Organic Chemistry (8th Edition)
Organic Chemistry (8th Edition)
8th Edition
ISBN: 9780134042282
Author: Paula Yurkanis Bruice
Publisher: PEARSON
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Chapter 4, Problem 88P

(a)

Interpretation Introduction

Interpretation:

The possible stereoisomers of the given compound has to be drawn.

Concept introduction:

Stereoisomers are isomers which have different spatial arrangement in spite of same bond connectivity.  Stereoisomers are due to the presence of stereocenter.

Asymmetric center is a stereocenter which arises to hydrocarbons if the carbon is bonded to four different groups.

Fischer projections: the asymmetric center (carbon) represents as the point of intersection of two perpendicular lines, in which the horizontal lines represent the bonds that project out of the plane of the paper and the vertical lines represent the bonds that away from the plane of the paper.

(b)

Interpretation Introduction

Interpretation:

The optically inactive stereoisomers from the above four stereoisomers of the given compound has to be determined.

Concept introduction:

Optical activity of a molecule is the interaction between molecule and plane-polarized light.

Molecule having asymmetric center shows optical activity except mesocompounds.

Asymmetric center is a stereocenter which arises to hydrocarbons if the carbon is bonded to four different groups.

Mesocompounds has asymmetric centers and a plane of symmetry, so the molecule superimposable on its mirror image, thereby the compound is achiral.

If the four groups attached to both asymmetric centers of a compound are identical, then the compound is a mesocompound.

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Chapter 4 Solutions

Organic Chemistry (8th Edition)

Ch. 4.2 - Draw the Z isomer of an alkene that has a CH3 and...Ch. 4.3 - Prob. 13PCh. 4.4 - Prob. 14PCh. 4.5 - Prob. 16PCh. 4.6 - Prob. 17PCh. 4.7 - Prob. 18PCh. 4.8 - Prob. 20PCh. 4.8 - Prob. 22PCh. 4.8 - Prob. 23PCh. 4.8 - Prob. 24PCh. 4.8 - Draw a perspective formula for each or the...Ch. 4.8 - Prob. 27PCh. 4.9 - Prob. 28PCh. 4.9 - What is the configuration of the following...Ch. 4.9 - Prob. 32PCh. 4.10 - Prob. 33PCh. 4.10 - (S)-(+)-Monosodium glutamate (MSG) is a flavor...Ch. 4.11 - Prob. 35PCh. 4.11 - Prob. 36PCh. 4.12 - Prob. 38PCh. 4.12 - Prob. 39PCh. 4.12 - The stereoisomer of cholesterol found in nature is...Ch. 4.12 - Prob. 41PCh. 4.13 - 1-Bromo-2-methylcyclopentane has four pairs of...Ch. 4.13 - Prob. 43PCh. 4.13 - Draw all possible stereoisomers for each of the...Ch. 4.13 - Prob. 45PCh. 4.13 - Of all the possible cyclooctanes that have one...Ch. 4.13 - Prob. 47PCh. 4.13 - Prob. 48PCh. 4.14 - Which of the following compounds has a...Ch. 4.14 - Draw all the stereoisomers for each of the...Ch. 4.15 - Prob. 52PCh. 4.15 - Name the isomers you drew in Problem 52.Ch. 4.15 - Chloramphenicol is a broad-spectrum antibiotic...Ch. 4.15 - Draw a perspective formula for each of the...Ch. 4.15 - Name the following:Ch. 4.15 - Prob. 57PCh. 4.15 - Prob. 59PCh. 4.15 - Convert the perspective formula to a skeletal...Ch. 4.15 - Prob. 62PCh. 4.16 - Prob. 63PCh. 4.17 - Limonene exists as two different stereoisomers....Ch. 4 - a. Draw three constitutional isomers with...Ch. 4 - Prob. 65PCh. 4 - Prob. 66PCh. 4 - Which of the following has an asymmetric center?...Ch. 4 - Prob. 68PCh. 4 - Prob. 69PCh. 4 - Prob. 70PCh. 4 - Prob. 71PCh. 4 - Assign relative priorities to each set of...Ch. 4 - Prob. 73PCh. 4 - Which of the following are optically active?Ch. 4 - Prob. 75PCh. 4 - Name the following:Ch. 4 - Which of the following has an achiral...Ch. 4 - Using skeletal structures, draw the stereoisomers...Ch. 4 - Prob. 79PCh. 4 - Citrate synthase, one of the enzymes in the series...Ch. 4 - Prob. 81PCh. 4 - Prob. 82PCh. 4 - Prob. 83PCh. 4 - Prob. 84PCh. 4 - Prob. 85PCh. 4 - Prob. 86PCh. 4 - Prob. 87PCh. 4 - Prob. 88PCh. 4 - Prob. 89PCh. 4 - a. Draw all the isomers with molecular formula...Ch. 4 - Prob. 91PCh. 4 - Prob. 92PCh. 4 - Draw structures for the following: a....Ch. 4 - For each of the following structures, draw the...Ch. 4 - Prob. 95PCh. 4 - Prob. 96PCh. 4 - Prob. 97PCh. 4 - a. Using the wedge-and-dash notation, draw the...Ch. 4 - Prob. 99PCh. 4 - Prob. 100PCh. 4 - Prob. 101PCh. 4 - a. Draw the two chair conformers for each of the...Ch. 4 - Prob. 103PCh. 4 - Is the following compound optically active?Ch. 4 - Prob. 105P
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