Reaction (i) Me HBr Reaction (ii) H202 H20 H BH3 он Me. Me Me 1 equivalent 1 equivalent Ме NaOH Me Br Он unexpected major product intermediate X

Chemistry
10th Edition
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
Section: Chapter Questions
Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
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 Organic chemistry student Everett has set up two separate electrophilic addition 
reactions with 2-butyne (shown below). In reaction (i) the alkyne is treated with 1 equivalent of 
HBr, which successful provides (Z)-2-bromo-2-butene. In reaction (ii) the alkyne is subjected to a 
two-step hydroboroation/oxidation sequence. Interestingly, Everett’s second reaction fails to 
provide the desired methyl ketone and instead has provided butan-2,3-diol
(a) Provide the structure of intermediate X form the first step of reaction (ii). 
(b) Briefly explain (use structures if necessary) why reaction (i) provided an alkene where as 
reaction (ii) provided an alkane when only 1 equivalent of the electrophile was used in each 
reaction.  

Reaction (i) Me
HBr
Reaction (ii)
H202
H20
H
BH3
он
Me.
Me
Me 1 equivalent
1 equivalent
Ме
NaOH Me
Br
Он
unexpected
major
product
intermediate X
Transcribed Image Text:Reaction (i) Me HBr Reaction (ii) H202 H20 H BH3 он Me. Me Me 1 equivalent 1 equivalent Ме NaOH Me Br Он unexpected major product intermediate X
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