Problem 13.34 outlines a general method for the preparation of cis- or trans-disubstituted epoxides. Using that method, identify what reagents you would use to prepare the following epoxide from acetylene: H "Et The transformation above can be performed with some reagent or combination of the reagents listed below. Give the necessary reagent(s) in the correct order, as a string of letters (without spaces or punctuation, such as "EBF"). If there is more than one correct solution, provide just one answer. B D. DMP or PCC H2, Pt EtBr PHCH2BR F H H2SO4, H20, HgsO4 МСРВА (RCO3H) Na, NH3 (/) H2, Lindlar's cat. K TSCI, py PhBr NANH2 1) EtMgBr; 2) H,0+

Organic Chemistry
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Chapter21: Benzene And The Concept Of Aromaticity
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Practice Problem 13.36b
Problem 13.34 outlines a general method for the preparation of cis- or trans-disubstituted epoxides. Using that method, identify what reagents you would use to prepare the
following epoxide from acetylene:
H"
'Et
The transformation above can be performed with some reagent or combination of the reagents listed below. Give the necessary reagent(s) in the correct order, as a string of letters
(without spaces or punctuation, such as "EBF"). If there is more than one correct solution, provide just one answer.
A
B
C
D
DMP or PCC
На, Pt
EtBr
PHCH2BR
E
F
H
H2SO4, H20, HgSO4
МСРВА (RCO3зН)
Na, NH3 (/)
H2, Lindlar's cat.
I
K
TSCI, py
PhBr
NANH2
1) EtMgBr; 2) H30+
Transcribed Image Text:Practice Problem 13.36b Problem 13.34 outlines a general method for the preparation of cis- or trans-disubstituted epoxides. Using that method, identify what reagents you would use to prepare the following epoxide from acetylene: H" 'Et The transformation above can be performed with some reagent or combination of the reagents listed below. Give the necessary reagent(s) in the correct order, as a string of letters (without spaces or punctuation, such as "EBF"). If there is more than one correct solution, provide just one answer. A B C D DMP or PCC На, Pt EtBr PHCH2BR E F H H2SO4, H20, HgSO4 МСРВА (RCO3зН) Na, NH3 (/) H2, Lindlar's cat. I K TSCI, py PhBr NANH2 1) EtMgBr; 2) H30+
Expert Solution
Step 1 Reaction Scheme Outline

General outline for preparation of trans-disubstituted epoxide

Step Reagent used  
Step1

NaNH2 and RCH2Br

R can be phenyl and some other alkyl or aryl Substituent

Acidic Proton abstraction by base and Substitution reaction

Mono substituted terminal Alkyne will form

 

Step 2

NaNH2 and R'Br

R' can be ethyl methyl

Another Acidic Proton of acetylene abstraction by base and Substitution reaction with R'Br

Di substituted  Alkyne will form

Step 3 Na / NH3(l)  Gives Trans alkene
Step4 MCPBA (RCO3H)

trans-disubstituted Epoxide formation

 

General outline for preparation of cis -disubstituted epoxide

Step Reagent used  
Step1

NaNH2 and RCH2Br

R can be phenyl and some other alkyl or aryl Substituent

Acidic Proton abstraction by base and Substitution reaction

Mono substituted terminal Alkyne will form

 

Step 2

NaNH2 and R'Br

R' can be ethyl methyl etc.

Another Acidic Proton of acetylene abstraction by base and Substitution reaction with R'Br

Di substituted  Alkyne will form

Step 3 H2 Lindlar Catalyst  Gives cis alkene 
Step4 MCPBA (RCO3H) Cis-disubstituted Epoxide formation

 

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