Pearson eText for Essential Organic Chemistry -- Instant Access (Pearson+)
Pearson eText for Essential Organic Chemistry -- Instant Access (Pearson+)
3rd Edition
ISBN: 9780137533268
Author: Paula Bruice
Publisher: PEARSON+
Question
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Chapter 6.6, Problem 14P

(a)

Interpretation Introduction

Interpretation:

The stereoisomer products for the given reaction have to be determined.

Concept introduction:

Nucleophile: Nucleophiles are electron rich compounds which donates electrons to electrophilic compounds which results in bond formation.

Electrophile: Electrophiles are electron deficient compounds which accepts electrons from nucleophiles that results in bond formation.

Electrophilic addition: It is a type of addition reaction in which the pi bond present in the molecule breaks as the electrophile approaches and results in the formation of product with sigma bond.

In addition reaction of alkenes when two substituents approaches same side of C=C then it is named as syn addition if it is on opposite sides of C=C it is defined as anti-addition.

E configuration: The geometric isomers are given E configuration if high priority groups are placed on opposite sides of the bond.

Z configuration: The geometric isomers are given Z configuration if high priority groups are placed on same sides of the bond.

Erythro Product: It is the representation of carbohydrates in Fischer projection when two same substituents are placed on the same side.

Threo Product: It is the representation of carbohydrates in Fischer projection when two same substituents are placed on opposite side.

Stereo specific: The reaction is considered as stereo specific if the reactant is stereo isomers that give rise to different set of stereo isomers.

Stereoisomers: Two compounds with same molecular formula but different in their orientation are considered as isomers.

The presence of atom with non-super impossible mirror image is defined as enantiomers which are given R and S configuration based on the atoms bonded with them.

(b)

Interpretation Introduction

Interpretation:

The stereoisomer products for the given reaction have to be determined.

Concept introduction:

Nucleophile: Nucleophiles are electron rich compounds which donates electrons to electrophilic compounds which results in bond formation.

Electrophile: Electrophiles are electron deficient compounds which accepts electrons from nucleophiles that results in bond formation.

Electrophilic addition: It is a type of addition reaction in which the pi bond present in the molecule breaks as the electrophile approaches and results in the formation of product with sigma bond.

In addition reaction of alkenes when two substituents approaches same side of C=C then it is named as syn addition if it is on opposite sides of C=C it is defined as anti-addition.

E configuration: The geometric isomers are given E configuration if high priority groups are placed on opposite sides of the bond.

Z configuration: The geometric isomers are given Z configuration if high priority groups are placed on same sides of the bond.

Stereo specific: The reaction is considered as stereo specific if the reactant is stereo isomers that give rise to different set of stereo isomers.

Stereoisomers: Two compounds with same molecular formula but different in their orientation are considered as isomers.

The presence of atom with non-super impossible mirror image is defined as enantiomers which are given R and S configuration based on the atoms bonded with them.

(c)

Interpretation Introduction

Interpretation:

The stereoisomer products for the given reaction have to be determined.

Concept introduction:

Nucleophile: Nucleophiles are electron rich compounds which donates electrons to electrophilic compounds which results in bond formation.

Electrophile: Electrophiles are electron deficient compounds which accepts electrons from nucleophiles that results in bond formation.

Electrophilic addition: It is a type of addition reaction in which the pi bond present in the molecule breaks as the electrophile approaches and results in the formation of product with sigma bond.

Carbocation: it is carbon ion that bears a positive charge on it.

Carbocation stability order:

Pearson eText for Essential Organic Chemistry -- Instant Access (Pearson+), Chapter 6.6, Problem 14P

(d)

Interpretation Introduction

Interpretation:

The stereoisomer products for the given reaction have to be determined.

Concept introduction:

Nucleophile: Nucleophiles are electron rich compounds which donates electrons to electrophilic compounds which results in bond formation.

Electrophile: Electrophiles are electron deficient compounds which accepts electrons from nucleophiles that results in bond formation.

Electrophilic addition: It is a type of addition reaction in which the pi bond present in the molecule breaks as the electrophile approaches and results in the formation of product with sigma bond.

In addition reaction of alkenes when two substituents approaches same side of C=C then it is named as syn addition if it is on opposite sides of C=C it is defined as anti-addition.

E configuration: The geometric isomers are given E configuration if high priority groups are placed on opposite sides of the bond.

Threo Product: It is the representation of carbohydrates in Fischer projection when two same substituents are placed on opposite side.

