Organic Chemistry
Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
Question
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Chapter 10.SE, Problem 16VC
Interpretation Introduction

Interpretation:

The alkyl beromide shown is prepared by treating (S)-2-pentanol with PBr3. The name of the alkyl bromide and its stereochemistry whether R or S are to be stated. Further whether there is any change in stereochemistry during the course of the reaction is also to be stated.

Concept introduction:

The alkyl halides are named using the following guidelines. The longest continuous carbon chain in the molecule is chosen. The chain is numbered from the end which gives lowest number to the substituent either halo or alkyl group present.

For assigning the configuration as R or S, the four groups attached to the chiral carbon are arranged in the order of preference based on the sequence rules. The molecule is viewed by orienting the molecule in such a way that the group of lowest ranking points away from the observer. If the arrangement of the groups of first, second and third ranking (1->2->3-) is clockwise R configuration is assigned. If their arrangement is anti-clockwise then S configuration is assigned.

If both the reactants and products of a reaction have same configuration the reaction is said to occur with retention in stereochemistry. If they have different configurations the reaction is said to occur with inversion in stereochemistry.

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Chapter 10 Solutions

Organic Chemistry

Ch. 10.7 - How would you carry out the following...Ch. 10.8 - Rank both sets of compounds in order of increasing...Ch. 10.8 - Tell whether each of the following reactions is an...Ch. 10.SE - Prob. 14VCCh. 10.SE - Prob. 15VCCh. 10.SE - Prob. 16VCCh. 10.SE - Draw the electron-pushing mechanism for each...Ch. 10.SE - Draw the electron-pushing mechanism for the...Ch. 10.SE - The formation of Br2 from NBS first involves the...Ch. 10.SE - In light of the fact that tertiary alkyl halides...Ch. 10.SE - Alkyl halides can be reduced to alkanes by a...Ch. 10.SE - Name the following alkyl halides:Ch. 10.SE - Prob. 23APCh. 10.SE - Draw and name all of the monochlorination products...Ch. 10.SE - How would you prepare the following compounds,...Ch. 10.SE - Prob. 26APCh. 10.SE - A chemist requires a large amount of...Ch. 10.SE - What product(s) would you expect from the reaction...Ch. 10.SE - What product(s) would you expect from the reaction...Ch. 10.SE - What product would you expect from the reaction of...Ch. 10.SE - Rank the compounds in each of the following series...Ch. 10.SE - Which of the following compounds have the same...Ch. 10.SE - Tell whether each of the following reactions is an...Ch. 10.SE - Prob. 34APCh. 10.SE - Alkylbenzenes such as toluene (methylbenzene)...Ch. 10.SE - Prob. 36APCh. 10.SE - Prob. 37APCh. 10.SE - Prob. 38APCh. 10.SE - Prob. 39APCh. 10.SE - Prob. 40APCh. 10.SE - The syntheses shown here are unlikely to occur as...Ch. 10.SE - Why do you suppose its not possible to prepare a...Ch. 10.SE - Prob. 43APCh. 10.SE - Identify the reagents a–c in the following...Ch. 10.SE - Prob. 45APCh. 10.SE - Prob. 46APCh. 10.SE - Prob. 47APCh. 10.SE - The relative rate of radical bromination is...Ch. 10.SE - Prob. 49APCh. 10.SE - Predict the product and provide the entire...
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