Organic Chemistry (8th Edition)
Organic Chemistry (8th Edition)
8th Edition
ISBN: 9780134042282
Author: Paula Yurkanis Bruice
Publisher: PEARSON
Question
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Chapter 6.13, Problem 36P

(a)

Interpretation Introduction

Interpretation:

It should be identified that the reaction between 2-butene and  HBr is regioselective or not.

Concept introduction:

Regioselective: The reaction is considered as regioselective if it gives rise to specific constitutional isomer.

Constitutional Isomers: Two compounds are considered as constitutional isomers if they have same molecular formula but different in their connectivity.

Addition Reaction: It is defined as chemical reaction in which two given molecules combines and forms product. The types of addition reactions are electrophilic addition, nucleophilic addition, free radical additions and cycloadditions. Generally, compounds with carbon-hetero atom bonds favors addition reaction.

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

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

Carbocation stability order:

Organic Chemistry (8th Edition), Chapter 6.13, Problem 36P , additional homework tip  1

(b)

Interpretation Introduction

Interpretation:

It should be identified that the reaction between 2-butene and  HBr is stereo selective or not.

Concept introduction:

Stereo selective: The reaction is considered as stereo selective if it gives rise to only specific stereo isomer.

Addition Reaction: It is defined as chemical reaction in which two given molecules combines and forms product. The types of addition reactions are electrophilic addition, nucleophilic addition, free radical additions and cycloadditions. Generally, compounds with carbon-hetero atom bonds favors addition reaction.

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

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

Geometric isomers: Two compounds are considered as geometric isomers of each other if both contains same number of atoms but different in their arrangement that is compound is regarded as cis if identical substituents are placed on same side and trans if they are placed on the opposite sides.

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.

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.

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

Carbocation stability order:

Organic Chemistry (8th Edition), Chapter 6.13, Problem 36P , additional homework tip  2

(c)

Interpretation Introduction

Interpretation:

It should be identified that the reaction between 2-butene and  HBr is stereo specific or not.

Concept introduction:

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

Addition Reaction: It is defined as chemical reaction in which two given molecules combines and forms product. The types of addition reactions are electrophilic addition, nucleophilic addition, free radical additions and cycloadditions. Generally, compounds with carbon-hetero atom bonds favors addition reaction.

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

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

Geometric isomers: Two compounds are considered as geometric isomers of each other if both contains same number of atoms but different in their arrangement that is compound is regarded as cis if identical substituents are placed on same side and trans if they are placed on the opposite sides.

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.

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.

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

Carbocation stability order:

Organic Chemistry (8th Edition), Chapter 6.13, Problem 36P , additional homework tip  3

(d)

Interpretation Introduction

Interpretation:

It should be identified that the reaction between 1-butene and  HBr is regioselective or not.

Concept introduction:

Regioselective: The reaction is considered as regioselective if it gives rise to specific constitutional isomer.

Geometric isomers: Two compounds are considered as geometric isomers of each other if both contains same number of atoms but different in their arrangement that is compound is regarded as cis if identical substituents are placed on same side and trans if they are placed on the opposite sides.

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.

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.

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

Carbocation stability order:

Organic Chemistry (8th Edition), Chapter 6.13, Problem 36P , additional homework tip  4

(e)

Interpretation Introduction

Interpretation:

It should be identified that the reaction between 1-butene and  HBr is stereo selective or not.

Concept introduction:

Stereo selective: The reaction is considered as stereo selective if it gives rise to only specific stereo isomer.

Geometric isomers: Two compounds are considered as geometric isomers of each other if both contains same number of atoms but different in their arrangement that is compound is regarded as cis if identical substituents are placed on same side and trans if they are placed on the opposite sides.

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.

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.

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

Carbocation stability order:

Organic Chemistry (8th Edition), Chapter 6.13, Problem 36P , additional homework tip  5

(f)

Interpretation Introduction

Interpretation:

It should be identified that the reaction between 1-butene and  HBr is stereo specific or not.

Concept introduction:

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

Geometric isomers: Two compounds are considered as geometric isomers of each other if both contains same number of atoms but different in their arrangement that is compound is regarded as cis if identical substituents are placed on same side and trans if they are placed on the opposite sides.

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.

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.