Stereo specific: The reaction is considered as stereo specific if the reactant is stereo isomers that give rise to different set of stereo isomers.

Stereoisomers: Two compounds with same molecular formula but different in their orientation are considered as isomers.

The presence of atom with non-super impossible mirror image is defined as enantiomers which are given R and S configuration based on the atoms bonded with them.

(e)

Interpretation Introduction

Interpretation:

The stereoisomer products for the given reaction have to be determined.

Concept introduction:

Nucleophile: Nucleophiles are electron rich compounds which donates electrons to electrophilic compounds which results in bond formation.

Electrophile: Electrophiles are electron deficient compounds which accepts electrons from nucleophiles that results in bond formation.

Electrophilic addition: It is a type of addition reaction in which the pi bond present in the molecule breaks as the electrophile approaches and results in the formation of product with sigma bond.

In addition reaction of alkenes when two substituents approaches same side of C=C then it is named as syn addition if it is on opposite sides of C=C it is defined as anti-addition.

E configuration: The geometric isomers are given E configuration if high priority groups are placed on opposite sides of the bond.

Z configuration: The geometric isomers are given Z configuration if high priority groups are placed on same sides of the bond.

Erythro Product: It is the representation of carbohydrates in Fischer projection when two same substituents are placed on the same side.

Threo Product: It is the representation of carbohydrates in Fischer projection when two same substituents are placed on opposite side.

Stereo specific: The reaction is considered as stereo specific if the reactant is stereo isomers that give rise to different set of stereo isomers.

Stereoisomers: Two compounds with same molecular formula but different in their orientation are considered as isomers.

The presence of atom with non-super impossible mirror image is defined as enantiomers which are given R and S configuration based on the atoms bonded with them.

(f)

Interpretation Introduction

Interpretation:

The stereoisomer products for the given reaction have to be determined.

Concept introduction:

Nucleophile: Nucleophiles are electron rich compounds which donates electrons to electrophilic compounds which results in bond formation.

Electrophile: Electrophiles are electron deficient compounds which accepts electrons from nucleophiles that results in bond formation.

Electrophilic addition: It is a type of addition reaction in which the pi bond present in the molecule breaks as the electrophile approaches and results in the formation of product with sigma bond.

In addition reaction of alkenes when two substituents approaches same side of C=C then it is named as syn addition if it is on opposite sides of C=C it is defined as anti-addition.

E configuration: The geometric isomers are given E configuration if high priority groups are placed on opposite sides of the bond.

Z configuration: The geometric isomers are given Z configuration if high priority groups are placed on same sides of the bond.

Stereo specific: The reaction is considered as stereo specific if the reactant is stereo isomers that give rise to different set of stereo isomers.

Stereoisomers: Two compounds with same molecular formula but different in their orientation are considered as isomers.

The presence of atom with non-super impossible mirror image is defined as enantiomers which are given R and S configuration based on the atoms bonded with them.

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Draw the products of the following reactions. If the products can exist as stereoisomers show what stereoisomers are formed. a. cis-2-pentene + Br2/CH2Cl2              b. trans-2-pentene + Br2/CH2Cl2 c. 1- butene + HCl                              d. methylcyclohexene + HBr  e. trans-3-hexene + Br2/CH2Cl2          f. cis-3-hexene + Br2/CH2Cl2 g. 3,3-dimethyl-1-pentene + HBr       h. cis-2-butene + HBr i. (Z)-2,3-dichloro-2-butene + H2, Pd/C     j. (E)-2,3-dichloro-2-butene + H2, Pd/C k. (Z)-3,4-dimethyl-3-hexene + H2, Pd/C    l. (E)-3,4-dimethyl-3-hexene + H2, Pd/C
h. 3-methyl-1-butene with Hg(OAC)2 and CH3OH, followed later by NaBH4 CH3 H2C=CH-CH-CH3 Major Product(s) of h. Stereochemistry of the product described in h. (Circle one) а. R b. S С. Е d. Z e. a mixture of E and Z f. erythro g. threo h. a racemic (50/50) mixture i. all 4 products (a set of erythro and a set of threo) j. no stereochemistry
g. cis-3-methylpent-2-ene with BH3, H2O2, and OH CH3 H3C- CH =C -CH2-CH3 Major Product(s) of g. Stereochemistry of the product described in g. (Circle one) а. R b. S С. Е d. Z e. a mixture of E and Z f. erythro g. threo h. a racemic (50/50) mixture i. all 4 products (a set of erythro and a set of threo) j. no stereochemistry

Chapter 6 Solutions

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