Organic Chemistry
Organic Chemistry
8th Edition
ISBN: 9781305580350
Author: William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher: Cengage Learning
Question
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Chapter 6, Problem 6.42P

(a)

Interpretation Introduction

Interpretation:

The number and kind of stereoisomers formed when given molecule is treated in presence of Hg(OAc)2,H2OfollowedbyNaBH4 has to be identified. For given enantiomerically pure and optically active compound the formed product should be identified that it is optically active or inactive.

Concept Introduction:

Geometric isomers: Two atoms with the same side location of the double bond are called cis isomers and two atoms with opposite side locations of the double bond are called Trans isomers.

Organic Chemistry, Chapter 6, Problem 6.42P , additional homework tip  1

R and S nomenclature: it is used to assign the molecule using CIP (Cahn-Ingold-Prelog) rules.

The CIP rules are as follows:

Select the chiral carbon and assign the numbers according to the decreasing atomic mass of atoms attached to it.

If the numbering follows clockwise direction then the molecule is termed as R and if it follows anti-clockwise direction then molecule is termed as S.

(b)

Interpretation Introduction

Interpretation:

The number and kind of stereoisomers formed when given molecule is treated in presence of H2/Pt has to be identified. For given enantiomerically pure and optically active compound the formed product should be identified that it is optically active or inactive.

Concept Introduction:

Geometric isomers: Two atoms with the same side location of the double bond are called cis isomers and two atoms with opposite side locations of the double bond are called Trans isomers.

Organic Chemistry, Chapter 6, Problem 6.42P , additional homework tip  2

R and S nomenclature: it is used to assign the molecule using CIP (Cahn-Ingold-Prelog) rules.

The CIP rules are as follows:

Select the chiral carbon and assign the numbers according to the decreasing atomic mass of atoms attached to it.

If the numbering follows clockwise direction then the molecule is termed as R and if it follows anti-clockwise direction then molecule is termed as S.

(c)

Interpretation Introduction

Interpretation:

The number and kind of stereoisomers formed when given molecule is treated in presence of BH3 followed by H2O2inNaOH has to be identified. For given enantiomerically pure and optically active compound the formed product should be identified that it is optically active or inactive.

Concept Introduction:

Geometric isomers: Two atoms with the same side location of the double bond are called cis isomers and two atoms with opposite side locations of the double bond are called Trans isomers.

Organic Chemistry, Chapter 6, Problem 6.42P , additional homework tip  3

R and S nomenclature: it is used to assign the molecule using CIP (Cahn-Ingold-Prelog) rules.

The CIP rules are as follows:

Select the chiral carbon and assign the numbers according to the decreasing atomic mass of atoms attached to it.

If the numbering follows clockwise direction then the molecule is termed as R and if it follows anti-clockwise direction then molecule is termed as S.

(d)

Interpretation Introduction

Interpretation:

The number and kind of stereoisomers formed when given molecule is treated in presence of Br2 in CCl4 has to be identified. For given enantiomerically pure and optically active compound the formed product should be identified that it is optically active or inactive.

Concept Introduction:

Geometric isomers: Two atoms with the same side location of the double bond are called cis isomers and two atoms with opposite side locations of the double bond are called Trans isomers.

Organic Chemistry, Chapter 6, Problem 6.42P , additional homework tip  4

R and S nomenclature: it is used to assign the molecule using CIP (Cahn-Ingold-Prelog) rules.

The CIP rules are as follows:

Select the chiral carbon and assign the numbers according to the decreasing atomic mass of atoms attached to it.

If the numbering follows clockwise direction then the molecule is termed as R and if it follows anti-clockwise direction then molecule is termed as S.

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Chapter 6 Solutions

Organic Chemistry

Ch. 6.5 - Prob. 6.11PCh. 6.5 - Prob. 6.12PCh. 6.5 - What alkene with the molecular formula C6H12, when...Ch. 6 - Prob. 6.15PCh. 6 - Prob. 6.16PCh. 6 - Predict the organic product(s) of the reaction of...Ch. 6 - Prob. 6.18PCh. 6 - Prob. 6.20PCh. 6 - Draw a structural formula for an alkene with the...Ch. 6 - Account for the fact that addition of HCl to...Ch. 6 - Account for the fact that treating propenoic acid...Ch. 6 - Draw a structural formula for the alkene with the...Ch. 6 - Draw the alternative chair conformations for the...Ch. 6 - Draw a structural formula for the cycloalkene with...Ch. 6 - Reaction of this bicycloalkene with bromine in...Ch. 6 - Terpin, prepared commercially by the...Ch. 6 - Propose a mechanism for this reaction and account...Ch. 6 - Treating 2-methylpropene with methanol in the...Ch. 6 - When 2-pentene is treated with Cl2 in methanol,...Ch. 6 - Treating cyclohexene with HBr in the presence of...Ch. 6 - Propose a mechanism for this reaction. 1-Pentane...Ch. 6 - Treating 4-penten-1-ol with bromine in water forms...Ch. 6 - Prob. 6.35PCh. 6 - Prob. 6.36PCh. 6 - Reaction of -pinene with borane followed by...Ch. 6 - Write structural formulas for the major organic...Ch. 6 - Draw the structural formula of the alkene that...Ch. 6 - Consider the following reaction. (a) Draw a...Ch. 6 - Prob. 6.42PCh. 6 - Prob. 6.43PCh. 6 - Show how to convert ethylene to these compounds....Ch. 6 - Show how to convert cyclopentene into these...Ch. 6 - Prob. 6.46PCh. 6 - Describe the stereochemistry of the bromohydrin...Ch. 6 - Prob. 6.49PCh. 6 - Treating 1,3-butadiene with 1 mole of HBr gives a...Ch. 6 - In this chapter, we studied the mechanism of the...Ch. 6 - As we have seen in this chapter, carbon-carbon...Ch. 6 - Prob. 6.53PCh. 6 - Prob. 6.54P
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