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The antipsychotic drug flupentixol is prepared by the following scheme:
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,
Explanation of Solution
Given information:
The given reactant shown below,
The given compound (A) reacts with chloro propanol gives the compound (C).
The reaction is given below,
The alkyl chloride, structure of D is given and R and S configuration is assigned for the products.
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,
Explanation of Solution
Given information:
The given reactant shown below,
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).
The alkyl chloride, structure of D is given and R and S configuration is assigned for the products.
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,
Explanation of Solution
Given information:
The given reactant shown below,
The pair of enantiomers is given below,
The compound (D) reaction with compound (E) gives enantiomer of corresponding products.
The alkyl chloride, structure of D is given and R and S configuration is assigned for the products.
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.
Explanation of Solution
Given information:
The given reactant shown below,
The compound (F) undergoes hydrolysis reaction gives E and Z isomers of corresponding products.
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
Bundle: Organic Chemistry, Loose-leaf Version, 9th + LMS Integrated for OWLv2, 4 terms (24 months) Printed Access Card
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Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning