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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Concept explainers

Question
Chapter 2, Problem 2.64P

(a)

Interpretation Introduction

Interpretation:

The conformation of rings A, B, C and D in Cholestanol has to be described.

Concept Introduction:

The conformation structures of six membered rings are given by chair forms.  In the chair conformation, all C-C-C bond angles are 110.90 and the hydrogens on the adjacent carbon atoms are staggered with respect to one another.  In the chair conformation, no two atoms are closely present, so, there is a little strain present in chair conformation structure of cyclohexane.  The C-H bonds in the chair conformation are arranged in axial and equatorial positions.  The bonds that are present parallel to the axis are axial bonds and the bonds that are present perpendicular to the axis are equatorial bonds.  In cyclohexane, six hydrogens are axial and six hydrogens are equatorial.

Organic Chemistry, Chapter 2, Problem 2.64P , additional homework tip  1

(b)

Interpretation Introduction

Interpretation:

The hydroxyl group present on Ring A is either axial or equatorial has to be given.

Concept Introduction:

The C-H bonds in the chair conformation are arranged in axial and equatorial positions.  The bonds that are present parallel to the axis are axial bonds and the bonds that are present perpendicular to the axis are equatorial bonds.  In cyclohexane, six hydrogens are axial and six hydrogens are equatorial.

Organic Chemistry, Chapter 2, Problem 2.64P , additional homework tip  2

(c)

Interpretation Introduction

Interpretation:

The methyl group present at the junction of Ring A and Ring B is either axial or equatorial to Ring A and Ring B has to be given.

Concept Introduction:

The C-H bonds in the chair conformation are arranged in axial and equatorial positions.  The bonds that are present parallel to the axis are axial bonds and the bonds that are present perpendicular to the axis are equatorial bonds.  In cyclohexane, six hydrogens are axial and six hydrogens are equatorial.

Organic Chemistry, Chapter 2, Problem 2.64P , additional homework tip  3

(d)

Interpretation Introduction

Interpretation:

The methyl group present at the junction of Ring C and Ring D is either axial or equatorial has to be given.

Concept Introduction:

The C-H bonds in the chair conformation are arranged in axial and equatorial positions.  The bonds that are present parallel to the axis are axial bonds and the bonds that are present perpendicular to the axis are equatorial bonds.  In cyclohexane, six hydrogens are axial and six hydrogens are equatorial.

Organic Chemistry, Chapter 2, Problem 2.64P , additional homework tip  4

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Chapter 2 Solutions

Organic Chemistry

Ch. 2.5 - Draw a chair conformation of...Ch. 2.6 - Which cycloalkanes show cis, trans isomerism? For...Ch. 2.6 - Following is a planar hexagon representation for...Ch. 2.6 - Here is one cis,trans isomer of...Ch. 2.6 - Prob. AQCh. 2.6 - Prob. BQCh. 2.6 - Prob. CQCh. 2.7 - Arrange the alkanes in each set in order of...Ch. 2 - Write a line-angle formula for each condensed...Ch. 2 - Write the molecular formula of each alkane.Ch. 2 - Using parentheses and subscripts, provide an even...Ch. 2 - Which statements are true about constitutional...Ch. 2 - Prob. 2.20PCh. 2 - Each member of the following set of compounds is...Ch. 2 - Each of the following compounds is an amine...Ch. 2 - Each of the following compounds is either an...Ch. 2 - Draw structural formulas and write IUPAC names for...Ch. 2 - Draw structural formulas for all of the following....Ch. 2 - Write IUPAC names for these alkanes and...Ch. 2 - Write structural formulas and line-angle formulas...Ch. 2 - Explain why each is an incorrect IUPAC name and...Ch. 2 - For each IUPAC name, draw the corresponding...Ch. 2 - Write the IUPAC name for each compound.Ch. 2 - Prob. 2.31PCh. 2 - Torsional strain resulting from eclipsed CH bonds...Ch. 2 - How many different staggered conformations are...Ch. 2 - Consider 1-bromopropane, CH3CH2CH2Br. (a) Draw a...Ch. 2 - Consider 1-bromo-2-methylpropane and draw the...Ch. 2 - trans-1,4-Di-tert-butylcyclohexane exists in a...Ch. 2 - From studies of the dipole moment of...Ch. 2 - Prob. 2.38PCh. 2 - Following are the alternative chair conformations...Ch. 2 - Prob. 2.40PCh. 2 - Prob. 2.41PCh. 2 - Draw line-angle formulas for the cis and trans...Ch. 2 - Name and draw structural formulas for all...Ch. 2 - Using a planar pentagon representation for the...Ch. 2 - Gibbs free energy differences between...Ch. 2 - Prob. 2.46PCh. 2 - Calculate the difference in Gibbs free energy in...Ch. 2 - Draw the alternative chair conformations for the...Ch. 2 - Use your answers from Problem 2.48 to complete the...Ch. 2 - There are four cis,trans isomers of...Ch. 2 - Draw alternative chair conformations for each...Ch. 2 - 1,2,3,4,5,6-Hexachlorocyclohexane shows cis,trans...Ch. 2 - Prob. 2.53PCh. 2 - What generalization can you make about the...Ch. 2 - What unbranched alkane has about the same boiling...Ch. 2 - Complete and balance the following combustion...Ch. 2 - Following are heats of combustion per mole for...Ch. 2 - Following are structural formulas and heats of...Ch. 2 - Without consulting tables, arrange these compounds...Ch. 2 - Which would you predict to have the larger (more...Ch. 2 - Following are structural formulas for 1,4-dioxane...Ch. 2 - Following is a planar hexagon representation of...Ch. 2 - On the left is a stereorepresentation of glucose...Ch. 2 - Prob. 2.64PCh. 2 - Prob. 2.65P
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