for the reverse process converting the B-hydroxyaldehyde into two molecules of the original
aldehyde. This process is a retro-aldol reaction. Use pK, values to explain why the process is reversible.
-OH-
e
7L
Hlobia.
Write the mechanism for reaction of butanone with catalytic aqueous NaOH. (Show each step with a
reversible reaction arrow.)

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