Organic Chemistry
Organic Chemistry
12th Edition
ISBN: 9781118875766
Author: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder
Publisher: WILEY
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Chapter 19, Problem 10PP
Interpretation Introduction

Interpretation:

The synthesis of each of the given product from butanal is to be shown.

Concept Introduction:

In aldol addition and aldol condensation, a CC bond formation takes place.

Aldol condensation occurs in a protic solvent in the presence of a base.

Inacid catalysis, the direct dehydration of the aldol intermediate leads to the formation of the α,β unsaturated product.

LiAlH4 reduces the carbonyl groups of aldehyde and ketone, whereas NaBH4 reduces the carbon-carbon double bond.

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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
19.54 Predict the major product(s) from the treatment of acetone with the following: (d) [H], (CH3)2NH, (-H2O) (e) [H], NH2NH2, (-H2O) (f) [H], NH2OH, (-H2O) (g) NaBH4, MeOH (h) RCO3H (i) HCN, KCN (j) EtMgBr followed by H₂O (k) (C6H5)3P=CHCH2CH3 (1) LIAIH, followed by H2O
Provide reagents

Chapter 19 Solutions

Organic Chemistry

Ch. 19 - Practice Problem 19.11 Outlined below is a...Ch. 19 - Prob. 12PPCh. 19 - Prob. 13PPCh. 19 - Prob. 14PPCh. 19 - Practice Problem 19.15 Starting with ketones and...Ch. 19 - Practice Problem 19.16 Assuming that dehydration...Ch. 19 - Practice Problem 19.17 What starting compound...Ch. 19 - Practice Problem 19.18 What experimental...Ch. 19 - Prob. 19PPCh. 19 - Practice Problem 19.20 When acrolein (propenal)...Ch. 19 - Prob. 21PPCh. 19 - PRACTICE PROBLEM 19.22 Qutline reasonable...Ch. 19 - Prob. 23PCh. 19 - Show all steps in the following syntheses. You may...Ch. 19 - Prob. 25PCh. 19 - Prob. 26PCh. 19 - Prob. 27PCh. 19 - 19.28 Show how the diketone at the right could be...Ch. 19 - Prob. 29PCh. 19 - 19.30 Write a detailed mechanism for the following...Ch. 19 - Prob. 31PCh. 19 - Prob. 32PCh. 19 - 19.33 Predict the products from each of the...Ch. 19 - Prob. 34PCh. 19 - Show how each of the following transformations...Ch. 19 - Prob. 36PCh. 19 - What reagents would you use to bring about each...Ch. 19 - Prob. 38PCh. 19 - Prob. 39PCh. 19 - 19.40 When the aldol reaction of acetaldehyde is...Ch. 19 - Prob. 41PCh. 19 - Prob. 42PCh. 19 - 19.43 The following reaction illustrates the...Ch. 19 - What is the structure of the cyclic compound that...Ch. 19 - Prob. 45PCh. 19 - Prob. 46PCh. 19 - Prob. 47PCh. 19 - Predict the products from the following reactions....Ch. 19 - Prob. 49PCh. 19 - Prob. 50PCh. 19 - Prob. 51PCh. 19 - Prob. 52PCh. 19 - Prob. 53PCh. 19 - The Perkin condensation is an aldol-type...Ch. 19 - 19.55 (a) Infrared spectroscopy provides an easy...Ch. 19 - Allowing acetone to react with 2 molar equivalents...Ch. 19 - (+) Fenchone is a terpenoid that can be isolated...Ch. 19 - Prob. 58PCh. 19 - Prob. 59PCh. 19 - 19.60 Develop a synthesis for the following...Ch. 19 - 19.61 Provide a mechanism for each of the...Ch. 19 - 19.62 (a) Deduce the structure of product A,...Ch. 19 - Prob. 63PCh. 19 - Prob. 1LGP
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