ORGANIC CHEMISTRY-STUDY GDE./SOL.MAN.
6th Edition
ISBN: 9780072397475
Author: SMITH
Publisher: MCG
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Chapter 22.6, Problem 19P
Interpretation Introduction
Interpretation: The two different crossed Claisen reactions that form avobenzone are to be shown.
Concept Introduction: In crossed claisen condensation reaction, the base abstracts the acidic proton from
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4. C6H100
5
I peak
3
2
PPM
Integration values: 1.79ppm (2), 4.43ppm (1.33)
Ipeak
None
3. Consider the compounds below and determine if they are aromatic, antiaromatic, or
non-aromatic. In case of aromatic or anti-aromatic, please indicate number of I
electrons in the respective systems. (Hint: 1. Not all lone pair electrons were explicitly
drawn and you should be able to tell that the bonding electrons and lone pair electrons
should reside in which hybridized atomic orbital 2. You should consider ring strain-
flexibility and steric repulsion that facilitates adoption of aromaticity or avoidance of anti-
aromaticity)
H H
N
N:
NH2
N
Aromaticity
(Circle)
Aromatic Aromatic Aromatic Aromatic Aromatic
Antiaromatic Antiaromatic Antiaromatic Antiaromatic Antiaromatic
nonaromatic nonaromatic nonaromatic nonaromatic nonaromatic
aromatic TT
electrons
Me
H
Me
Aromaticity
(Circle)
Aromatic Aromatic Aromatic
Aromatic Aromatic
Antiaromatic Antiaromatic Antiaromatic Antiaromatic Antiaromatic
nonaromatic nonaromatic nonaromatic nonaromatic nonaromatic
aromatic πT
electrons
H
HH…
Chapter 22 Solutions
ORGANIC CHEMISTRY-STUDY GDE./SOL.MAN.
Ch. 22.1 - Prob. 1PCh. 22.1 - Prob. 2PCh. 22.1 - Problem 24.3
What unsaturated carbonyl compound is...Ch. 22.1 - Prob. 4PCh. 22.1 - Prob. 5PCh. 22.2 - Prob. 6PCh. 22.2 - Problem 24.7
Draw the products formed in each...Ch. 22.4 - Prob. 15PCh. 22.4 - Prob. 16PCh. 22.5 - Problem 24.16
What ester is formed when each...
Ch. 22.6 - Prob. 18PCh. 22.6 - Prob. 19PCh. 22.6 -
Draw the products of each reaction.
a. b.
Ch. 22.6 - Problem 24.20
Two steps in a synthesis of the...Ch. 22.7 - Prob. 22PCh. 22.8 - Problem 24.22
Which of the following compounds can...Ch. 22.8 - Prob. 24PCh. 22.8 - Problem 24.24
What starting materials are needed...Ch. 22 - Prob. 29PCh. 22 - 24.29 What steps are needed to convert A to B?
Ch. 22 - Prob. 31PCh. 22 - 24.31 Draw the product formed in each directed...Ch. 22 - Prob. 33PCh. 22 - 24.33 What starting materials are needed to...Ch. 22 - Prob. 35PCh. 22 - Prob. 36PCh. 22 - 24.36 Identify the structures of C and D in the...Ch. 22 - Prob. 38PCh. 22 - Prob. 39PCh. 22 - 24.39 Draw the product formed from a Claisen...Ch. 22 - Prob. 41PCh. 22 - 24.41 Even though B contains three ester groups, a...Ch. 22 - Prob. 43PCh. 22 - Prob. 44PCh. 22 - 24.44 Vetivone is isolated from vetiver, a...Ch. 22 - Draw the product of each Robinson annulation from...Ch. 22 - Prob. 50PCh. 22 - Prob. 51PCh. 22 - 24.52 Draw a stepwise mechanism for the following...Ch. 22 - Prob. 53PCh. 22 - Prob. 54PCh. 22 - Prob. 55PCh. 22 - Prob. 56PCh. 22 - Prob. 57PCh. 22 - Prob. 58PCh. 22 - Prob. 59PCh. 22 - 24.62 Devise a synthesis of each compound from ,...Ch. 22 - Prob. 63P
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