a) Ethyl 1-ethylpropyl ether Interpretation: The structure of ethyl 1-ethylpropyl ether is to be drawn. Concept introduction: Simple ethers are with no other functional groups are named by identifying the two organic substituents and adding the word ether. If other functional groups are present, the ether part is considered as an alkoxy substituent. To draw: The structure of ethyl 1-ethylpropyl ether.

Question

An unknown hydrocarbon A with the formula C6H12 reacts with 1 molar equivalent ofH2 over a palladium catalyst. Hydrocarbon A also reacts with OsO4 to give diol B. When oxidized with KMnO4 in acidic solution, A gives two fragments. One fragmentis propanoic acid, CH3CH2CO2H, and the other fragment is ketone C. What are thestructures of A, B, and C? Write all reactions and show your reasoning.

Answer 1

Question

Chapter 18.SE, Problem 38AP

Interpretation Introduction

a) Ethyl 1-ethylpropyl ether

Interpretation:

The structure of ethyl 1-ethylpropyl ether is to be drawn.

Concept introduction:

Simple ethers are with no other functional groups are named by identifying the two organic substituents and adding the word ether. If other functional groups are present, the ether part is considered as an alkoxy substituent.

To draw:

The structure of ethyl 1-ethylpropyl ether.

Interpretation Introduction

b) Di (p-chlorophenyl) ether

Interpretation:

The structure of di (p-chlorophenyl) ether is to be drawn.

Concept introduction:

Simple ethers are with no other functional groups are named by identifying the two organic substituents and adding the word ether. If other functional groups are present, the ether part is considered as an alkoxy substituent.

To give:

The structure of di(p-chlorophenyl) ether.

Interpretation Introduction

c) 3, 4-Dimethoxybenzoic acid

Interpretation:

The structure of 3, 4-dimethoxybenzoic acid ether is to be drawn.

Concept introduction:

Simple ethers are with no other functional groups are named by identifying the two organic substituents and adding the word ether. If other functional groups are present, the ether part is considered as an alkoxy substituent.

To give:

The structure of 3, 4-dimethoxybenzoic acid.

Interpretation Introduction

d) Cyclopentyloxycyclohexane

Interpretation:

The structure of cyclopentyloxycyclohexane is to be drawn.

Concept introduction:

Simple ethers are with no other functional groups are named by identifying the two organic substituents and adding the word ether. If other functional groups are present, the ether part is considered as an alkoxy substituent.

To give:

The structure of cyclopentyloxycyclohexane.

Interpretation Introduction

e) 4-Allyl-2-methoxyphenol (eugenol)

Interpretation:

The structure of 4-allyl-2-methoxyphenol (eugenol) is to be drawn.

Concept introduction:

Simple ethers are with no other functional groups are named by identifying the two organic substituents and adding the word ether. If other functional groups are present, the ether part is considered as an alkoxy substituent.

To give:

The structure of 4-allyl-2-methoxyphenol (eugenol).

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An unknown hydrocarbon A with the formula C6H12 reacts with 1 molar equivalent ofH2 over a palladium catalyst. Hydrocarbon A also reacts with OsO4 to give diol B. When oxidized with KMnO4 in acidic solution, A gives two fragments. One fragmentis propanoic acid, CH3CH2CO2H, and the other fragment is ketone C. What are thestructures of A, B, and C? Write all reactions and show your reasoning.

Acid-catalyzed hydration of 2-Methyl-1-butene yields two alcohols. The major product does not undergo oxidation, while the minor product will undergo oxidation. Explain why, by showing the structures of theproducts.

An unknown hydrocarbon A with the formula C6H12 reacts with 1 molar equivalent of H2 over a palladium catalyst to give hydrocarbon B. Hydrocarbon A also reacts with OsO4 to give the glycol C. When oxidized with KMnO4 in acidic solution, A gives two fragments. One fragment is propanoic acid, CH3CH2COOH, and the other fragment is ketone D (R2C=O). What are the structures of A, B, C and D? Write all reactions.

Answer 2

Question

Chapter 18.SE, Problem 38AP

Interpretation Introduction

a) Ethyl 1-ethylpropyl ether

Interpretation:

The structure of ethyl 1-ethylpropyl ether is to be drawn.

Concept introduction:

Simple ethers are with no other functional groups are named by identifying the two organic substituents and adding the word ether. If other functional groups are present, the ether part is considered as an alkoxy substituent.

