ORGANIC CHEMISTRY
ORGANIC CHEMISTRY
6th Edition
ISBN: 9781260826791
Author: SMITH
Publisher: MCG
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Chapter 4, Problem 75P
Interpretation Introduction

(a)

Interpretation: The axial or equatorial substituents on the rings of the given structure A are to be labeled.

Concept introduction: The different spatial arrangements of atoms that results from the rotation about single bonds are called conformational isomers. The chair conformation of cyclohexane consists of six axial and six equatorial bonds.

The six axial bonds present one on each carbon atom, are parallel and alternate to each other and are in up-down position.

The six equatorial bonds present one on each carbon atom, are present in three sets of two parallel ring bonds. They are in alternate position between the sides around the ring.

Interpretation Introduction

(b)

Interpretation: The skeletal structure of A with the help of wedges and dashed wedges is to be drawn in order to show whether the substituents are located above or below the rings.

Concept introduction: The different spatial arrangements of atoms that results from the rotation about single bonds are called conformational isomers. When two substituents in a conformation are in up or down direction then it is known as cis conformation. But if one substituent is in upward direction and the other is facing down direction, then the conformation is known as trans.

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Chapter 4 Solutions

ORGANIC CHEMISTRY

Ch. 4.5 - Give the IUPAC name for each compound.Ch. 4.5 - Give the structure corresponding to each IUPAC...Ch. 4.8 - Arrange the following compounds in order of...Ch. 4.9 - Problem 4.14 Draw the staggered and eclipsed...Ch. 4.9 - Prob. 15PCh. 4.9 - Prob. 16PCh. 4.10 - Problem 4.17 a. Draw the three staggered and...Ch. 4.10 - Problem 4.18 Rank the following conformations in...Ch. 4.10 - Problem 4.19 Consider rotation around the...Ch. 4.10 - Calculate the destabilization present in each...Ch. 4.12 - Problem 4.21 Classify the ring carbons as up or...Ch. 4.12 - Problem 4.22 Using the cyclohexane with the C’s...Ch. 4.13 - Draw a second chair conformation for each...Ch. 4.13 - Problem 4.24 Draw both conformations for and...Ch. 4.13 - Problem 4.25 Draw the structure for each compound...Ch. 4.13 - Prob. 26PCh. 4.14 - Prob. 31PCh. 4.14 - Prob. 32PCh. 4.15 - Prob. 33PCh. 4 - Name each alkane using the ball-and-stick model,...Ch. 4 - 4.40 Draw the structure corresponding to each...Ch. 4 - 4.42 Give the IUPAC name for each compound. a....Ch. 4 - Prob. 42PCh. 4 - 4.46 Considering rotation around the bond...Ch. 4 - 4.50 Calculate the barrier to rotation for each...Ch. 4 - 4.51 The eclipsed conformation of is less...Ch. 4 - (a) Draw the anti and gauche conformations for...Ch. 4 - For each compound drawn below: a.Label each OH,Br...Ch. 4 - Draw the two possible chair conformations for...Ch. 4 - For each compound drawn below: a. Draw...Ch. 4 - Classify each pair of compounds as constitutional...Ch. 4 - Prob. 66PCh. 4 - 4.64 Draw the products of combustion of each...Ch. 4 - 4.65 Hydrocarbons like benzene are metabolized in...Ch. 4 - Prob. 69PCh. 4 - Prob. 70PCh. 4 - Cyclopropane and cyclobutane have similar strain...Ch. 4 - Prob. 72PCh. 4 - Haloethanes (CH3CH2X,X=Cl,Br,I) have similar...Ch. 4 - Prob. 74PCh. 4 - Prob. 75PCh. 4 - Consider the tricyclic structure B (a) Label each...Ch. 4 - Read Appendix B on naming branched alkyl...Ch. 4 - Read Appendix B on naming bicyclic compounds. Then...
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