Organic Chemistry
11th Edition
ISBN: 9781118133576
Author: T. W. Graham Solomons, Craig Fryhle
Publisher: Wiley, John & Sons, Incorporated
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Chapter 20, Problem 12PP
Interpretation Introduction
Interpretation:
The compound,
Concept introduction:
Benzene and substituted benzene undergo electrophilic substitution reactions in the presence of an electrophile.
Aniline and substituted aniline react with nitrous acid at low temperature to form benzene diazonium salts.
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Practice Problem 19.54
Z Your answer is partially correct. Try again.
Predict the major product(s) (A - K) from the treatment of acetone with the following compounds (a-c):
NH2
HO
Eto
OEt
A:
B:
C:
D:
E:
F:
OH
OH
но
CN
G:
H:
I:
J:
(a) [H*], excess EtOH, (-H20)
Major Product(s):
(ь) NaBH4, Meон
B
Major Product(s):
(c) LAH followed by H20
Major Product(s):
SHOW HINT
(b) Propose a synthesis of (2,2-dimethylpropyl)benzene from benzene.
Gamma(y)-amino butyric acid (GABA) is a neurotransmitter (a chemical that is used to send signals from one neuron to another) of the
mammalian central nervous system. In order to understand how GABA works, conformationally restricted analogues, such as
compound 1, have been made. During a synthesis of compound 1, compound 2 was subjected to allylic bromination using NBS and a
radical initiator (AIBN) instead of light (Aust. J. Chem. 1981, 34, 2231-2236).
H₂N.
CH3
GABA
CO₂H
CH3
dddd
CH3
H₂N
Modify the structures given below to draw all eight possible allylic bromides that can be formed when compound 2 undergoes allylic
bromination, considering all possible regiochemical and stereochemical outcomes. You can use the single bond tool to add/remove pi
bonds.
CH3
CO₂H
CH3
solddd
CH3
CH3
2
CH₂
CO₂Et
Chapter 20 Solutions
Organic Chemistry
Ch. 20 - Prob. 1PPCh. 20 - Prob. 2PPCh. 20 - Prob. 3PPCh. 20 - PRACTICE PROBLEM 20.5 Outline a preparation of...Ch. 20 - Prob. 5PPCh. 20 - Prob. 6PPCh. 20 - Prob. 7PPCh. 20 - Prob. 8PPCh. 20 - Prob. 9PPCh. 20 - Practice Problem 20.11 In the preceding examples...
Ch. 20 - Prob. 11PPCh. 20 - Prob. 12PPCh. 20 - Practice Problem 20.14
Outline a synthesis of...Ch. 20 - Prob. 14PPCh. 20 - Prob. 15PPCh. 20 - PRACTICE PROBLEM
20.16
An amine A has the...Ch. 20 - PRACTICE PROBLEM Sulfonamides of primary amines...Ch. 20 - PRACTICE PROBLEM
20.18 (a) Starting with aniline...Ch. 20 - Prob. 19PCh. 20 - 20.20 Give common or systematic names for each of...Ch. 20 - Which is the most basic nitrogen in each compound?...Ch. 20 - Prob. 22PCh. 20 - Prob. 23PCh. 20 - Show how you might synthesize each of the...Ch. 20 - Prob. 25PCh. 20 - 20.26 Provide the major organic product from each...Ch. 20 - Prob. 27PCh. 20 - Prob. 28PCh. 20 - Prob. 29PCh. 20 - Prob. 30PCh. 20 - Prob. 31PCh. 20 - Write equations for simple chemical rests or state...Ch. 20 - Prob. 33PCh. 20 - 20.34 Using reactions that we have studied in this...Ch. 20 - 20.35 Provide a detailed mechanism for each of the...Ch. 20 - Prob. 36PCh. 20 - Prob. 37PCh. 20 - Prob. 38PCh. 20 - Prob. 39PCh. 20 - 20.40 Give structures for compounds R-W:
Ch. 20 - Prob. 41PCh. 20 - Prob. 42PCh. 20 - Diethylpropion (shown here) is a compound used in...Ch. 20 - Prob. 44PCh. 20 - 20.45 Compound W is soluble in dilute aqueous HCI...Ch. 20 - 20.46 Propose structures for compounds X, Y, and...Ch. 20 - Compound A(C10H15N) is soluble in dilute HCI. The...Ch. 20 - Prob. 48PCh. 20 - Prob. 49PCh. 20 - 20.52 When phenyl isochiocyanatc, , is reduced...Ch. 20 - Prob. 51PCh. 20 - 20.54 Propose a mechanism that can explain the...Ch. 20 - When acetone is treated with anhydrous ammonia in...Ch. 20 - Prob. 54PCh. 20 - Which of the following would be soluble in dilute...Ch. 20 - Which would yield propylamine? (d) Two of the...Ch. 20 - Select the reagent from the list below that could...Ch. 20 - Prob. 4QCh. 20 - 20.5 Select the stronger base from each pair (in...
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