Organic Chemistry-Package(Custom)
4th Edition
ISBN: 9781259141089
Author: SMITH
Publisher: MCG
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Chapter 24, Problem 24.7P
Interpretation Introduction
(a)
Interpretation: The product that is formed in the given crossed aldol reaction is to be drawn.
Concept introduction: The crossed aldol reaction takes place between the two different carbonyl compounds that is between two different
Interpretation Introduction
(b)
Interpretation: The product that is formed in the given crossed aldol reaction is to be drawn.
Concept introduction: The crossed aldol reaction takes place between the two different carbonyl compounds that is between two different aldehydes or two different ketones or one aldehyde and one ketone. The crossed aldol reaction takes place only if the carbonyl compound contains an acidic
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1. The following conversion includes chemistry we have covered very recently, some
chemistry from last term, and chemistry from the first chapter of this unit. Provide curly
arrows and an explanation for this mechanism. Use the reagents in the order given. You
do not need any other reagents.
1. NaOEt
OEt
2.
COOEt
COOEt
Step 1
Step 2
Step 3
COOEt
COOEt
COOH
Step 6
OH
Step 4
Step 7
(racemic)
cyclizes under
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OTS
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ОН
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Frontalin
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Shown above are the steps in one of the several published syntheses of Frontalin, a pheromone of the western pine beetle. From the choices provided, show
the reagents and conditions by which step 3 of this synthesis might be accomplished.
List the reagent(s) in order that will accomplish this transformation. No more than 4 steps are required. List your answer as a single letter (single-step
transformation) or a series of letters (multi-step transformation) with no commas separating them.
For example, "ab" corresponds to:
1. Eto Na+
2. NaOH, H₂O
NOTE: The order in which you list your letters matters!
Reagents:
a. Eto Na*
g. NaCN
b. NaOH, H₂O
h. SOCI₂
c. H3O+, heat
i. (CH3)2CuLi, ether, -78°C
d. LiAlH4
j. H₂O
e. p-TsCI, pyridine
k. RCO3H
f.
Br
I. H3O+
1,024
K
←
nationa
Login - Paymentivet
MapQue
Draw the major product of this reaction. Ignore inorganic
byproducts and the carboxylic acid side product.
N
1. excess LiAlH4
2. H₂O
✓
W
a
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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