OsO4 H₂O₂ g (viii) T MCPBA CH₂Cl2 b)

Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter30: Orbitals And Organic Chemistry: Pericyclic Reactions
Section30.SE: Something Extra
Problem 40AP
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(vii)
ix
a)
a)
O
c)
OSO4
H₂O₂
D₂
Ni
b)
b)
(viii)
(x)
a)
a)
c)
MCPBA
CH₂Cl2
b)
1) Hg(OAc)2, H₂O
2) NaBH4
c)
b)
Transcribed Image Text:(vii) ix a) a) O c) OSO4 H₂O₂ D₂ Ni b) b) (viii) (x) a) a) c) MCPBA CH₂Cl2 b) 1) Hg(OAc)2, H₂O 2) NaBH4 c) b)
a)
H₂
Pd
C-C
-H and -H
+ A-B
For the following reagents, indicate the following: a) what is added accross the double bond; b) is the addition
stereoselective/stereospecific? If yes, do A and B add syn or anti?; c) draw the product, with relevant
stereochemistry, when the reagent system shown is reacted with 1-methylcyclopentene. The answer to the
first reagent system is shown below.
(i)
b) yes,
syn addition
| |
-C-C-
(achiral, stereochem. not
observable)
| I
A B
(ii)
a)
1) 9-BBN
2) H₂O2, NaOH(aq)
b)
Transcribed Image Text:a) H₂ Pd C-C -H and -H + A-B For the following reagents, indicate the following: a) what is added accross the double bond; b) is the addition stereoselective/stereospecific? If yes, do A and B add syn or anti?; c) draw the product, with relevant stereochemistry, when the reagent system shown is reacted with 1-methylcyclopentene. The answer to the first reagent system is shown below. (i) b) yes, syn addition | | -C-C- (achiral, stereochem. not observable) | I A B (ii) a) 1) 9-BBN 2) H₂O2, NaOH(aq) b)
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