To draw:

The structure of ethyl 1-ethylpropyl ether.

Interpretation Introduction

b) Di (p-chlorophenyl) ether

Interpretation:

The structure of di (p-chlorophenyl) ether is to be drawn.

Concept introduction:

Simple ethers are with no other functional groups are named by identifying the two organic substituents and adding the word ether. If other functional groups are present, the ether part is considered as an alkoxy substituent.

To give:

The structure of di(p-chlorophenyl) ether.

Interpretation Introduction

c) 3, 4-Dimethoxybenzoic acid

Interpretation:

The structure of 3, 4-dimethoxybenzoic acid ether is to be drawn.

Concept introduction:

Simple ethers are with no other functional groups are named by identifying the two organic substituents and adding the word ether. If other functional groups are present, the ether part is considered as an alkoxy substituent.

To give:

The structure of 3, 4-dimethoxybenzoic acid.

Interpretation Introduction

d) Cyclopentyloxycyclohexane

Interpretation:

The structure of cyclopentyloxycyclohexane is to be drawn.

Concept introduction:

Simple ethers are with no other functional groups are named by identifying the two organic substituents and adding the word ether. If other functional groups are present, the ether part is considered as an alkoxy substituent.

To give:

The structure of cyclopentyloxycyclohexane.

Interpretation Introduction

e) 4-Allyl-2-methoxyphenol (eugenol)

Interpretation:

The structure of 4-allyl-2-methoxyphenol (eugenol) is to be drawn.

Concept introduction:

Simple ethers are with no other functional groups are named by identifying the two organic substituents and adding the word ether. If other functional groups are present, the ether part is considered as an alkoxy substituent.

To give:

The structure of 4-allyl-2-methoxyphenol (eugenol).

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Answer 3

Question

Chapter 18.SE, Problem 38AP

Interpretation Introduction

a) Ethyl 1-ethylpropyl ether

Interpretation:

The structure of ethyl 1-ethylpropyl ether is to be drawn.

Concept introduction:

Simple ethers are with no other functional groups are named by identifying the two organic substituents and adding the word ether. If other functional groups are present, the ether part is considered as an alkoxy substituent.

To draw:

The structure of ethyl 1-ethylpropyl ether.

Interpretation Introduction

b) Di (p-chlorophenyl) ether

Interpretation:

The structure of di (p-chlorophenyl) ether is to be drawn.

Concept introduction:

Simple ethers are with no other functional groups are named by identifying the two organic substituents and adding the word ether. If other functional groups are present, the ether part is considered as an alkoxy substituent.

To give:

The structure of di(p-chlorophenyl) ether.

Interpretation Introduction

c) 3, 4-Dimethoxybenzoic acid

Interpretation:

The structure of 3, 4-dimethoxybenzoic acid ether is to be drawn.

Concept introduction:

Simple ethers are with no other functional groups are named by identifying the two organic substituents and adding the word ether. If other functional groups are present, the ether part is considered as an alkoxy substituent.

To give:

The structure of 3, 4-dimethoxybenzoic acid.

Interpretation Introduction

d) Cyclopentyloxycyclohexane

Interpretation:

The structure of cyclopentyloxycyclohexane is to be drawn.

Concept introduction:

Simple ethers are with no other functional groups are named by identifying the two organic substituents and adding the word ether. If other functional groups are present, the ether part is considered as an alkoxy substituent.

To give:

The structure of cyclopentyloxycyclohexane.

Interpretation Introduction

e) 4-Allyl-2-methoxyphenol (eugenol)

Interpretation:

The structure of 4-allyl-2-methoxyphenol (eugenol) is to be drawn.

Concept introduction:

Simple ethers are with no other functional groups are named by identifying the two organic substituents and adding the word ether. If other functional groups are present, the ether part is considered as an alkoxy substituent.

To give:

The structure of 4-allyl-2-methoxyphenol (eugenol).

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Answer 4

Question

Chapter 18.SE, Problem 38AP

Interpretation Introduction

a) Ethyl 1-ethylpropyl ether

Interpretation:

The structure of ethyl 1-ethylpropyl ether is to be drawn.

Concept introduction:

Simple ethers are with no other functional groups are named by identifying the two organic substituents and adding the word ether. If other functional groups are present, the ether part is considered as an alkoxy substituent.

To draw:

The structure of ethyl 1-ethylpropyl ether.

