Ch.

44 Organic Reactions - Supplementary Exercise 2

Section A: Give the major organic product(s) in each of the following reactions.
1.
1. LiAlH4 in dry ether
HOOCCH2COOH
2. H+

2.
CH3CHCH3 HCOOH,
HCOOH, conc.
conc. HH22SO
SO44
heat
OH
3. PCl3
CH3COOH
4.
HCl

5. H2, Pt
CH2=CHCH2CHO
heat

6.
1. LiAlH4 in dry ether
2. H3O+

7. NH3
CH3 C Cl

O
8.
conc. H2SO4
180°C

9.
OH
K2Cr2O7/ H+
HOCH2CH2CCH3
reflux
CH3

10. OH
K2Cr2O7/ H+
HOCH2CH2CHCH3
reflux

11. OH
K2Cr2O7/ H+
HOCH2CH2CHCH3
heat

1
12.
1. LiAlH4 in dry ether

2. H3O+
13. CH3CH2CH2OH
HCOOH
conc. H2SO4, heat

14. O
H2SO4 (aq)
CH3CH2O C CHCH3
heat
CH3

15. CH3C=CHCH3 conc. H3PO4, NaI

CH3 heat

16. Al2O3
CH3CH2CHCH2CH2CH3
heat
OH

17. NaOH (aq)

CH3COOCH2CH2CH3
heat

18. _
cold, dilute KMnO4/ OH
CH3CH=CH2

19. CH3 C NH2 H2SO4 (aq)

O heat
20. H

CH3CH2 C N CH3 H2SO4 (aq)

O heat

21.

conc. , heat

2
22. conc. H2SO4
HO C CH2CH2CH2OH a cyclic product (C4H6O2)
heat
O

23. Na2CO3 (aq)

CH3CH=CHCOOH

24. HO C C OH KOH (aq)

O O
25.
NaOH (aq)

heat

26.
H++
H
reflux

27.
OH-
reflux

28.
H+
HOCH2CH2OH a polymer
heat

Section B
1. Suggest a chemical test to distinguish the following pairs of compounds:
(a) CH3CH2OH and CH3OCH3

(b) CH3CH2OH and CH3COOH

3
 (c) CH3COCH3 and CH3COOH

(d) CH2=CHCH2OH and CH3CH2OH

(e) (CH3)3COH and (CH3)2CHOH

2. Mark each of the following bond angles.

O
CH3

H3C N CH2 O C CHCH3

CH3

3. X is an optically inactive compound with molecular formula C5H12O. When treated with acidified
potassium dichromate, compound Y (C5H10O) is formed as product. Compound Y is resistant to further
oxidation. Deduce the structure of X and Y.

4. X is an optically active compound with molecular formula C5H12O. X reacts with acidified potassium
dichromate to give compound Y (C5H10O2) which reacts with Na2CO3 (aq) to give bubbles of colourless
gas. X can also react with concentrated sulphuric acid to give an optically inactive product, Z. Deduce
the structures of X, Y and Z.