Organic Chemistry-Package(Custom)
4th Edition
ISBN: 9781259141089
Author: SMITH
Publisher: MCG
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Chapter 24, Problem 24.33P
Interpretation Introduction
Interpretation: The structure of X is to be predicted.
Concept introduction: When only carbonyl component has an alpha hydrogen atom, then a cross aldol reaction will occur. There will be formation of only one product. The yield of single cross aldol condensation reaction is enhanced if the electrophilic carbonyl compound is relatively unhindered.
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2
H3C
H3C
H
C→XT
OH
H3C
The aldol reaction is a carbonyl condensation reaction between two carbonyl partners and involves a combination of nucleophilic addition
and a-substitution steps. One partner is converted into an enolate ion nucleophile and adds to the electrophilic carbonyl group of the
second partner. In the classic aldol reaction, the carbonyl partners are aldehydes or ketones, although aldehydes are more reactive. The
product is a ß-hydroxy carbonyl compound.
base
:0:
OH
H
H
Under reaction conditions slightly more vigorous than those employed for the aldol reaction, the ß-hydroxyl group is eliminated in an E1cB
dehydration to give an a,ß-unsaturated carbonyl compound.
Draw curved arrows to show the movement of electrons in this step of the mechanism.
Arrow-pushing Instruct ns
H3C
heat
OH
H3C
:0:
H
+ H₂O
H
20:24
:
●●●
E) 03
12. Fill in the box with the major organic product of the first step of the reaction shown?
The first step of the reaction shown is an exhaustive methylation and is one of the
SN2, SN1, E2, or E1 reactions.
Another piece of information about this full reaction, the second step proceeds via an
E2 mechanism.
xs CH₂l
13. What is the name of the reaction in the previous question?
A) Swern Oxidation
Hofmann Elimination
ABCD
Ag₂O, A
Cope Elimination
Williamson Ether Synthesis
Send a chat
O
Ketones and aldehydes react with sodium acetylide (the sodium salt of acetylene) to give alcohols, as shown in the following example:
R1
ОН
1. НС—с: Na*
R2
R1
R2
2. Нзо"
HC
Draw the structure of the major reaction product when the following compound reacts with sodium acetylide, assuming that the reaction takes
preferentially from the Si face of the carbonyl group.
• Use the wedge/hash bond tools to indicate stereochemistry where it exists.
• You do not have to explicitly draw H atoms.
• If a group is achiral, do not use wedged or hashed bonds on it.
CH3
CH
Chapter 24 Solutions
Organic Chemistry-Package(Custom)
Ch. 24 - Prob. 24.1PCh. 24 - Prob. 24.2PCh. 24 - Problem 24.3
What unsaturated carbonyl compound is...Ch. 24 - Acid-catalyzed dehydration of hydroxy carbonyl...Ch. 24 - Prob. 24.5PCh. 24 - Prob. 24.6PCh. 24 - Prob. 24.7PCh. 24 - Problem 24.8
Draw the products formed in the...Ch. 24 - Prob. 24.9PCh. 24 - Prob. 24.10P
Ch. 24 - Prob. 24.11PCh. 24 - Prob. 24.12PCh. 24 - Prob. 24.13PCh. 24 - Prob. 24.14PCh. 24 - Problem 24.16
What ester is formed when each...Ch. 24 - What crossed Claisen product is formed from each...Ch. 24 - Prob. 24.17PCh. 24 -
Draw the products of each reaction.
a. b.
Ch. 24 - Problem 24.20
Two steps in a synthesis of the...Ch. 24 - Prob. 24.20PCh. 24 - Problem 24.22
Which of the following compounds can...Ch. 24 - What product is formed when each pair of compounds...Ch. 24 - Problem 24.24
What starting materials are needed...Ch. 24 - Problem 24.25
Draw the products when each pair of...Ch. 24 - Problem 24.27
What starting materials are needed...Ch. 24 - Prob. 24.26PCh. 24 - 24.29 What steps are needed to convert A to B?
Ch. 24 - Prob. 24.28PCh. 24 - Prob. 24.29PCh. 24 - 24.31 Draw the product formed in each directed...Ch. 24 - Prob. 24.31PCh. 24 - What starting materials are needed to synthesize...Ch. 24 - Prob. 24.33PCh. 24 - Prob. 24.34PCh. 24 - Prob. 24.35PCh. 24 - 24.36 Identify the structures of C and D in the...Ch. 24 - Prob. 24.37PCh. 24 - Prob. 24.38PCh. 24 - Prob. 24.39PCh. 24 - Draw the product formed from a Claisen reaction...Ch. 24 - Prob. 24.41PCh. 24 - 24.41 Even though B contains three ester groups, a...Ch. 24 - Prob. 24.43PCh. 24 - What starting materials are needed to prepare each...Ch. 24 - 24.44 Vetivone is isolated from vetiver, a...Ch. 24 - Draw the product of each Robinson annulation from...Ch. 24 - Prob. 24.47PCh. 24 - Draw the organic products formed when butanal...Ch. 24 - 24.47 Draw the organic products formed in each...Ch. 24 - 24.48 Fill in the lettered reagents needed for...Ch. 24 - Prob. 24.51PCh. 24 - Prob. 24.52PCh. 24 - Prob. 24.53PCh. 24 - Draw a stepwise mechanism for the following...Ch. 24 - Prob. 24.55PCh. 24 - Prob. 24.56PCh. 24 - Prob. 24.57PCh. 24 - Prob. 24.58PCh. 24 - Prob. 24.59PCh. 24 - Prob. 24.60PCh. 24 - Prob. 24.61PCh. 24 - Prob. 24.62PCh. 24 - Devise a synthesis of each compound from...Ch. 24 - Prob. 24.64PCh. 24 - Prob. 24.65PCh. 24 - Prob. 24.66PCh. 24 - 24.65 Answer the following questions about...Ch. 24 - Prob. 24.68PCh. 24 - Prob. 24.69PCh. 24 - Prob. 24.70PCh. 24 - Prob. 24.71PCh. 24 - 24.70 Draw a stepwise mechanism for the following...Ch. 24 - Prob. 24.73PCh. 24 - Prob. 24.74PCh. 24 - Prob. 24.75P
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