3. The questions below are for compound W, 2,3-dimethyl-1-pentene. a) Draw the structure of compound W. b) Draw the highest energy staggered Newman projection for rotation about the C3 - C4 bond of compound W. c) Use an asterisk (*) to identify the chiral centre of the compound

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3. The questions below are for compound
W, 2,3-dimethyl-1-pentene.
a) Draw the structure of compound W.
b) Draw the highest energy staggered
Newman projection for rotation about the
C3 - C4 bond of compound W.
c) Use an asterisk (*) to identify the chiral
centre of the compound
d) Draw the S-isomer of compound W
e) Give the structure of the MAJOR
product(s) when compound W reacts with
the reagents and conditions below.
Indicate the relative stereochemistry
where relevant
i. Cold concentrated sulfuric acid
ii. Bromine in water
iii.BH3 (borane) followed by H2O2, OH
(alkaline hydrogen peroxide)
f) Provide the mechanism for part e(i) and
the mechanism for e(i). Clearly show all the
steps and intermediates.
Transcribed Image Text:3. The questions below are for compound W, 2,3-dimethyl-1-pentene. a) Draw the structure of compound W. b) Draw the highest energy staggered Newman projection for rotation about the C3 - C4 bond of compound W. c) Use an asterisk (*) to identify the chiral centre of the compound d) Draw the S-isomer of compound W e) Give the structure of the MAJOR product(s) when compound W reacts with the reagents and conditions below. Indicate the relative stereochemistry where relevant i. Cold concentrated sulfuric acid ii. Bromine in water iii.BH3 (borane) followed by H2O2, OH (alkaline hydrogen peroxide) f) Provide the mechanism for part e(i) and the mechanism for e(i). Clearly show all the steps and intermediates.
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