Question 3 a) The hydration of compound II gives product III as the major product. Give a mechanism, using curly arrows, to show how product III is formed. CH3 OH CH3 H30* CH;C-CH=CH2 CH;C-CH-CH3 CH3 CH3 II II b) A student was asked to prepare 2 -bromo-2-methylpropane as shown below. CH3 Br-C-CHз ČH3 He went ahead and performed a hydrogen halide addition using 2-methylprop-1-ene using HBr and hydrogen peroxide. He was disappointed when all he got was 1-bromo-2- methylpropane. H3C c=c- H CH3 н-с-сH-Br ČH3 HBr H3C H2O2 2-methylprop-1-ene 1-bromo-2-methylpropane i) Explain clearly what went wrong here and why 2 -bromo-2-methylpropane could not be formed. Use structures and reaction mechanisms to help support your answer. ii) Explain clearly how he can remedy the situation and form the desired product. c) One resonance form of anion C,H,O (J) is drawn below. Draw one other resonance form of C,H,O', and indicate which of the two forms is more stable, explain your choice. H2C=ċ-CH3 (J)

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Question 3
a) The hydration of compound II gives product III as the major product. Give a mechanism,
using curly arrows, to show how product III is formed.
CH3
OH CH3
H30*
CH;C-CH=CH2
CH;C-CH-CH3
CH3
CH3
II
II
b) A student was asked to prepare 2 -bromo-2-methylpropane as shown below.
CH3
Br-C-CHз
ČH3
He went ahead and performed a hydrogen halide addition using 2-methylprop-1-ene using
HBr and hydrogen peroxide. He was disappointed when all he got was 1-bromo-2-
methylpropane.
H3C
c=c-
H
CH3
н-с-сH-Br
ČH3
HBr
H3C
H2O2
2-methylprop-1-ene
1-bromo-2-methylpropane
i) Explain clearly what went wrong here and why 2 -bromo-2-methylpropane could not be
formed. Use structures and reaction mechanisms to help support your answer.
ii) Explain clearly how he can remedy the situation and form the desired product.
c) One resonance form of anion C,H,O (J) is drawn below. Draw one other resonance form
of C,H,O', and indicate which of the two forms is more stable, explain your choice.
H2C=ċ-CH3
(J)
Transcribed Image Text:Question 3 a) The hydration of compound II gives product III as the major product. Give a mechanism, using curly arrows, to show how product III is formed. CH3 OH CH3 H30* CH;C-CH=CH2 CH;C-CH-CH3 CH3 CH3 II II b) A student was asked to prepare 2 -bromo-2-methylpropane as shown below. CH3 Br-C-CHз ČH3 He went ahead and performed a hydrogen halide addition using 2-methylprop-1-ene using HBr and hydrogen peroxide. He was disappointed when all he got was 1-bromo-2- methylpropane. H3C c=c- H CH3 н-с-сH-Br ČH3 HBr H3C H2O2 2-methylprop-1-ene 1-bromo-2-methylpropane i) Explain clearly what went wrong here and why 2 -bromo-2-methylpropane could not be formed. Use structures and reaction mechanisms to help support your answer. ii) Explain clearly how he can remedy the situation and form the desired product. c) One resonance form of anion C,H,O (J) is drawn below. Draw one other resonance form of C,H,O', and indicate which of the two forms is more stable, explain your choice. H2C=ċ-CH3 (J)
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