John McMurry, Professor Emeritus

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Organic Chemistry

Chapter 23

Organic ChemistryChapter 23

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Problem 23-1

(a)

The structure of 2-ethyl-3-hydroxyhexanal shows a six-carbon chain with aldehyde on the first, ethyl on the second, and hydroxyl group on the third carbon.

(b)

The structure shows a benzene ring attached to the carbonyl carbon that is single-bonded to a methylene group, which single-bonded to a carbon with hydroxyl, methyl, and phenyl groups.

(c)

The structure shows a cyclopentanol single-bonded via C 1 to C 2 of cyclopentanone.

Problem 23-2

The reverse reaction is the exact opposite of the forward reaction shown in Figure 23.2.

Problem 23-3

(a)

The structure shows a cyclopentane ring connected to cyclopentanone through a double bond. The double bond is shared between the first carbon of cyclohexane and the second carbon of cyclopentanone.

(b)

The structure of 1,3-diphenylbut-2-en-1-one shows a four-carbon membered conjugated enone. Two phenyl groups are positioned on the first and third carbon atoms. The second and third carbons are double-bonded.

(c)

The structure of 2-isopropyl-5-methylhex-2-enal shows a six-carbon membered aldehyde with an isopropyl group on the second and methyl group on the third carbon. The second and third carbons are double-bonded.

Problem 23-4

Two structures: methylcyclohexane double-bonded by C 3 to C 5 of 3-methylcyclohexanone, and methylcyclohexane double-bonded by C 3 to C 2 of to 3-methylcyclohexanone.

Problem 23-5

(a)

Not an aldol product

(b)

3-Pentanone

Problem 23-6

1. NaOH; 2. LiAlH₄; 3. H₂/Pd

Problem 23-7

Problem 23-8

(a)

C₆H₅CHO + CH₃COCH₃

(b)

Not easily prepared

(c)

Not easily prepared

Problem 23-9

The CH₂ position between the two carbonyl groups is so acidic that it is completely deprotonated to give a stable enolate ion.

Problem 23-10

Problem 23-11

(a)

The structure of ethyl-2-isopropyl-5-methyl-3-oxohexanoate shows isopropyl and methyl substituents at second and fifth carbon. A carbonyl is positioned on the third carbon with an ethoxy group on the first carbonyl.

(b)

The structure of ethyl-3-oxo-2,4-diphenylbutanoate shows two phenyl groups at second and fourth carbon. Two carbonyl groups are positioned on the first and third carbon, with an ethoxy group on first.

(c)

The structure of ethyl-2,4-dicyclohexyl-3-oxobutanoate shows two cyclohexyl groups at the second and fourth carbon. An ethoxy group is bonded to first carbonyl carbon, and carbonyl is part of third carbon.

Problem 23-12

The cleavage reaction is the exact reverse of the forward reaction.

(a)

(b)

(c)

A four-carbon chain with an ethyl ester on C 1, methyl on C 3, and two acetyl groups (C H 3 C O) on C 4.

Problem 23-17

(a)

Structure of a five-carbon chain with an oxo group on C 2 and two Et O 2 C groups on C 5

(b)

Structure of cyclopentanone ring with the substituents C O O E t and C H 2 C H 2 C double-bonded O C H 3 on C 2.

Problem 23-18

CH₃CH₂COCH

\text{═}

CH₂ + CH₃CH₂NO₂

Problem 23-19

(a)

The structure of cyclopentanone with C H 2 C H 2 C O O E t on second carbon.

(b)

The structure of cyclopentanone with C H 2 C H 2 C H O on second carbon.

(c)

The structure of cyclopentanone in which C 2 is attached to the fourth carbon of pentan-2-one.

Problem 23-20

(a)

Cyclopentanone enamine + propenenitrile

(b)

Cyclohexanone enamine + methyl propenoate

Problem 23-21

2-Cyclohexenone in which C 3 is fused to C 3 of cyclopentanone, C 4 is fused to C 2 of cyclopentanone. C2 of cyclopentanone also has methyl substituent.

Problem 23-22

2,5,5-Trimethyl-1,3-cyclohexanedione + 1-penten-3-one

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- Authors: John McMurry, Professor Emeritus
- Publisher/website: OpenStax
- Book title: Organic Chemistry
- Publication date: Sep 20, 2023
- Location: Houston, Texas
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