Organic Chemistry, 12e Study Guide/Student Solutions Manual
12th Edition
ISBN: 9781119077329
Author: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder
Publisher: WILEY
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Chapter 20, Problem 17PP
Interpretation Introduction
Interpretation:
The synthesis of N-methyl benzylamine from either methylamine or benzylamine by alkylation of a sulfonamide is to be shown.
Concept introduction:
Sulfonamide is a
The functional group acts as a nucleophile when used for alkylation reactions with electrophiles.
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Devise a synthesis of benzocaine, ethyl p-aminobenzoate (H2NC6H4CO2CH2CH3), from benzene, organic alcohols, and any needed organic or inorganic reagents. Benzocaine is the active ingredient in the topical anesthetic Orajel (Section 18.15C).
Show how to synthesize the following amines from the indicated starting materials byreductive amination.(a) benzylmethylamine from benzaldehyde
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
Chapter 20 Solutions
Organic Chemistry, 12e Study Guide/Student Solutions Manual
Ch. 20 - Prob. 1PPCh. 20 - Prob. 2PPCh. 20 - Practice Problem 20.3
Write a mechanism that...Ch. 20 - Prob. 4PPCh. 20 - PRACTICE PROBLEM 20.5 Outline a preparation of...Ch. 20 - Prob. 6PPCh. 20 - Prob. 7PPCh. 20 - Prob. 8PPCh. 20 - Prob. 9PPCh. 20 - Prob. 10PP
Ch. 20 - Practice Problem 20.11 In the preceding examples...Ch. 20 - Prob. 12PPCh. 20 - Prob. 13PPCh. 20 - Practice Problem 20.14
Outline a synthesis of...Ch. 20 - Prob. 15PPCh. 20 - Prob. 16PPCh. 20 - Prob. 17PPCh. 20 - Prob. 18PPCh. 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 - 20.28 What products would you expect to be formed...Ch. 20 - Prob. 29PCh. 20 - Prob. 30PCh. 20 - Prob. 31PCh. 20 - Write equations for simple chemical rests or state...Ch. 20 - Prob. 33PCh. 20 - Explain the following, including mention of key...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 - For each of the following, identify the product...Ch. 20 - 20.51 Develop a synthesis for the following...Ch. 20 - 20.52 When phenyl isochiocyanatc, , is reduced...Ch. 20 - Prob. 53PCh. 20 - 20.54 Propose a mechanism that can explain the...Ch. 20 - When acetone is treated with anhydrous ammonia in...Ch. 20 - Prob. 56P
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- Show how to synthesize the following amines from the indicated starting materials byacylation–reduction. b) N-benzylaniline from anilinearrow_forwardN-Methylbenzamide, an isomer of acetanilide, when allowed to react with HNO3/H2SO4 gives a different product from what is obtained from acetanilide. What is the structure of the mononitrated product? Why is it produced?arrow_forwardIbufenac, a para-disubstituted arene with the structure HO2CCH2C6H4CH2CH(CH3)2, is a much more potent analgesic than aspirin, but it was never sold commercially because it caused liver toxicity in some clinical trials. Devise a synthesis of ibufenac from benzene and organic halides having fewer than five carbons.arrow_forward
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