Tutorial 12 Solution

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CHEM120 - Tutorial No.

12

1. (a) Provide at least three common regents that can be used to oxidize a secondary alcohol to
a ketone.

(i) CrO3 (ii) PCC (iii) KMnO4 (iv) K2Cr2O7

(b) Provide a suitable alkene that can react with ozone, O3, and dimethyl sulfide, (CH3)2S
to give methanal and propan-2-one as the major products.

Answer:

H CH3 H CH3
O3
(CH3)2S
O + O + (CH3)2S=O
H CH3 H CH3

2-methylpropene methanal propan-2-one dimethyl sulfide

2. (a) Draw the structures for reaction products in the following reactions

F OH F O
(i)
Cl
+ PCC
Cl
Cl Cl OH

OH
O
O
(ii) H3C OH + O
CH3

OH
O
(iii) + H2/Pt CH3
CH3 H3C
H3C

H O
H3C
(iv)
H3C + K2Cr2O7/H2SO4
OH OH

1
O O
(v)
Cl
+ NH2CH2CH3
H3C NHCH2CH3
H3C

(vi) O CH3 OH O
H 2O
+ KOH + K+ O

CH3

CH3
.. ..
NH N
(vii) + H3C Br + HBr

3. Use the Zaitsev’s rule to predict the major and minor product in the following
elimination reaction. Draw and label the structure of major and minor products.

Cl

CH3 CH3CH2O-Na+
H3C

H3C

Ans:
Cl
CH3
H2C
CH3 CH3CH2O-Na+ minor
H3C
H3C
H3C
+
CH3
H3C major
H3C

2
3

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