Interpretation Introduction

b) Di (p-chlorophenyl) ether

Interpretation:

The structure of di (p-chlorophenyl) ether is to be drawn.

Concept introduction:

Simple ethers are with no other functional groups are named by identifying the two organic substituents and adding the word ether. If other functional groups are present, the ether part is considered as an alkoxy substituent.

To give:

The structure of di(p-chlorophenyl) ether.

Interpretation Introduction

c) 3, 4-Dimethoxybenzoic acid

Interpretation:

The structure of 3, 4-dimethoxybenzoic acid ether is to be drawn.

Concept introduction:

Simple ethers are with no other functional groups are named by identifying the two organic substituents and adding the word ether. If other functional groups are present, the ether part is considered as an alkoxy substituent.

To give:

The structure of 3, 4-dimethoxybenzoic acid.

Interpretation Introduction

d) Cyclopentyloxycyclohexane

Interpretation:

The structure of cyclopentyloxycyclohexane is to be drawn.

Concept introduction:

Simple ethers are with no other functional groups are named by identifying the two organic substituents and adding the word ether. If other functional groups are present, the ether part is considered as an alkoxy substituent.

To give:

The structure of cyclopentyloxycyclohexane.

Interpretation Introduction

e) 4-Allyl-2-methoxyphenol (eugenol)

Interpretation:

The structure of 4-allyl-2-methoxyphenol (eugenol) is to be drawn.

Concept introduction:

Simple ethers are with no other functional groups are named by identifying the two organic substituents and adding the word ether. If other functional groups are present, the ether part is considered as an alkoxy substituent.

To give:

The structure of 4-allyl-2-methoxyphenol (eugenol).

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Answer 5

Chapter 18.SE, Problem 38AP

Interpretation Introduction

a) Ethyl 1-ethylpropyl ether

Interpretation:

The structure of ethyl 1-ethylpropyl ether is to be drawn.

Concept introduction:

Simple ethers are with no other functional groups are named by identifying the two organic substituents and adding the word ether. If other functional groups are present, the ether part is considered as an alkoxy substituent.

To draw:

The structure of ethyl 1-ethylpropyl ether.

Interpretation Introduction

b) Di (p-chlorophenyl) ether

Interpretation:

The structure of di (p-chlorophenyl) ether is to be drawn.

Concept introduction:

Simple ethers are with no other functional groups are named by identifying the two organic substituents and adding the word ether. If other functional groups are present, the ether part is considered as an alkoxy substituent.

To give:

The structure of di(p-chlorophenyl) ether.

Interpretation Introduction

c) 3, 4-Dimethoxybenzoic acid

Interpretation:

The structure of 3, 4-dimethoxybenzoic acid ether is to be drawn.

Concept introduction:

Simple ethers are with no other functional groups are named by identifying the two organic substituents and adding the word ether. If other functional groups are present, the ether part is considered as an alkoxy substituent.

To give:

The structure of 3, 4-dimethoxybenzoic acid.

Interpretation Introduction

d) Cyclopentyloxycyclohexane

Interpretation:

The structure of cyclopentyloxycyclohexane is to be drawn.

Concept introduction:

Simple ethers are with no other functional groups are named by identifying the two organic substituents and adding the word ether. If other functional groups are present, the ether part is considered as an alkoxy substituent.

To give:

The structure of cyclopentyloxycyclohexane.

Interpretation Introduction

e) 4-Allyl-2-methoxyphenol (eugenol)

Interpretation:

The structure of 4-allyl-2-methoxyphenol (eugenol) is to be drawn.

Concept introduction:

Simple ethers are with no other functional groups are named by identifying the two organic substituents and adding the word ether. If other functional groups are present, the ether part is considered as an alkoxy substituent.

To give:

The structure of 4-allyl-2-methoxyphenol (eugenol).

Answer 6

Chapter 18.SE, Problem 38AP

Interpretation Introduction

a) Ethyl 1-ethylpropyl ether

Interpretation:

The structure of ethyl 1-ethylpropyl ether is to be drawn.

Concept introduction:

Simple ethers are with no other functional groups are named by identifying the two organic substituents and adding the word ether. If other functional groups are present, the ether part is considered as an alkoxy substituent.

To draw:

The structure of ethyl 1-ethylpropyl ether.

Answer 7

Chapter 18.SE, Problem 38AP

Interpretation Introduction

a) Ethyl 1-ethylpropyl ether

Interpretation:

The structure of ethyl 1-ethylpropyl ether is to be drawn.

