Organic Chemistry
Organic Chemistry
5th Edition
ISBN: 9780078021558
Author: Janice Gorzynski Smith Dr.
Publisher: McGraw-Hill Education
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Chapter 23, Problem 23.69P

Treatment of W with CH 3 Li , followed by CH 3 I , affords compound Y ( C 7 H 14 O ) as the major product. Y shows a strong absorption in its IR spectrum at 1713 cm 1 , and its 1 H NMR spectrum is given below. (a) Propose a structure f or Y. (b) Draw a stepwise mechanism f or the conversion of W to Y.

Chapter 23, Problem 23.69P, 23.69 	Treatment of W with , followed by , affords compound Y  as the 
	major product. Y shows a , example  1

Chapter 23, Problem 23.69P, 23.69 	Treatment of W with , followed by , affords compound Y  as the 
	major product. Y shows a , example  2

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Treatment of W with CH3Li, followed by CH3I, affords compound Y (C7H14O) as the major product. Y shows a strong absorption in its IR spectrum at 1713 cm−1, and its 1H NMR spectrum is given below, (a) Propose a structure for Y. (b) Draw a stepwise mechanism for the conversion of W to Y.
Identify products A and B from the given 1H NMR data. Treatment of CH2=CHCOCH3 with one equivalent of HCl forms compound A. A exhibits the following absorptions in its 1H NMR spectrum: 2.2 (singlet, 3H), 3.05 (triplet, 2 H), and 3.6 (triplet, 2 H) ppm. What is the structure of A?
Identify products A and B from the given 1H NMR data. Treatment of acetone [(CH3)2C=O] with dilute aqueous base forms B. Compound B exhibits four singlets in its 1H NMR spectrum at 1.3 (6 H), 2.2 (3 H), 2.5 (2 H), and 3.8 (1H) ppm. What is the structure of B?

Chapter 23 Solutions

Organic Chemistry

Ch. 23 - Problem 23.11 Draw the products of each...Ch. 23 - Problem 23.12 Draw the products of each reaction....Ch. 23 - Prob. 23.13PCh. 23 - Prob. 23.14PCh. 23 - Prob. 23.15PCh. 23 - Prob. 23.16PCh. 23 - Prob. 23.17PCh. 23 - Problem 23.18 How can pentan-2-one be converted...Ch. 23 - Problem 23.19 Identify A, B, and C, intermediates...Ch. 23 - Problem 23.20 Which of the following compounds...Ch. 23 - Problem 23.21 Draw the products of each...Ch. 23 - Prob. 23.22PCh. 23 - Prob. 23.23PCh. 23 - Prob. 23.24PCh. 23 - Prob. 23.25PCh. 23 - Prob. 23.26PCh. 23 - Prob. 23.27PCh. 23 - Prob. 23.28PCh. 23 - 23.29 Draw enol tautomer(s) for each compound....Ch. 23 - 22.30 The cis ketone A is isomerized to a trans...Ch. 23 - 23.31 Draw enol tautomer(s) for each compound. ...Ch. 23 - Prob. 23.32PCh. 23 - Prob. 23.33PCh. 23 - Prob. 23.34PCh. 23 - 23.35 Rank the labeled protons in each compound in...Ch. 23 - Prob. 23.36PCh. 23 - Prob. 23.37PCh. 23 - 23.38 Acyclovir is an effective antiviral agent...Ch. 23 - 23.39 Explain why forms two different alkylation...Ch. 23 - Prob. 23.40PCh. 23 - 23.41 Acid-catalyzed bromination of pentanone ...Ch. 23 - 23.42 Draw a stepwise mechanism for the following...Ch. 23 - Prob. 23.43PCh. 23 - Prob. 23.44PCh. 23 - 23.45 Devise a synthesis of valproic acid , a...Ch. 23 - 23.46 Synthesize each compound from diethyl...Ch. 23 - Prob. 23.47PCh. 23 - Prob. 23.48PCh. 23 - Prob. 23.49PCh. 23 - 23.50 Draw the organic products formed in each...Ch. 23 - 23.51 Draw the products formed (including...Ch. 23 - Prob. 23.52PCh. 23 - Prob. 23.53PCh. 23 - 23.54 Clopidogrel is the generic name for Plavix,...Ch. 23 - 23.55 What reaction conditions—base, solvent, and...Ch. 23 - Prob. 23.56PCh. 23 - 23.57 Draw a stepwise mechanism showing how two...Ch. 23 - 23.58 Draw a stepwise mechanism for the following...Ch. 23 - Prob. 23.59PCh. 23 - 23.60 Draw stepwise mechanisms illustrating how...Ch. 23 - Prob. 23.61PCh. 23 - Prob. 23.62PCh. 23 - 23.63 Synthesize each compound from cyclohexanone...Ch. 23 - Prob. 23.64PCh. 23 - Prob. 23.65PCh. 23 - 23.66 Synthesize (Z)-hept-5-en-2-one from ethyl...Ch. 23 - Prob. 23.67PCh. 23 - 23.68 Capsaicin, the spicy component of hot...Ch. 23 - 23.69 Treatment of W with , followed by , affords...Ch. 23 - Prob. 23.70PCh. 23 - Prob. 23.71PCh. 23 - Prob. 23.72PCh. 23 - Prob. 23.73PCh. 23 - Prob. 23.74P
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IR Spectroscopy; Author: Professor Dave Explains;https://www.youtube.com/watch?v=_TmevMf-Zgs;License: Standard YouTube License, CC-BY