Can someone explain the answers to 28, 29, and 30? The answers are B, A, A. I understand lindar catalyst makes cis alkenes and Na/NH3 makes trans alkenes but I dont understand how the second step of Br2, OsO4 influences the stereochemistry between the 2 . Will rate quickly if helpful. Thanks!

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Can someone explain the answers to 28, 29, and 30? The answers are B, A, A. I understand lindar catalyst makes cis  alkenes and Na/NH3 makes trans alkenes but I dont understand how the second step of Br2, OsO4 influences the stereochemistry between the 2 . Will rate quickly if helpful. Thanks!

complete this synthesis?
-1. What are the of synthesis?
(C) cat. by Br2/CC14
028 What are the best reagents to
(a)
H.
Br
()
Br
H Br
(B) Na/NH3 followed by Br2/CH2C12
(D) Br/CH2C12 followed by H/Pt
(A) 2 HBr
OsO4
Na
NH3
NMO
. What are the products of this synthesis?
H.
HO,
НО Н
HO
(B)
+ enantiomer
H,
()
Но н
+ enantiomer
H.
OH (@)
H.
Et
(C) H
HO
Ме Н
Et.
,
H,
PO-30. What reagents are used in this
synthesis?
HO
H Me
CH3
(B) 1) H2/Lindlar's cat. 2) OsO&/NMO
(D) 1) H2/Lindlar's cat. 2) O3 followed by Me,S
(A) 1) Na/NH3 2) OsO4/NMO
(C) 1) Na/NH3 2) O3 followed by Me2S
Transcribed Image Text:complete this synthesis? -1. What are the of synthesis? (C) cat. by Br2/CC14 028 What are the best reagents to (a) H. Br () Br H Br (B) Na/NH3 followed by Br2/CH2C12 (D) Br/CH2C12 followed by H/Pt (A) 2 HBr OsO4 Na NH3 NMO . What are the products of this synthesis? H. HO, НО Н HO (B) + enantiomer H, () Но н + enantiomer H. OH (@) H. Et (C) H HO Ме Н Et. , H, PO-30. What reagents are used in this synthesis? HO H Me CH3 (B) 1) H2/Lindlar's cat. 2) OsO&/NMO (D) 1) H2/Lindlar's cat. 2) O3 followed by Me,S (A) 1) Na/NH3 2) OsO4/NMO (C) 1) Na/NH3 2) O3 followed by Me2S
Expert Solution
Step 1

Br2/CH2Cl2 always yield two front and back side attack of Br which effect the stereochemistry of the reaction.

The free radical mechanism using Hbr in presence of hv does not effect the stereochemistry of the reaction.

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