The major product of this reaction exists as two stereoisomers. Draw both isomers. Show all hydrogen atoms in the structures. Use wedge and dash bonds to indicate the stereochemistry. You can quickly add condensed hydrogens by clicking the More button and using the +H button. Select Draw Rings More Erase H Br H3C-CH2 H Br-Br H2O H3C CH3 (large еxcess) Feedback electrophilie gttack of broming on tbe doule bond rarul in the

Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Andrei Straumanis
Chapter14: Elimination
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The major product of this reaction exists as two stereoisomers. Draw both isomers.
Show all hydrogen atoms in the structures. Use wedge and dash bonds to indicate the stereochemistry.
You can quickly add condensed hydrogens by clicking the More
button and using the +H button.
Select
Draw
Rings
More
Erase
H
Br
H3C-CH2
H
Br-Br
H20
H3C
CH3
(large
excess)
> Feedback
First, an electrophilic attack of bromine on the double bond results in the
formation of a bromonium ion. Next, a nucleophilic attack of water opens the
bromonium ion ring. The product of the reaction is a halohydrin.
Consider regiochemistry and stcrcochemistry.
1. Will the intermediate ion be more stable with a positive charge on a tertiary
carbon, or on a secondary carbon?
2. Which carbon in the bromonium ring will be attacked by water?
3. In the product, what group is added to the more substituted carbon of the
double bond? To the less substituted carbon?
Do not forget that you nccd to draw two stcrcoisomcrs of the product. Consider
the dircction of brominc attack and later attack by watcr.
Check that you have drawn all hydrogens in the structures. Use wedge and dash
bonds to indicate the stereochemistry of the isomers.
Transcribed Image Text:The major product of this reaction exists as two stereoisomers. Draw both isomers. Show all hydrogen atoms in the structures. Use wedge and dash bonds to indicate the stereochemistry. You can quickly add condensed hydrogens by clicking the More button and using the +H button. Select Draw Rings More Erase H Br H3C-CH2 H Br-Br H20 H3C CH3 (large excess) > Feedback First, an electrophilic attack of bromine on the double bond results in the formation of a bromonium ion. Next, a nucleophilic attack of water opens the bromonium ion ring. The product of the reaction is a halohydrin. Consider regiochemistry and stcrcochemistry. 1. Will the intermediate ion be more stable with a positive charge on a tertiary carbon, or on a secondary carbon? 2. Which carbon in the bromonium ring will be attacked by water? 3. In the product, what group is added to the more substituted carbon of the double bond? To the less substituted carbon? Do not forget that you nccd to draw two stcrcoisomcrs of the product. Consider the dircction of brominc attack and later attack by watcr. Check that you have drawn all hydrogens in the structures. Use wedge and dash bonds to indicate the stereochemistry of the isomers.
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