
Organic Chemistry (8th Edition)
8th Edition
ISBN: 9780134042282
Author: Paula Yurkanis Bruice
Publisher: PEARSON
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Chapter 4, Problem 101P
Interpretation Introduction
Interpretation:
The assigning of configuration of each asymmetric center as R if –OH group is on the right and the configuration is S if the –OH is group in on left side for D-glucose has to be checked.
Concept introduction:
- Asymmetric center is a stereocenter which arises to a compound if any atom is bonded to four different groups.
- The stereo-descriptor for other carbohydrates of having more than one chiral center will be evaluated by the location of –OH group (right or left) of farthest chiral carbon from the carbonyl group. Such as,
If the –OH group is located in right side then, the carbohydrate is a D-sugar.
If the –OH group is located in left side then, the carbohydrate is a L-sugar.
- Configuration of a molecule: The configurations of a molecule arise due to the spatial arrangement of atoms. The configuration can be assigned by following CIP rules as follows.
- Assign numbering to the groups which are bonded to the chiral carbon based on the molecular weight and electronegativity.
- If the sequence of the numbering follows clockwise direction the chiral atom is assigned as R configuration.
- If the sequence of the numbering follows anticlockwise direction the chiral atom is assigned as S configuration.
- If the least priority group is on horizontal line in the fisher projection, then configuration is inverted to the obtained configuration from the above CIP rule which means R configuration becomes S and vice versa.
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Rank each of the following substituted benzene molecules in order of which will react fastest (1) to slowest (4) by electrophilic
aromatic substitution.
Explanation
Check
CF3
(Choose one)
OH
(Choose one)
H
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(Choose one)
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Identifying electron-donating and electron-withdrawing effects
For each of the substituted benzene molecules below, determine the inductive and resonance effects the substituent will have on the
benzene ring, as well as the overall electron-density of the ring compared to unsubstituted benzene.
Molecule
Inductive Effects
Resonance Effects
Overall Electron-Density
CF3
O donating
O donating
O electron-rich
O withdrawing
withdrawing
O no inductive effects
O no resonance effects
O electron-deficient
O similar to benzene
OCH3
Explanation
Check
O donating
O donating
○ withdrawing
withdrawing
O no inductive effects
no resonance effects
electron-rich
electron-deficient
O similar to benzene
Х
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Chapter 4 Solutions
Organic Chemistry (8th Edition)
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