Organic Chemistry
Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Chapter 11.SE, Problem 81AP

The antipsychotic drug flupentixol is prepared by the following scheme:

Chapter 11.SE, Problem 81AP, The antipsychotic drug flupentixol is prepared by the following scheme:

Expert Solution
Check Mark
Interpretation Introduction

a)

The alkyl chloride, structure of D has to be identified and R and S configuration has to be assigned for the products.

Concept introduction:

R and S nomenclature: it is used to assign the molecule using CIP 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.

Chiral: A molecule is non superimposable on its mirror image is called chiral molecule.

Four different atoms attached to a carbon atom is called chiral molecule.

Isomer: A molecule having the same molecular formula but with different chemical structure is called isomer.

Stereoisomers: Stereoisomers are molecules that have the same molecular formula and they differ only in arrangement of atom in three-dimensional space.

Enantiomers: A compound which is non-superimposable mirror image is called enantiomers.

Diastereomers: A compound which is non-superimposable and non-mirror image is called diastereomers.

Racemic mixture: A racemic mixture is simply a mixture containing an equal amount of each enantiomer.

Achiral: A molecule is superimposable on its mirror image is called achiral molecule.

Answer to Problem 81AP

The reaction is given below,

Organic Chemistry, Chapter 11.SE, Problem 81AP , additional homework tip  1

Explanation of Solution

Given information:

The given reactant shown below,

Organic Chemistry, Chapter 11.SE, Problem 81AP , additional homework tip  2

The given compound (A) reacts with chloro propanol gives the compound (C).

The reaction is given below,

Organic Chemistry, Chapter 11.SE, Problem 81AP , additional homework tip  3

Conclusion

The alkyl chloride, structure of D is given and R and S configuration is assigned for the products.

Expert Solution
Check Mark
Interpretation Introduction

b)

Interpretation:

The alkyl chloride, structure of D has to be identified and R and S configuration has to be assigned for the products.

Concept introduction:

R and S nomenclature: it is used to assign the molecule using CIP 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.

Chiral: A molecule is non superimposable on its mirror image is called chiral molecule.

Four different atoms attached to a carbon atom is called chiral molecule.

Isomer: A molecule having the same molecular formula but with different chemical structure is called isomer.

Stereoisomers: Stereoisomers are molecules that have the same molecular formula and they differ only in arrangement of atom in three-dimensional space.

Enantiomers: A compound which is non-superimposable mirror image is called enantiomers.

Diastereomers: A compound which is non-superimposable and non-mirror image is called diastereomers.

Racemic mixture: A racemic mixture is simply a mixture containing an equal amount of each enantiomer.

Achiral: A molecule is superimposable on its mirror image is called achiral molecule.

Answer to Problem 81AP

The Grignard reagent is given below,

Organic Chemistry, Chapter 11.SE, Problem 81AP , additional homework tip  4

Explanation of Solution

Given information:

The given reactant shown below,

Organic Chemistry, Chapter 11.SE, Problem 81AP , additional homework tip  5

The Grignard reagent is given below,

The compound (c) reaction with thionyl chloride gives chlorinated compound, then it is reacting with magnesium gives the Grignard reagent (D).

Organic Chemistry, Chapter 11.SE, Problem 81AP , additional homework tip  6

Conclusion

The alkyl chloride, structure of D is given and R and S configuration is assigned for the products.

Expert Solution
Check Mark
Interpretation Introduction

c)

Interpretation

The alkyl chloride, structure of D has to be identified and R and S configuration has to be assigned for the products.

Concept introduction:

R and S nomenclature: it is used to assign the molecule using CIP 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.

Chiral: A molecule is non superimposable on its mirror image is called chiral molecule.

Four different atoms attached to a carbon atom is called chiral molecule.

Isomer: A molecule having the same molecular formula but with different chemical structure is called isomer.

Stereoisomers: Stereoisomers are molecules that have the same molecular formula and they differ only in arrangement of atom in three-dimensional space.

Enantiomers: A compound which is non-superimposable mirror image is called enantiomers.

Diastereomers: A compound which is non-superimposable and non-mirror image is called diastereomers.

Racemic mixture: A racemic mixture is simply a mixture containing an equal amount of each enantiomer.

Achiral: A molecule is superimposable on its mirror image is called achiral molecule.

Answer to Problem 81AP

The pair of enantiomers is given below,

Organic Chemistry, Chapter 11.SE, Problem 81AP , additional homework tip  7

Explanation of Solution

Given information:

The given reactant shown below,

Organic Chemistry, Chapter 11.SE, Problem 81AP , additional homework tip  8

The pair of enantiomers is given below,

The compound (D) reaction with compound (E) gives enantiomer of corresponding products.

Organic Chemistry, Chapter 11.SE, Problem 81AP , additional homework tip  9

Conclusion

The alkyl chloride, structure of D is given and R and S configuration is assigned for the products.

Expert Solution
Check Mark
Interpretation Introduction

d)

Interpretation:

The alkyl chloride, structure of D has to be identified and R and S configuration has to be assigned for the products.

Concept introduction:

R and S nomenclature: it is used to assign the molecule using CIP 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.

