Organic Chemistry
Organic Chemistry
7th Edition
ISBN: 9780321803221
Author: Paula Y. Bruice
Publisher: Prentice Hall
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Chapter 3, Problem 71P

(a)

Interpretation Introduction

Interpretation:

The two chair conformers of cis-1-ethyl-3-methylcyclohexane has to be drawn and also the more stable conformer has to be indicated.

Concept introduction:

Conformers: The different spatial arrangements of the atoms that result from rotation about a single bond is called conformational isomers.

Stereoisomerism (or) geometric isomerism: It is known as cis-trans isomerism or E-Z isomerism is a form of stereoisomerism the each of two or more chemical compounds having the same molecular formula but a different geometric arrangement; an unsaturated compound or ring compound in which rotation around a carbon bond is restricted, as in (cis) and (trans) configurations know as geometric isomerism.

Relative stability of cyclohexane: The most stable conformation of cyclohexane is the chair shown to the right, the respective carbon (-C-C-) bonds are it close to (109.50), it is almost free of angle strain, it is also a fully staggered conformation and so is free of torsional strain.  So the chair conformation is the most stable conformation.

(b)

Interpretation Introduction

Interpretation:

The two chair conformers of trans-1-ethyl-2-isopropylcyclohexane has to be drawn.

Concept introduction:

Conformers: The different spatial arrangements of the atoms the result from rotation about a single bond is called conformational isomers.

Stereoisomerism (or) geometric isomerism: It is known as cis-trans isomerism or E-Z isomerism is a form of stereoisomerism the each of two or more chemical compounds having the same molecular formula but a different geometric arrangement; an unsaturated compound or ring compound in which rotation around a carbon bond is restricted, as in (cis) and (trans) configurations know as geometric isomerism.

Relative stability of cyclohexane: The most stable conformation of cyclohexane is the chair shown to the right, the respective carbon (-C-C-) bonds are it close to (109.50), it is almost free of angle strain, it is also a fully staggered conformation and so is free of torsional strain.  So the chair conformation is the most stable conformation.

(c)

Interpretation Introduction

Interpretation:

The two chair conformers of trans-1-ethyl-2-methylcyclohexane has to be drawn and also the more stable conformer has to be indicated.

Concept introduction:

Conformers: The different spatial arrangements of the atoms the result from rotation about a single bond is called conformational isomers.

Stereoisomerism (or) geometric isomerism: It is known as cis-trans isomerism or E-Z isomerism is a form of stereoisomerism the each of two or more chemical compounds having the same molecular formula but a different geometric arrangement; an unsaturated compound or ring compound in which rotation around a carbon bond is restricted, as in (cis) and (trans) configurations know as geometric isomerism.

Relative stability of cyclohexane: The most stable conformation of cyclohexane is the chair shown to the right, the respective carbon (-C-C-) bonds are it close to (109.5°), it is almost free of angle strain, it is also a fully staggered conformation and so is free of torsional strain.  So the chair conformation is the most stable conformation.

(d)

Interpretation Introduction

Interpretation:

The two chair conformers of cis-1,2-diethylcyclohexane has to be drawn.  Also mention the stable one.

Concept introduction:

Conformers: The different spatial arrangements of the atoms the result from rotation about a single bond is called conformational isomers.

Stereoisomerism (or) geometric isomerism: It is known as cis-trans isomerism or E-Z isomerism is a form of stereoisomerism the each of two or more chemical compounds having the same molecular formula but a different geometric arrangement; an unsaturated compound or ring compound in which rotation around a carbon bond is restricted, as in (cis) and (trans) configurations know as geometric isomerism.

Relative stability of cyclohexane: The most stable conformation of cyclohexane is the chair shown to the right, the respective carbon (-C-C-) bonds are it close to (109.50), it is almost free of angle strain, it is also a fully staggered conformation and so is free of torsional strain.  So the chair conformation is the most stable conformation.

(e)

Interpretation Introduction

Interpretation:

The two chair conformers of cis -1-ethyl-3-isopropylcyclohexane has to be drawn.  Also mention the stable one.

Concept introduction:

Conformers: The different spatial arrangements of the atoms the result from rotation about a single bond is called conformational isomers.

Stereoisomerism (or) geometric isomerism: It is known as cis-trans isomerism or E-Z isomerism is a form of stereoisomerism the each of two or more chemical compounds having the same molecular formula but a different geometric arrangement; an unsaturated compound or ring compound in which rotation around a carbon bond is restricted, as in (cis) and (trans) configurations know as geometric isomerism.

Relative stability of cyclohexane: The most stable conformation of cyclohexane is the chair shown to the right, the respective carbon (-C-C-) bonds are it close to (109.50), it is almost free of angle strain, it is also a fully staggered conformation and so is free of torsional strain.  So the chair conformation is the most stable conformation.

