Organic Chemistry
Organic Chemistry
8th Edition
ISBN: 9781305580350
Author: William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher: Cengage Learning
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Chapter 11, Problem 11.11P

(a)

Interpretation Introduction

Interpretation:

Structural formula for the given name has to be drawn.

Concept Introduction:

Nomenclature of Ether compounds:

The naming of theorganic compound is given by IUPAC (International Union for pure and applied chemistry). In the IUPAC names consist of certain rules for giving chemical names they are,

Ethers are named by selecting the longest carbon chain as the parent alkane and naming the –OR group bonded to it an alkoxy group.

Common name: List the alkyl groups bonded to Oxygen in alphabetical order and adding the word ‘ether’.

Cyclic ether: The presence of Oxygen atom in a saturated ring is indicated by the prefix ox-, and ring sizes from three to six are indicated by the endings –irane, etane, olane, and –ane, respectively.

Numbering of the atoms of the ring begins with the oxygen atom. These compounds and others in which there is a heteroatom (non-carbon atom) in the ring are called heterocycles.

(a)

Expert Solution
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Explanation of Solution

IUPAC name: 2-(1-Methylethoxy)propane

Ethers are named by selecting the longest carbon chain as the parent alkane and naming the –OR group bonded to it an alkoxy group.

Using the above principle, the longest carbon chain is propane (contains three carbons) as the parent alkane; naming the –OR group as alkoxy that is ‘2-(1-methylethoxy).

Therefore, the structure obtained is,

Organic Chemistry, Chapter 11, Problem 11.11P , additional homework tip  1

(b)

Interpretation Introduction

Interpretation:

Structural formula for the given name has to be drawn.

Concept Introduction:

Nomenclature of Ether compounds:

The naming of theorganic compound is given by IUPAC (International Union for pure and applied chemistry). In the IUPAC names consist of certain rules for giving chemical names they are,

Ethers are named by selecting the longest carbon chain as the parent alkane and naming the –OR group bonded to it an alkoxy group.

Common name: List the alkyl groups bonded to Oxygen in alphabetical order and adding the word ‘ether’.

Cyclic ether: The presence of Oxygen atom in a saturated ring is indicated by the prefix ox-, and ring sizes from three to six are indicated by the endings –irane, etane, olane, and –ane, respectively.

Numbering of the atoms of the ring begins with the oxygen atom. These compounds and others in which there is a heteroatom (non-carbon atom) in the ring are called heterocycles.

(b)

Expert Solution
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Explanation of Solution

IUPAC name: trans-2,3-Diethyloxirane

Cyclic ether: The presence of Oxygen atom in a saturated ring is indicated by the prefix ox-, and ring sizes from three to six are indicated by the endings –irane, etane, olane, and –ane, respectively.

Numbering of the atoms of the ring begins with the oxygen atom. These compounds and others in which there is a heteroatom (non-carbon atom) in the ring are called heterocycles.

Using the above principle, the name‘oxirane’ contains two carbons along with one Oxygen atom in a cyclic ringalong with two ‘ethyl’ substituentsin the ring.

Organic Chemistry, Chapter 11, Problem 11.11P , additional homework tip  2

(c)

Interpretation Introduction

Interpretation:

Structural formula for the given name has to be drawn.

Concept Introduction:

Nomenclature of Ether compounds:

The naming of theorganic compound is given by IUPAC (International Union for pure and applied chemistry). In the IUPAC names consist of certain rules for giving chemical names they are,

Ethers are named by selecting the longest carbon chain as the parent alkane and naming the –OR group bonded to it an alkoxy group.

Common name: List the alkyl groups bonded to Oxygen in alphabetical order and adding the word ‘ether’.

Cyclic ether: The presence of Oxygen atom in a saturated ring is indicated by the prefix ox-, and ring sizes from three to six are indicated by the endings –irane, etane, olane, and –ane, respectively.

Numbering of the atoms of the ring begins with the oxygen atom. These compounds and others in which there is a heteroatom (non-carbon atom) in the ring are called heterocycles.

(c)

Expert Solution
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Explanation of Solution

IUPAC name:trans-2-Ethoxycyclopentanol

Ethers are named by selecting the longest carbon chain as the parent alkane and naming the –OR group bonded to it an alkoxy group.

Here, the –OH group is preferred as the first priority and the compound is ‘alcohol’.

In the given compound, the longest carbon chain contains five carbons in a cyclic ring; the parent name is CYCLOPETANE and numbering the parent chain begins with carbon attached to the –OH group located at C-1 and the substituent ‘ethoxy’ is located at C-2.

Therefore, the structure is,

Organic Chemistry, Chapter 11, Problem 11.11P , additional homework tip  3

(d)

Interpretation Introduction

Interpretation:

Structural formula for the given name has to be drawn.

