EBK ORGANIC CHEMISTRY
EBK ORGANIC CHEMISTRY
8th Edition
ISBN: 8220102744127
Author: Bruice
Publisher: PEARSON
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Chapter 6, Problem 77P

(a)

Interpretation Introduction

Interpretation:

The products obtained from the reaction of 1-ethylcyclohexene with the given reagents should be determined.

Concept Introduction:

Addition of a hydrogen halide to an alkene:

An alkyl halide is formed, if an hydrogen halide is used as an electrophile in the addition to alkene.

The H+ adds to one of the sp2 carbon and the nucleophile halide ion to other sp2 carbon

The general reaction is represented as:

EBK ORGANIC CHEMISTRY, Chapter 6, Problem 77P , additional homework tip  1

(b)

Interpretation Introduction

Interpretation:

The products obtained from the reaction of 1-ethylcyclohexene with the given reagents should be determined.

Concept Introduction:

H2addition:

Catalytic hydrogenation in presence of Pd/C is an example for syn addition of hydrogen.

EBK ORGANIC CHEMISTRY, Chapter 6, Problem 77P , additional homework tip  2

For cyclic reactants, the addition of H2 will form cis enantiomers since two hydrogens adds to one side of the double bond.

(c)

Interpretation Introduction

Interpretation:

The products obtained from the reaction of 1-ethylcyclohexene with the given reagents should be determined

Concept Introduction:

Hydroboration oxidation:

  • Used to convert an alkene to alcohol.
  • Reagent used is BH3orR2BH
  • Boron is the electrophile which accepts electrons from the alkene and forms bond with one sp2 carbon and give H- to other sp2 carbon.
  • After the addition reaction, an aqueous solution of NaOHandH2O2 is added and OH will be in boron’s place.

(d)

Interpretation Introduction

Interpretation:

The products obtained from the reaction of 1-ethylcyclohexene with the given reagents should be determined

Concept Introduction:

Halogen addition to an alkene:

The addition reaction of halides to alkenes leads to the formation of vicinal dihalide as the product. The two halogens will be on the adjacent carbons.

Mainly Br2andCl2 undergo addition reaction with alkenes and the reaction is carried out in an inert solvent such as dichloromethane.

In general, the reaction can be shown as below.

EBK ORGANIC CHEMISTRY, Chapter 6, Problem 77P , additional homework tip  3

When the bromine approaches the alkene, one bromine accepts the electrons from alkene and give them to the other bromine and a cyclic bromonium ion intermediate is formed.

The formed unstable intermediate reacts with Br- and the product is formed.

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Chapter 6 Solutions

EBK ORGANIC CHEMISTRY

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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