John McMurry, Professor Emeritus

Problem 8-1

2-Methyl-2-butene and 2-methyl-1-butene

Problem 8-2

Five

Problem 8-3

trans-1,2-Dichloro-1,2-dimethylcyclohexane

Problem 8-4

First structure has cyclohexane ring with wedge bonded chlorine, dash bonded methyl at C1, and dash bonded methyl at C2. In second structure, wedge and dash bonds interchange at C1.

Problem 8-5

trans-2-Bromocyclopentanol

Problem 8-6

Markovnikov

Problem 8-7

(a)

2-Pentanol

(b)

2-Methyl-2-pentanol

Problem 8-8

(a)

Oxymercuration of 2-methyl-1-hexene or 2-methyl-2-hexene

(b)

Oxymercuration of cyclohexylethylene or hydroboration of ethylidenecyclohexane

Problem 8-9

(a)

The condensed structural formula has a 5-carbon chain. C2 is bonded to a methyl group. C3 is bonded to a hydroxyl group.

(b)

The structure has a cyclohexane ring bonded to a 2-carbon chain with a hydroxyl group bonded to C1 ring attachment.

Problem 8-10

(a)

3-Methyl-1-butene

(b)

2-Methyl-2-butene

(c)

Methylenecyclohexane

Problem 8-11

The first structure has cyclopentane ring with dash-bonded hydroxyl at C1, wedge bonded methyl groups at C2 and C4. In the second structure, one methyl is dash bonded at C4.

Problem 8-12

(a)

2-Methylpentane

(b)

1,1-Dimethylcyclopentane

(c)

tert-Butylcyclohexane

Problem 8-13

Problem 8-14

(a)

1-Methylcyclohexene

(b)

2-Methyl-2-pentene

(c)

1,3-Butadiene

Problem 8-15

(a)

CH₃COCH₂CH₂CH₂CH₂CO₂H

(b)

CH₃COCH₂CH₂CH₂CH₂CHO

Problem 8-16

(a)

2-Methylpropene

(b)

3-Hexene

Problem 8-17

(a)

The structure has a cyclohexane ring fused to C2 of a cyclopropane ring, in which C1 of the cyclopropyl ring is bonded to two chlorine atoms.

(b)

The condensed structure has a 6-carbon chain. C2 and C3 are bonded to a common methylene group. C5 is bonded to a methyl group.

Problem 8-18

(a)

H₂C ═ CHOCH₃

(b)

ClCH ═ CHCl

Problem 8-19

A polymerization reaction shows the formation of ethyl and ethylene chains each with an open single bond that has a wavy chain on it.

Problem 8-20

An optically inactive, non-50 : 50 mixture of two racemic pairs: (2R,4R) + (2S,4S) and (2R,4S) + (2S,4R)

Problem 8-21

Non-50 : 50 mixture of two racemic pairs: (1S,3R) + (1R,3S) and (1S,3S) + (1R,3R)

Chapter 8