Concept Introduction:

Nomenclature of Ether compounds:

The naming of theorganic compound is given by IUPAC (International Union for pure and applied chemistry). In the IUPAC names consist of certain rules for giving chemical names they are,

Ethers are named by selecting the longest carbon chain as the parent alkane and naming the –OR group bonded to it an alkoxy group.

Common name: List the alkyl groups bonded to Oxygen in alphabetical order and adding the word ‘ether’.

Cyclic ether: The presence of Oxygen atom in a saturated ring is indicated by the prefix ox-, and ring sizes from three to six are indicated by the endings –irane, etane, olane, and –ane, respectively.

Numbering of the atoms of the ring begins with the oxygen atom. These compounds and others in which there is a heteroatom (non-carbon atom) in the ring are called heterocycles.

(d)

Expert Solution
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Explanation of Solution

IUPAC name:Ethenyloxyethene.

Ethers are named by selecting the longest carbon chain as the parent alkane and naming the –OR group bonded to it an alkoxy group.

Using the above principle, the longest carbon chain isethene (contains two carbons with a double bond) as the parent alkene; naming the–OR groups as alkoxy that is Ethenyl.

Organic Chemistry, Chapter 11, Problem 11.11P , additional homework tip  4

(e)

Interpretation Introduction

Interpretation:

Structural formula for the given name has to be drawn.

Concept Introduction:

Nomenclature of Ether compounds:

The naming of theorganic compound is given by IUPAC (International Union for pure and applied chemistry). In the IUPAC names consist of certain rules for giving chemical names they are,

Ethers are named by selecting the longest carbon chain as the parent alkane and naming the –OR group bonded to it an alkoxy group.

Common name: List the alkyl groups bonded to Oxygen in alphabetical order and adding the word ‘ether’.

Cyclic ether: The presence of Oxygen atom in a saturated ring is indicated by the prefix ox-, and ring sizes from three to six are indicated by the endings –irane, etane, olane, and –ane, respectively.

Numbering of the atoms of the ring begins with the oxygen atom. These compounds and others in which there is a heteroatom (non-carbon atom) in the ring are called heterocycles.

(e)

Expert Solution
Check Mark

Explanation of Solution

IUPAC name:Cyclohexene oxide:

Cyclic ether: The presence of Oxygen atom in a saturated ring is indicated by the prefix ox-, and ring sizes from three to six are indicated by the endings –irane, etane, olane, and –ane, respectively.

Numbering of the atoms of the ring begins with the oxygen atom. These compounds and others in which there is a heteroatom (non-carbon atom) in the ring are called heterocycles.

Using the above principle, the longest carbon cyclic ring contains sixcarbon atoms andone Oxygen atom is located at C-1 and 2 as three membered ring.

Organic Chemistry, Chapter 11, Problem 11.11P , additional homework tip  5

(f)

Interpretation Introduction

Interpretation:

Structural formula for the given name has to be drawn.

Concept Introduction:

Nomenclature of Ether compounds:

The naming of theorganic compound is given by IUPAC (International Union for pure and applied chemistry). In the IUPAC names consist of certain rules for giving chemical names they are,

Ethers are named by selecting the longest carbon chain as the parent alkane and naming the –OR group bonded to it an alkoxy group.

Common name: List the alkyl groups bonded to Oxygen in alphabetical order and adding the word ‘ether’.

Cyclic ether: The presence of Oxygen atom in a saturated ring is indicated by the prefix ox-, and ring sizes from three to six are indicated by the endings –irane, etane, olane, and –ane, respectively.

Numbering of the atoms of the ring begins with the oxygen atom. These compounds and others in which there is a heteroatom (non-carbon atom) in the ring are called heterocycles.

(f)

Expert Solution
Check Mark

Explanation of Solution

IUPAC name:3-Cyclopropyloxy-1-propene

Ethers are named by selecting the longest carbon chain as the parent alkane and naming the –OR group bonded to it an alkoxy group.

Using the above principle, the longest carbon chain ispropene (contains three carbons with a double bond) as the parent alkene; naming the–OR groups as alkoxy that is 3-Cyclopropyloxy.

Organic Chemistry, Chapter 11, Problem 11.11P , additional homework tip  6

(g)

Interpretation Introduction

Interpretation:

Structural formula for the given name has to be drawn.

Concept Introduction:

Nomenclature of Ether compounds:

The naming of theorganic compound is given by IUPAC (International Union for pure and applied chemistry). In the IUPAC names consist of certain rules for giving chemical names they are,

Ethers are named by selecting the longest carbon chain as the parent alkane and naming the –OR group bonded to it an alkoxy group.

