Organic Chemistry
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 46P

Propose structures for compounds X, Y, and Z:

X ( C 7 H 7 B r ) N a C N Y ( C 8 H 7 N ) L i A l H 4 Z ( C 8 H 11 N )

The 1 H NMR spectrum of X gives two signals, a multiplet at δ 7.3 (5H) and a singlet at δ 4.25 (2H); the 680-840 c m 1 region of the IR spectrum of X shows peaks at 690 and 770 c m 1 . The 1 H NMR spectrum of Y is similar to that of X: multiplet at δ 7.3 (5H), singlet at δ 3.7(2H). The 1 H NMR spectrum of Z is shown in Fig. 20.7.

Chapter 20, Problem 46P, 20.46	Propose structures for compounds X, Y, and Z:

	The  NMR spectrum of X gives two signals, a

FIGURE 20.7 The 1 H NMR spectrum of compound Z. Problem 20.46. Expansion of the signals is shown in the offset plot.

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Chapter 20 Solutions

Organic Chemistry

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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