ORGANIC CHEMISTRY SOLUTION MANUAL
ORGANIC CHEMISTRY SOLUTION MANUAL
16th Edition
ISBN: 9781260036510
Author: SMITH
Publisher: MCG
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Textbook Question
Chapter 9, Problem 9.1P

Label each ether and alcohol in brevenal, a marine natural product. Classify each alcohol as 1 ο , 2 ο , or 3 ο .

Chapter 9, Problem 9.1P, Problem 9.1 Label each ether and alcohol in brevenal, a marine natural product. Classify each

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Interpretation Introduction

Interpretation: Each ether and alcohol in brevenal is to be labeled and each alcohol is to be classified as 1°,2°,or3°.

Concept introduction: Alcohols and ethers are the functional groups that involve CO, σ bonds. Alcohols involve a hydroxyl group (OH) bonded to an sp3 hybridized C atom. They are classified as 1°,2°,or3° on the basis of number of C atoms bonded to the carbon with the hydroxyl group. Ethers have two aryl or alkyl groups bonded to an O atom.

Answer to Problem 9.1P

Each ether and alcohol in brevenal is labeled as shown below.

ORGANIC CHEMISTRY SOLUTION MANUAL, Chapter 9, Problem 9.1P , additional homework tip  1

Explanation of Solution

The structure of brevenal (given compound) is,

ORGANIC CHEMISTRY SOLUTION MANUAL, Chapter 9, Problem 9.1P , additional homework tip  2

Figure 1

Alcohols and ethers are the functional groups that involve CO σ bonds. Alcohols involve a hydroxyl group (OH) bonded to an sp3 hybridized C atom. Ethers have two aryl or alkyl groups bonded to an O atom. Thus, each ether and alcohol in brevenal is labeled as,

ORGANIC CHEMISTRY SOLUTION MANUAL, Chapter 9, Problem 9.1P , additional homework tip  3

Figure 2

Alcohols are classified as 1°,2°,or3° on the basis of number of C atoms bonded to the carbon atom with the hydroxyl group. In Figure 2, there are two alcohols. These alcohols are labeled with A and B in Figure 3.

ORGANIC CHEMISTRY SOLUTION MANUAL, Chapter 9, Problem 9.1P , additional homework tip  4

Figure 3

In Figure 3, the carbon atom of alcohol (A) is bonded to two C atoms and the carbon atom of alcohol (B) is bonded to three C atoms.

If the number of carbon atom bonded to the carbon atom with the hydroxyl group is one, then it is classified as 1° alcohol. If the number of carbon atom bonded to the carbon atom with the hydroxyl group is two, then it is classified as 2° alcohol. If the number of carbon atom bonded to the carbon atom with the hydroxyl group is three, then it is classified as 3° alcohol.

Thus, each alcohol in brevenal is classified as,

ORGANIC CHEMISTRY SOLUTION MANUAL, Chapter 9, Problem 9.1P , additional homework tip  5

Figure 4

Conclusion

Each ether and alcohol in brevenal is labeled in Figure 2.

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Chapter 9 Solutions

ORGANIC CHEMISTRY SOLUTION MANUAL

Ch. 9 - Problem 9.11 Draw the products formed when each...Ch. 9 - Prob. 9.12PCh. 9 - Problem 9.13 Draw the structure of each...Ch. 9 - What other alkene is also formed along with Y in...Ch. 9 - Prob. 9.15PCh. 9 - Explain why two substitution products are formed...Ch. 9 - Draw the products of each reaction. a. b. c.Ch. 9 - Problem 9.18 Draw the products of each reaction,...Ch. 9 - Problem 9.19 What is the major product formed...Ch. 9 - Prob. 9.20PCh. 9 - Prob. 9.21PCh. 9 - Problem 9.22 Draw the organic products formed in...Ch. 9 - Problem 9.23 Draw two steps to convert into each...Ch. 9 - Prob. 9.24PCh. 9 - Problem 9.25 Draw the products of each reaction,...Ch. 9 - Draw the products formed when (S)-butan-2-ol is...Ch. 9 - Draw the product formed when (CH3)2CHOH is treated...Ch. 9 - What alkyl halides are formed when each ether is...Ch. 9 - Explain why the treatment of anisole with HBr...Ch. 9 - Name each thiol. a. b. Ch. 9 - Draw the product of each reaction. ac b.d.Ch. 9 - Give the IUPAC name for each sulfide. a. b. Ch. 9 - Draw the product of each reaction. a. b. Ch. 9 - Prob. 9.34PCh. 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. 9.39PCh. 9 - 9.40 Give IUPAC name for each...Ch. 9 - Prob. 9.41PCh. 9 - Prob. 9.42PCh. 9 - Prob. 9.43PCh. 9 - 9.44 Why is the boiling point of higher than...Ch. 9 - 9.45 Draw the organic product(s) formed when is...Ch. 9 - 9.46 What alkenes are formed when each alcohol is...Ch. 9 - Prob. 9.47PCh. 9 - 9.48 Draw the products of each reaction and...Ch. 9 - 9.49 Draw the product of the following reaction,...Ch. 9 - Prob. 9.50PCh. 9 - Prob. 9.51PCh. 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. 9.54PCh. 9 - Prob. 9.55PCh. 9 - Prob. 9.56PCh. 9 - 9.57 Draw a stepwise, detailed mechanism for the...Ch. 9 - Prob. 9.58PCh. 9 - 9.59 Draw two different routes to each of the...Ch. 9 - Prob. 9.60PCh. 9 - 9.61 Draw the products formed when each ether is...Ch. 9 - 9.62 Draw a stepwise mechanism for each...Ch. 9 - Draw a stepwise, detailed mechanism for the...Ch. 9 - Prob. 9.64PCh. 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. 9.67PCh. 9 - Prob. 9.68PCh. 9 - Prob. 9.69PCh. 9 - Prob. 9.70PCh. 9 - Prepare each compound from cyclopentanol. More...Ch. 9 - 9.72 Identify the reagents (a–h) needed to carry...Ch. 9 - Prob. 9.73PCh. 9 - 9.74 Treatment of with affords compound A and ....Ch. 9 - Prob. 9.75PCh. 9 - Prob. 9.76PCh. 9 - 9.77 Draw a stepwise, detailed mechanism for the...Ch. 9 - 9.78 Dehydration of with affords as a minor...Ch. 9 - Prob. 9.79PCh. 9 - 9.80 Draw a stepwise mechanism for the following...Ch. 9 - 9.81 Aziridines are heterocycles that contain an...
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