Organic Chemistry
Organic Chemistry
7th Edition
ISBN: 9780321803221
Author: Paula Y. Bruice
Publisher: Prentice Hall
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Chapter 4, Problem 73P

(a)

Interpretation Introduction

Interpretation:

The configuration of asymmetric centers in the given compound has to be given.

Concept introduction:

Configurations of Asymmetric centers are assigned by following Cahn-Ingold-Prelog system.

According to Cahn-Ingold-Prelog system,

The group attached to asymmetric center should be ranked based on the atomic number of atom which directly connected to asymmetric center.  The higher the atomic number of atom, higher the priority.  If there is tie, then consider the next atoms attached to the connected atom and so on.

Check the direction of arrow drawn in the direction of decreasing priority.  If the arrow points clockwise direction, then the compound has R configuration.  If the arrow points counterclockwise direction, then the compound has S configuration.  If the group with lowest priority is not bonded by a hatched wedge, then interchange this group (lowest priority) by group bonded to hatched wedge and draw the arrow in priority order but the configuration is assigned as just reverse.

(b)

Interpretation Introduction

Interpretation:

The configuration of asymmetric centers in the given compound has to be drawn.

Concept introduction:

Configurations of Asymmetric centers are assigned by following Cahn-Ingold-Prelog system.

According to Cahn-Ingold-Prelog system,

The group attached to asymmetric center should be ranked based on the atomic number of atom which directly connected to asymmetric center.  The higher the atomic number of atom, higher the priority.  If there is tie, then consider the next atoms attached to the connected atom and so on.

Check the direction of arrow drawn in the direction of decreasing priority.  If the arrow points clockwise direction, then the compound has R configuration.  If the arrow points counterclockwise direction, then the compound has S configuration.  If the group with lowest priority is not bonded by a hatched wedge, then interchange this group (lowest priority) by group bonded to hatched wedge and draw the arrow in priority order but the configuration is assigned as just reverse.

(c)

Interpretation Introduction

Interpretation:

The configuration of asymmetric centers in the given compound has to be determined.

Concept introduction:

Configurations of Asymmetric centers are assigned by following Cahn-Ingold-Prelog system.

According to Cahn-Ingold-Prelog system,

The group attached to asymmetric center should be ranked based on the atomic number of atom which directly connected to asymmetric center.  The higher the atomic number of atom, higher the priority. If there is tie, then consider the next atoms attached to the connected atom and so on.

Check the direction of arrow drawn in the direction of decreasing priority.  If the arrow points clockwise direction, then the compound has R configuration.  If the arrow points counterclockwise direction, then the compound has S configuration.  If the group with lowest priority is not bonded by a hatched wedge, then interchange this group (lowest priority) by group bonded to hatched wedge and draw the arrow in priority order but the configuration is assigned as just reverse.

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Q1: Curved Arrows, Bronsted Acids & Bases, Lewis Acids & Bases Considering the following reactions: a) Predict the products to complete the reactions. b) Use curved electron-pushing arrows to show the mechanism for the reaction in the forward direction. Redraw some of the compounds to explicitly illustrate all bonds that are broken and all bonds that are formed. c) Label Bronsted acids and bases in the left side of the reactions. Label conjugate acids and bases in the right side of the reactions. d) Label Lewis acids and bases, nucleophiles and electrophiles in the left side of the reactions. A. + OH CH30: OH B. + HBr C. H₂SO4 D. CF 3. CH 3 + HCI N H fluoxetine antidepressant 1↓ JDownload
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Chapter 4 Solutions

Organic Chemistry

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