The following scheme shows possible interconversions between alkenes, alkyl halides, alcohols and ethers. Study it carefully and answer the questions that follow. (iii) CN (x) (ix) (i) (viii) OH (iv) (vii) Br (V) (vi) OH OH Br он

Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter5: Stereochemistry At Tetrahedral Centers
Section5.SE: Something Extra
Problem 70AP
Question
100%

1. Give a reagent and conditions for step (vi), as well as the detailed reaction mechanism that

explains formation of the depicted product.

 

 

2. Give reagents and conditions for step (viii). Why is the original stereochemistry of the alcohol

retained in the product? Please give a brief explanation (not a reaction mechanism). 

 

3. Give reagents and conditions for step (ix).

 

 

4. Give reagents and conditions for step (x).

 

 

5. Give reagents and conditions that can cleave the ether product of step (viii) and show what

products you will get. Please give a detailed reaction mechanism that explains the outcome

of the reaction.

 

 

6. Draw all the possible stereoisomers of the diol product of step (vi) and assign the

stereochemistry at all chiral centers. In groups of two, designate which stereoisomers are

enantiomers and which ones are diastereomers.

The following scheme shows possible interconversions between alkenes, alkyl halides, alcohols and
ethers. Study it carefully and answer the questions that follow.
(iii)
CN
(x)
(ix)
(i)
(viii)
OH
(iv)
(vii)
Br
(V)
(vi)
OH
OH
Br
он
Transcribed Image Text:The following scheme shows possible interconversions between alkenes, alkyl halides, alcohols and ethers. Study it carefully and answer the questions that follow. (iii) CN (x) (ix) (i) (viii) OH (iv) (vii) Br (V) (vi) OH OH Br он
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