Common name: List the alkyl groups bonded to Oxygen in alphabetical order and adding the word ‘ether’.

Cyclic ether: The presence of Oxygen atom in a saturated ring is indicated by the prefix ox-, and ring sizes from three to six are indicated by the endings –irane, etane, olane, and –ane, respectively.

Numbering of the atoms of the ring begins with the oxygen atom. These compounds and others in which there is a heteroatom (non-carbon atom) in the ring are called heterocycles.

(g)

Expert Solution
Check Mark

Explanation of Solution

IUPAC name:(R)-2-Methyloxirane

Cyclic ether: The presence of Oxygen atom in a saturated ring is indicated by the prefix ox-, and ring sizes from three to six are indicated by the endings –irane, etane, olane, and –ane, respectively.

Numbering of the atoms of the ring begins with the oxygen atom. These compounds and others in which there is a heteroatom (non-carbon atom) in the ring are called heterocycles.

Using the above principle, the longest three membered cyclic ringscontaintwo carbon atoms and one Oxygen atom and the substituent methyl group is located at C-2.

Organic Chemistry, Chapter 11, Problem 11.11P , additional homework tip  7

(h)

Interpretation Introduction

Interpretation:

Structural formula for the given name has to be drawn.

Concept Introduction:

Nomenclature of Ether compounds:

The naming of theorganic compound is given by IUPAC (International Union for pure and applied chemistry). In the IUPAC names consist of certain rules for giving chemical names they are,

Ethers are named by selecting the longest carbon chain as the parent alkane and naming the –OR group bonded to it an alkoxy group.

Common name: List the alkyl groups bonded to Oxygen in alphabetical order and adding the word ‘ether’.

Cyclic ether: The presence of Oxygen atom in a saturated ring is indicated by the prefix ox-, and ring sizes from three to six are indicated by the endings –irane, etane, olane, and –ane, respectively.

Numbering of the atoms of the ring begins with the oxygen atom. These compounds and others in which there is a heteroatom (non-carbon atom) in the ring are called heterocycles.

(h)

Expert Solution
Check Mark

Explanation of Solution

IUPAC name:1,1-Dimethyloxycyclohexane,

Ethers are named by selecting the longest carbon chain as the parent alkane and naming the –OR group bonded to it an alkoxy group.

Using the above principle, the longest carbon ringiscyclohexane (contains six carbons) as the parent alkane; naming the two–OR groups as alkoxy that bothmethoxy groups located at C-1.

Organic Chemistry, Chapter 11, Problem 11.11P , additional homework tip  8

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Chapter 11 Solutions

Organic Chemistry

Ch. 11.9 - Prob. CQCh. 11.9 - Prob. DQCh. 11 - Write names for these compounds. Where possible,...Ch. 11 - Prob. 11.11PCh. 11 - Each compound given in this problem is a common...Ch. 11 - Account for the fact that tetrahydrofuran (THF) is...Ch. 11 - Prob. 11.14PCh. 11 - Write equations to show a combination of reactants...Ch. 11 - Propose a mechanism for this reaction.Ch. 11 - Prob. 11.17PCh. 11 - Prob. 11.18PCh. 11 - Prob. 11.19PCh. 11 - Prob. 11.20PCh. 11 - Ethylene oxide is the starting material for the...Ch. 11 - Prob. 11.22PCh. 11 - Predict the structural formula of the major...Ch. 11 - The following equation shows the reaction of...Ch. 11 - Propose a mechanism to account for this...Ch. 11 - Acid-catalyzed hydrolysis of the following epoxide...Ch. 11 - Prob. 11.27PCh. 11 - Prob. 11.28PCh. 11 - Prob. 11.29PCh. 11 - Propose a mechanism for the following...Ch. 11 - Show reagents and experimental conditions to...Ch. 11 - Starting with cis-3-hexene, show how to prepare...Ch. 11 - Show reagents to convert cycloheptene to each of...Ch. 11 - Show reagents to convert bromocyclopentane to each...Ch. 11 - Prob. 11.35PCh. 11 - Starting with acetylene and ethylene oxide as the...Ch. 11 - Following are the steps in the industrial...Ch. 11 - Prob. 11.38PCh. 11 - Prob. 11.39PCh. 11 - Aldehydes and ketones react with one molecule of...Ch. 11 - Prob. 11.42PCh. 11 - Write the products of the following sequences of...Ch. 11 - Using your reaction roadmap as a guide, show how...Ch. 11 - Using your reaction roadmap as a guide, show how...Ch. 11 - Using your reaction roadmap as a guide, show how...Ch. 11 - During the synthesis of the antiasthmatic drug...Ch. 11 - Prob. 11.48P
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