Concept introduction:

Simple ethers are with no other functional groups are named by identifying the two organic substituents and adding the word ether. If other functional groups are present, the ether part is considered as an alkoxy substituent.

To draw:

The structure of ethyl 1-ethylpropyl ether.

Answer 8

Interpretation Introduction

b) Di (p-chlorophenyl) ether

Interpretation:

The structure of di (p-chlorophenyl) ether is to be drawn.

Concept introduction:

Simple ethers are with no other functional groups are named by identifying the two organic substituents and adding the word ether. If other functional groups are present, the ether part is considered as an alkoxy substituent.

To give:

The structure of di(p-chlorophenyl) ether.

Answer 9

Interpretation Introduction

b) Di (p-chlorophenyl) ether

Interpretation:

The structure of di (p-chlorophenyl) ether is to be drawn.

Concept introduction:

Simple ethers are with no other functional groups are named by identifying the two organic substituents and adding the word ether. If other functional groups are present, the ether part is considered as an alkoxy substituent.

To give:

The structure of di(p-chlorophenyl) ether.

Answer 10

Interpretation Introduction

c) 3, 4-Dimethoxybenzoic acid

Interpretation:

The structure of 3, 4-dimethoxybenzoic acid ether is to be drawn.

Concept introduction:

Simple ethers are with no other functional groups are named by identifying the two organic substituents and adding the word ether. If other functional groups are present, the ether part is considered as an alkoxy substituent.

To give:

The structure of 3, 4-dimethoxybenzoic acid.

Answer 11

Interpretation Introduction

c) 3, 4-Dimethoxybenzoic acid

Interpretation:

The structure of 3, 4-dimethoxybenzoic acid ether is to be drawn.

Concept introduction:

Simple ethers are with no other functional groups are named by identifying the two organic substituents and adding the word ether. If other functional groups are present, the ether part is considered as an alkoxy substituent.

To give:

The structure of 3, 4-dimethoxybenzoic acid.

Answer 12

Interpretation Introduction

d) Cyclopentyloxycyclohexane

Interpretation:

The structure of cyclopentyloxycyclohexane is to be drawn.

Concept introduction:

Simple ethers are with no other functional groups are named by identifying the two organic substituents and adding the word ether. If other functional groups are present, the ether part is considered as an alkoxy substituent.

To give:

The structure of cyclopentyloxycyclohexane.

Answer 13

Interpretation Introduction

d) Cyclopentyloxycyclohexane

Interpretation:

The structure of cyclopentyloxycyclohexane is to be drawn.

Concept introduction:

Simple ethers are with no other functional groups are named by identifying the two organic substituents and adding the word ether. If other functional groups are present, the ether part is considered as an alkoxy substituent.

To give:

The structure of cyclopentyloxycyclohexane.

Answer 14

Interpretation Introduction

e) 4-Allyl-2-methoxyphenol (eugenol)

Interpretation:

The structure of 4-allyl-2-methoxyphenol (eugenol) is to be drawn.

Concept introduction:

Simple ethers are with no other functional groups are named by identifying the two organic substituents and adding the word ether. If other functional groups are present, the ether part is considered as an alkoxy substituent.

To give:

The structure of 4-allyl-2-methoxyphenol (eugenol).

Answer 15

Interpretation Introduction

e) 4-Allyl-2-methoxyphenol (eugenol)

Interpretation:

The structure of 4-allyl-2-methoxyphenol (eugenol) is to be drawn.

Concept introduction:

Simple ethers are with no other functional groups are named by identifying the two organic substituents and adding the word ether. If other functional groups are present, the ether part is considered as an alkoxy substituent.

To give:

The structure of 4-allyl-2-methoxyphenol (eugenol).

Answer 16

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Ch. 18.1 - Name the following ethers:Ch. 18.2 - Why do you suppose only symmetrical ethers are...Ch. 18.2 - How would you prepare the following ethers using a...Ch. 18.2 - Review the mechanism of oxymercuration shown in...Ch. 18.2 - How would you prepare the following ethers? Use...Ch. 18.2 - Prob. 6P Ch. 18.3 - Prob. 7P Ch. 18.3 - Write the mechanism of the acid-induced cleavage...Ch. 18.3 - Why are HI and HBr more effective than HCl in...Ch. 18.4 - What product would you expect from Claisen...

Chapter 18 Solutions