(f)

Interpretation Introduction

Interpretation:

The two chair conformers of cis-1-ethyl-4-isopropylcyclohexane has to be drawn.

Concept introduction:

Conformers: The different spatial arrangements of the atoms the result from rotation about a single bond is called conformational isomers.

Stereoisomerism (or) geometric isomerism: It is known as cis-trans isomerism or E-Z isomerism is a form of stereoisomerism the each of two or more chemical compounds having the same molecular formula but a different geometric arrangement; an unsaturated compound or ring compound in which rotation around a carbon bond is restricted, as in (cis) and (trans) configurations know as geometric isomerism.

Relative stability of cyclohexane: The most stable conformation of cyclohexane is the chair shown to the right, the respective carbon (-C-C-) bonds are it close to (109.50), it is almost free of angle strain, it is also a fully staggered conformation and so is free of torsional strain.  So the chair conformation is the most stable conformation.

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Chapter 3 Solutions

Organic Chemistry

Ch. 3.3 - Prob. 15PCh. 3.3 - Prob. 16PCh. 3.3 - What is each compounds systematic name?Ch. 3.4 - Give two names for each of the following alkyl...Ch. 3.4 - Prob. 19PCh. 3.5 - a. What is each ethers systematic name? 1....Ch. 3.6 - Draw the structures of a homologous series of...Ch. 3.6 - Give each of the following a systematic name and...Ch. 3.6 - Prob. 23PCh. 3.6 - Prob. 24PCh. 3.7 - Are the following compounds primary, secondary, or...Ch. 3.7 - Prob. 26PCh. 3.7 - Prob. 27PCh. 3.7 - For each of the following, give the systematic...Ch. 3.8 - Predict the approximate size of the following bond...Ch. 3.9 - Prob. 30PCh. 3.9 - Prob. 31PCh. 3.9 - Prob. 32PCh. 3.9 - Rank the following compounds from highest boiling...Ch. 3.9 - Rank the compounds in each set from highest...Ch. 3.9 - Prob. 35PCh. 3.9 - In which solvent would cyclohexane have the lowest...Ch. 3.10 - a. Draw all the staggered and eclipsed conformers...Ch. 3.10 - Prob. 38PCh. 3.10 - Using Newman projections, draw the most stable...Ch. 3.11 - The bond angles in a regular polygon with n sides...Ch. 3.11 - Prob. 41PCh. 3.11 - Prob. 42PCh. 3.12 - Draw 1,2,3,4,5,6-hexachlorocydohexane with a. all...Ch. 3.13 - The chair conformer of fluorocyclohexane is 0.25...Ch. 3.13 - Using the data in Table 3.9, calculate the...Ch. 3.14 - Prob. 46PCh. 3.14 - Which has a higher percentage of the...Ch. 3.14 - For each of the following disubstituted...Ch. 3.14 - a. Calculate the energy difference between the two...Ch. 3 - a. How many hydrogen does an alkene with 17...Ch. 3 - Draw the structure of octane and isooctaneCh. 3 - Draw a condensed structure and a skeletal...Ch. 3 - Prob. 53PCh. 3 - a. What is each compounds systematic name? b. Draw...Ch. 3 - Which of the following represents a cis isomer?Ch. 3 - a. How many primary carbons does each of the...Ch. 3 - Which of the following conformers of isobutyl...Ch. 3 - Draw a skeletal structure for an alkane that has...Ch. 3 - What is each compounds systematic name? a....Ch. 3 - Which bus a. the higher boiling point:...Ch. 3 - a. Draw Newman projections of the two conformers...Ch. 3 - Ansaid and Motrin belong to the group of drugs...Ch. 3 - Prob. 63PCh. 3 - A student was given the structural formulas of...Ch. 3 - Which of the following conformers has the highest...Ch. 3 - Prob. 66PCh. 3 - Prob. 67PCh. 3 - For rotation about the C-3C-4 bond of...Ch. 3 - Prob. 69PCh. 3 - What is each compounds systematic name? a. b. c....Ch. 3 - Prob. 71PCh. 3 - Why are lower molecular weight alcohols more...Ch. 3 - a. Draw a potential energy diagram for rotation...Ch. 3 - For each of the following compound, determine...Ch. 3 - How many ethers have molecular formula C5H12O?...Ch. 3 - Draw the most stable conformer of the following...Ch. 3 - What is each compounds systematic name?Ch. 3 - Calculate the energy difference between the two...Ch. 3 - The most stable from of glucose (blood sugar) is a...Ch. 3 - Prob. 80PCh. 3 - Explain the following: a. 1-Hexanol has a higher...Ch. 3 - One of the chair conformers of cis-...Ch. 3 - Bromine is a larger atom than chlorine, but the...Ch. 3 - Name the following compounds:Ch. 3 - Prob. 85PCh. 3 - Using the data obtained in Problem 85, calculate...
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