Chiral: A molecule is non superimposable on its mirror image is called chiral molecule.

Four different atoms attached to a carbon atom is called chiral molecule.

Isomer: A molecule having the same molecular formula but with different chemical structure is called isomer.

Stereoisomers: Stereoisomers are molecules that have the same molecular formula and they differ only in arrangement of atom in three-dimensional space.

Enantiomers: A compound which is non-superimposable mirror image is called enantiomers.

Diastereomers: A compound which is non-superimposable and non-mirror image is called diastereomers.

Racemic mixture: A racemic mixture is simply a mixture containing an equal amount of each enantiomer.

Achiral: A molecule is superimposable on its mirror image is called achiral molecule.

Answer to Problem 81AP

The compound (F) undergoes hydrolysis reaction gives E and Z isomers of corresponding products.

Organic Chemistry, Chapter 11.SE, Problem 81AP , additional homework tip  10

Explanation of Solution

Given information:

The given reactant shown below,

Organic Chemistry, Chapter 11.SE, Problem 81AP , additional homework tip  11

The compound (F) undergoes hydrolysis reaction gives E and Z isomers of corresponding products.

Organic Chemistry, Chapter 11.SE, Problem 81AP , additional homework tip  12

Conclusion

The alkyl chloride, structure of D is given and R and S configuration is assigned for the products.

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Chapter 11 Solutions

Organic Chemistry

Ch. 11.5 - Rank the following substances in order of their...Ch. 11.5 - 3-Bromo-1-butene and 1-bromo-2-butene undergo SN1...Ch. 11.5 - Prob. 13PCh. 11.6 - Review the mechanism of geraniol biosynthesis...Ch. 11.7 - Prob. 15PCh. 11.7 - What alkyl halides might the following alkenes...Ch. 11.8 - Prob. 17PCh. 11.8 - Prob. 18PCh. 11.9 - Prob. 19PCh. 11.12 - Prob. 20PCh. 11.SE - Prob. 21VCCh. 11.SE - From what alkyl bromide was the following alkyl...Ch. 11.SE - Prob. 23VCCh. 11.SE - Prob. 24VCCh. 11.SE - Prob. 25MPCh. 11.SE - Prob. 26MPCh. 11.SE - Prob. 27MPCh. 11.SE - Prob. 28MPCh. 11.SE - Prob. 29MPCh. 11.SE - Prob. 30MPCh. 11.SE - Prob. 31MPCh. 11.SE - Prob. 32MPCh. 11.SE - Metabolism of S-adenosylhomocysteine (Section...Ch. 11.SE - Reaction of iodoethane with CN- yields a small...Ch. 11.SE - One step in the urea cycle for ridding the body of...Ch. 11.SE - Prob. 36MPCh. 11.SE - Prob. 37MPCh. 11.SE - Propose a mechanism for the following reaction, an...Ch. 11.SE - Prob. 39APCh. 11.SE - The following Walden cycle has been carried out....Ch. 11.SE - Prob. 41APCh. 11.SE - Which reactant in each of the following pairs is...Ch. 11.SE - Prob. 43APCh. 11.SE - Prob. 44APCh. 11.SE - Prob. 45APCh. 11.SE - Prob. 46APCh. 11.SE - Prob. 47APCh. 11.SE - Prob. 48APCh. 11.SE - Propose structures for compounds that fit the...Ch. 11.SE - What products would you expect from the reaction...Ch. 11.SE - Prob. 51APCh. 11.SE - Prob. 52APCh. 11.SE - Prob. 53APCh. 11.SE - Prob. 54APCh. 11.SE - Prob. 55APCh. 11.SE - Order each of the following sets of compounds with...Ch. 11.SE - Order each of the following sets of compounds with...Ch. 11.SE - Prob. 58APCh. 11.SE - Prob. 59APCh. 11.SE - Ethers can often be prepared by SN2 reaction of...Ch. 11.SE - Show the stereochemistry of the epoxide (see...Ch. 11.SE - Prob. 62APCh. 11.SE - In addition to not undergoing substitution...Ch. 11.SE - The tosylate of (2R, 3S)-3-phenyl-2-butanol...Ch. 11.SE - Prob. 65APCh. 11.SE - Prob. 66APCh. 11.SE - Prob. 67APCh. 11.SE - Prob. 68APCh. 11.SE - Prob. 69APCh. 11.SE - (S)-2-Butanol slowly racemizes on standing in...Ch. 11.SE - Reaction of HBr with (R)-3-methyl-3-hexanol leads...Ch. 11.SE - Treatment of 1-bromo-2-deuterio-2-phenylethane...Ch. 11.SE - Prob. 73APCh. 11.SE - Prob. 74APCh. 11.SE - In light of your answer to Problem 11-74, explain...Ch. 11.SE - Prob. 76APCh. 11.SE - Compound X is optically inactive and has the...Ch. 11.SE - When a primary alcohol is treated with...Ch. 11.SE - Prob. 79APCh. 11.SE - Amines are converted into alkenes by a two-step...Ch. 11.SE - The antipsychotic drug flupentixol is prepared by...
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