Organic Chemistry -Study Guide / Solution Manual (Custom)
Organic Chemistry -Study Guide / Solution Manual (Custom)
4th Edition
ISBN: 9781259141072
Author: SMITH
Publisher: MCG
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Chapter 9, Problem 9.55P
Interpretation Introduction

Interpretation: A step wise, detailed mechanism for the given reaction is to be stated.

Concept introduction: Alcohols undergo dehydration reaction in the presence of strong acids like H2SO4 or p-toluenesulfonicacid(TsOH) and yield alkenes. The mechanism of the reaction involves three steps. The first step is protonation of the oxygen atom to convert poor leaving group into good leaving group. The second step is heterolysis cleavage of CO bond to form a carbocation intermediate. The third step is abstraction of proton from a carbon adjacent to the carbocation to form desired product.

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Chapter 9 Solutions

Organic Chemistry -Study Guide / Solution Manual (Custom)

Ch. 9 - Prob. 9.11PCh. 9 - Prob. 9.12PCh. 9 - Prob. 9.13PCh. 9 - Prob. 9.14PCh. 9 - Problem 9.13 Draw the structure of each...Ch. 9 - What other alkene is also formed along with Y in...Ch. 9 - Prob. 9.17PCh. 9 - Explain how the reaction of CH32CHCHCl CH3 with...Ch. 9 - Prob. 9.19PCh. 9 - Draw the products of each reaction, indicating the...Ch. 9 - Problem 9.19 What is the major product formed...Ch. 9 - Prob. 9.22PCh. 9 - Prob. 9.23PCh. 9 - Problem 9.22 Draw the organic products formed in...Ch. 9 - Problem 9.23 Draw two steps to convert into each...Ch. 9 - Draw the products of each reaction, and indicate...Ch. 9 - Draw the products of each reaction, and include...Ch. 9 - Draw the products formed when (S)-butan-2-ol is...Ch. 9 - Prob. 9.29PCh. 9 - Prob. 9.30PCh. 9 - Explain why the treatment of anisole with HBr...Ch. 9 - Prob. 9.32PCh. 9 - The cis and trans isomers of 2, 3-dimethyloxirane...Ch. 9 - Problem 9.36 Draw the product of each...Ch. 9 - 9.37 Name each compound depicted in the...Ch. 9 - Answer each question using the ball-and-stick...Ch. 9 - Prob. 9.37PCh. 9 - a. Draw the structure of 1, 2, and 3 alcohol with...Ch. 9 - Give IUPAC name for each alcohol. a....Ch. 9 - Name each ether and epoxide. a.b.c.d.Ch. 9 - Prob. 9.41PCh. 9 - Draw the eight constitutional isomers with...Ch. 9 - Rank each group of compounds in order of: a....Ch. 9 - Prob. 9.44PCh. 9 - 9.44 Why is the boiling point of higher than...Ch. 9 - Draw the organic products formed when CH3CH2CH2OH...Ch. 9 - Draw the organic products formed when 1-methyl...Ch. 9 - What alkenes are formed when each alcohol is...Ch. 9 - Prob. 9.49PCh. 9 - Prob. 9.50PCh. 9 - 9.48 Draw the products of each reaction and...Ch. 9 - Prob. 9.52PCh. 9 - 9.52 Draw a stepwise mechanism for the following...Ch. 9 - 9.53 Although alcohol V gives a single alkene W...Ch. 9 - Prob. 9.55PCh. 9 - Prob. 9.56PCh. 9 - Prob. 9.57PCh. 9 - When CH3CH2CH2CH2OH is treated with H2SO4 NaBr,...Ch. 9 - 9.57 Draw a stepwise, detailed mechanism for the...Ch. 9 - Prob. 9.60PCh. 9 - Draw two different routes to each of the following...Ch. 9 - Prob. 9.62PCh. 9 - Prob. 9.63PCh. 9 - 9.62 Draw a stepwise mechanism for each...Ch. 9 - Draw a stepwise, detailed mechanism for the...Ch. 9 - Prob. 9.66PCh. 9 - Draw the products of each reaction. a.c. b.d.Ch. 9 - When each halohydrin is treated with, a product of...Ch. 9 - Prob. 9.69PCh. 9 - Devise a stepwise mechanism for the following...Ch. 9 - Draw the products of each reaction, and indicate...Ch. 9 - Prepare each compound from CH3CH2CH2CH2OH. More...Ch. 9 - Prepare each compound from cyclopentanol. More...Ch. 9 - 9.72 Identify the reagents (a–h) needed to carry...Ch. 9 - Prob. 9.75PCh. 9 - 9.74 Treatment of with affords compound A and ....Ch. 9 - Prob. 9.77PCh. 9 - Prob. 9.78PCh. 9 - 9.77 Draw a stepwise, detailed mechanism for the...Ch. 9 - Dehydration of 1, 2, 2-trimethylcyclohexanol with...Ch. 9 - Prob. 9.81PCh. 9 - 9.80 Draw a stepwise mechanism for the following...Ch. 9 - 9.81 Aziridines are heterocycles that contain an...