Organic Chemistry
Organic Chemistry
6th Edition
ISBN: 9781936221349
Author: Marc Loudon, Jim Parise
Publisher: W. H. Freeman
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Chapter 6, Problem 6.47AP
Interpretation Introduction

(a)

Interpretation:

The reason as to why the catalytic hydrogenation reaction of ()-3-methyl-1-pentene results in the optically inactive product is to be stated.

Concept introduction:

A carbon atom that has four nonequivalent atoms or groups attached to it is known as the chiral carbon atom. Chiral carbon centers are also called asymmetric or stereogenic centers. The chiral atom sometimes results in the formation of enantiomers which are the non-superimposable mirror images of each other.

Interpretation Introduction

(b)

Interpretation:

The absolute configuration of (+)-3-methylhexane is to be stated when catalytic hydrogenation of (S)-(+)-3-methyl-1-hexene gives ()-3-methylhexane.

Concept introduction:

A carbon atom that has four nonequivalent atoms or groups attached to it is known as the chiral carbon atom. Chiral carbon centers are also called as asymmetric or stereogenic centers. The chiral atom sometimes results in the formation of enantiomers which are the non-superimposable mirror images of each other.

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a) When (Z)-3-methylhex-3-ene undergoes hydroboration–oxidation, two isomeric products are formed. Give their structures, and label each asymmetric carbon atom as (R) or (S). What is the relationship between these isomers?
(a) What product(s) are formed when the E isomer of C6H5CH = CHC6H5 is treated with Br2, followed by one equivalent of KOH? Label the resulting alkene(s) as E or Z. (b) What product(s) are formed when the Z isomer of C6H5CH = CHC6H5 is subjected to the same reaction sequence? (c) How are the compounds in parts (a) and (b) related to each other?
Draw the structures of the following molecules: (a) (S)-sec-butylcyclopentane (b) p-benzyltoluene c) (Z)-5-phenyl-3-methyl-3-octene
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