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

Introduction to General, Organic and Biochemistry
11th Edition
ISBN:9781285869759
Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres
Publisher:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres
Chapter7: Reaction Rates And Chemical Equilibrium
Section: Chapter Questions
Problem 7.42P
icon
Related questions
Question

 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
Expert Solution
steps

Step by step

Solved in 4 steps with 4 images

Blurred answer
Knowledge Booster
Rate Laws
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.
Similar questions
  • SEE MORE QUESTIONS
Recommended textbooks for you
Introduction to General, Organic and Biochemistry
Introduction to General, Organic and Biochemistry
Chemistry
ISBN:
9781285869759
Author:
Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres
Publisher:
Cengage Learning
Fundamentals Of Analytical Chemistry
Fundamentals Of Analytical Chemistry
Chemistry
ISBN:
9781285640686
Author:
Skoog
Publisher:
Cengage