ORGANIC CHEMISTRY (LL) W/WILEYPLUS NEXT
12th Edition
ISBN: 9781119664635
Author: Solomons
Publisher: WILEY
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Chapter 20, Problem 6PP
Interpretation Introduction
Interpretation:
The preparation of each amine through reductive amination is to be shown.
Concept Introduction:
The conversion of
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Show how to synthesize the following amines from the indicated starting materials.(a) N-cyclopentylaniline from aniline (b) N-ethylpyrrolidine from pyrrolidine
Show how to synthesize the following amines from the indicated starting materials byreductive amination.(a) benzylmethylamine from benzaldehyde
Show how to prepare the following aromatic amines by aromatic nitration, followed by reduction. You may use benzene andtoluene as your aromatic starting materials. (c) m-bromoaniline (d) m-aminobenzoic acid
Chapter 20 Solutions
ORGANIC CHEMISTRY (LL) W/WILEYPLUS NEXT
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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- Arrange the members of each group in order of decreasing basicity: (a) Ammonia, aniline, methylamine (b) Acetanilide, aniline, N-methylaniline (c) 2,4-Dichloroaniline, 2,4-dimethylaniline, 2,4-dinitroaniline (d) 3,4-Dichloroaniline, 4-chloro-2-nitroaniline, 4-chloro-3-nitroaniline (e) Dimethylamine, diphenylamine, N-methylanilinearrow_forwardShow how to synthesize the following amines from the indicated starting materials.(a) N-cyclopentylaniline from anilinearrow_forwardShow how to synthesize the following amines from the indicated starting materials byacylation–reduction.(a) N-butylpiperidine from piperidinearrow_forward
- The two most general amine syntheses are the reductive amination of carbonyl compounds and the reduction of amides.Show how these techniques can be used to accomplish the following syntheses.(a) benzoic acid S benzylamine (b) benzaldehyde S benzylamine(c) pyrrolidine S N@ethylpyrrolidine (d) cyclohexanone S N@cyclohexylpyrrolidine(e) HOOC¬(CH2)3 ¬COOH S pentane@1,5@diamine (cadaverine)arrow_forwardShow how you would use appropriate acyl chlorides and amines to synthesize thefollowing amides.(a) N,N-dimethylacetamide (b) acetanilide (PhNHCOCH3)(c) cyclohexanecarboxamide (d)arrow_forwardPredict the products from the reactions of the following amines with sodium nitrite indilute HCl.(a) cyclohexanaminearrow_forward
- Draw a structural formula for each amine and amine derivative. (a) N,N-Dimethylaniline (b) Triethylamine (c) tert-Butylamine (d) 1,4-Benzenediamine (e) 4-Aminobutanoic acid (f) (R)-2-Butanamine (g) Benzylamine (h) trans-2-Aminocyclohexanol (i) 1-Phenyl-2-propanamine (amphetamine) (j) Lithium diisopropylamide (LDA) (k) Benzyltrimethylammonium hydroxide (Triton B)arrow_forwardGive the products expected when the following tertiary amines are treated with a peroxyacid and heated.(a) N,N-dimethylhexan-2-aminearrow_forwardGive the products expected when the following tertiary amines are treated with a peroxyacid and heated.cyclohexyldimethylaminearrow_forward
- Show how to prepare the following aromatic amines by aromatic nitration, followed by reduction. You may use benzene andtoluene as your aromatic starting materials. c) m-bromoanilinearrow_forwardShow how to synthesize the following amines from the indicated starting materials byreductive amination. ) N-cyclohexylaniline from cyclohexanonearrow_forward(D)The best route to synthesise aromatic primary amines is by reduction of the corresponding nitro compounds. Draw the reaction scheme for the preparation of p-toluidine.arrow_forward
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