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 16PP

PRACTICE PROBLEM

An amine A has the molecular formula C7H9N. Compound A reacts with benzenesulfonyl chloride in aqueous potassium hydroxide to give a clear solution; acidification of the solution gives a precipitate. When A is treated with NaNO2 and HCl at 0–5 °C, and then with 2-naphthol, an intensely colored compound is formed. Compound A gives a single strong IR absorption peak at 815 cm−1. What is the structure of A?

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b. CH3 H3C CH3 CH3 H3C an unexpected product, containing a single 9- membered ring the expected product, containing two fused rings H3C-I (H3C)2CuLi an enolate
b. H3C CH3 1. 2. H3O+ H3C MgBr H3C
Predict the major products of this reaction: excess H+ NaOH ? A Note that the first reactant is used in excess, that is, there is much more of the first reactant than the second. If there won't be any products, just check the box under the drawing area instead. Explanation Check Click and drag to start drawing a structure. © 2025 McGraw Hill LLC. All Rights Reserved. Terms of Use Priv

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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