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

Carbocation stability order:

Organic Chemistry (8th Edition), Chapter 6.13, Problem 36P , additional homework tip  6

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Students have asked these similar questions
(a) Draw all constitutional isomers formed by monochlorination of each alkane with Cl2 and hν. (b) Draw the major monobromination product formed by heating each alkane with Br2.
Which group in each pair is assigned the higher priority? a. – CH3, – CH2CH3 b. – I, – Br c. – H, – D d. – CH2Br, – CH2CH2Br e. – CH2CH2Cl, – CH2CH(CH3)2 f. – CH2OH, – CHO
A is a toxin produced by the poisonous seaweed Chlorodesmis fastigiata. (a) Label each alkene that exhibits stereoisomerism as E or Z. (b) Draw a stereoisomer of A that has all Z double bonds.

Chapter 6 Solutions

Organic Chemistry (8th Edition)

Ch. 6.5 - Prob. 11PCh. 6.6 - a. What is the major product or each or the...Ch. 6.6 - Prob. 14PCh. 6.6 - Prob. 15PCh. 6.7 - What is the major product obtained from the...Ch. 6.8 - Which is more highly regionselective: reaction of...Ch. 6.8 - Prob. 19PCh. 6.9 - What will be the product of the preceding reaction...Ch. 6.9 - Prob. 21PCh. 6.9 - Prob. 22PCh. 6.9 - Prob. 23PCh. 6.9 - What is the product of the addition of 1Cl to...Ch. 6.9 - What will be the major product obtained from the...Ch. 6.9 - Propose a mechanism for the following reaction:Ch. 6.10 - Draw structures for the following: a. 24...Ch. 6.10 - What alkene would you treat with a peroxyacid in...Ch. 6.11 - What products are formed when the following...Ch. 6.11 - Prob. 31PCh. 6.11 - Prob. 32PCh. 6.11 - The following product was obtained from the...Ch. 6.12 - What characteristics must the reactant of a...Ch. 6.13 - Prob. 36PCh. 6.13 - What stereoisomers are obtained from each of the...Ch. 6.13 - Prob. 41PCh. 6.13 - Prob. 42PCh. 6.13 - Prob. 43PCh. 6.13 - Prob. 45PCh. 6.13 - Prob. 46PCh. 6.13 - Prob. 47PCh. 6.13 - Prob. 48PCh. 6.13 - Prob. 49PCh. 6.13 - Prob. 50PCh. 6.14 - Prob. 51PCh. 6.16 - Prob. 53PCh. 6.16 - Explain why 3-methykyclohexene should not be used...Ch. 6 - Prob. 55PCh. 6 - Prob. 56PCh. 6 - Prob. 57PCh. 6 - What is the major product of the reaction of...Ch. 6 - Give two names for each of the following:Ch. 6 - Prob. 60PCh. 6 - What are the products of the following reactions?...Ch. 6 - When 3-methyl-1-butene reacts with HBr, two alkyl...Ch. 6 - Draw curved arrows to show the flow of electrons...Ch. 6 - What reagents are needed to carry out the...Ch. 6 - Prob. 65PCh. 6 - Prob. 66PCh. 6 - Prob. 67PCh. 6 - What is more stable? a. CH3C+HCH3orCH3C+HCH2ClCh. 6 - Prob. 69PCh. 6 - a. Draw the product or products that will be...Ch. 6 - Prob. 71PCh. 6 - The second-order rate constant (in units of M1s1)...Ch. 6 - Which compound has the greater dipole moment?Ch. 6 - Prob. 74PCh. 6 - Prob. 75PCh. 6 - Prob. 76PCh. 6 - Prob. 77PCh. 6 - Prob. 78PCh. 6 - Prob. 79PCh. 6 - Prob. 80PCh. 6 - Prob. 81PCh. 6 - Prob. 82PCh. 6 - Prob. 83PCh. 6 - Prob. 84PCh. 6 - Prob. 85PCh. 6 - Prob. 86PCh. 6 - Draw the products of the following reactions. If...Ch. 6 - Prob. 88PCh. 6 - Prob. 89PCh. 6 - Prob. 90PCh. 6 - Two chemists at Dupont found that lCH2Znl is...Ch. 6 - Prob. 92PCh. 6 - Prob. 93PCh. 6 - What alkene gives the product shown after...Ch. 6 - Prob. 95PCh. 6 - Prob. 96PCh. 6 - Prob. 97PCh. 6 - Prob. 98PCh. 6 - Prob. 99PCh. 6 - Prob. 100PCh. 6 - Propose a mechanism for the following reaction:Ch. 6 - Prob. 102PCh. 6 - Prob. 103P
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