Organic Conversions

Past papers
Madhu
Madhu Haputhanthri
Haputhanthri
Part 3 B.Sc. Hons (Chemistry sp), University of Colombo
B.Sc. Hons (Chemistry
Chemistry sp, sp), University
Graduate of Colombo
Chemist, ICHEM
Chemistry sp, Graduate Chemist, ICHEM

1. a) Show how you would carry out the following synthesis using M as the only organic starting
compound
O
CH3 CH C O CH CH3 CH3 C CH CH CH3
CH3 CH3 CH3 CH3
M

b) i. Show how you would synthesize 2-butanone using acetylene (C2H2) as the only organic staring
compound

ii. Show how you would synthesize the following compound using 2-butanone as one of the starting
compounds
CH3
N C
CH2CH3

(2011 A/L)

Madhu Haputhanthri 1 CHEMISTRY

 2. a) Using only the chemicals given in the list. Show how would carry out the following conversion
O
(CH3)2C CH2 (CH3)3C C O C(CH3)3

List of chemicals
Conc. H2SO4, dil. H2SO4, PCl5, Mg, ether, HCHO, K2Cr2O7

b) Show how you would synthesize the following compound using propanal as the only organic
starting material
O
CH3 CH2 C NH CH2CH2CH3

(2012 A/L)

Madhu Haputhanthri 2 CHEMISTRY

 3. a) Using only the chemicals given in the list, show how you would carry out the following conversion

H3C CH3
CH3 C C H C C List of chemicals
H3C CH3 NaBH4, HgSO4, dil. H2SO4,
conc. H2SO4, PCl5, Mg, ether

b) Show how you would synthesize compound B using compound A as the only organic starting
material
O
O
C
C
NH
Cl

A B

(2013 A/L)

Madhu Haputhanthri 3 CHEMISTRY

 4. a) Using only the chemicals given in the list, show how you would carry out the following conversion

CH CH CH CH3
CHBr CH2Br List of chemicals

H2, Pd/BaSO4/
quinoline, NaBH4, Na,
alcoholic KOH, HgSO4,
dil. H2SO4, PBr3

b) Show how you would synthesize compound B using compound A as the only organic starting
material

CH3CH2OH CH3CHBrCHBrCH3

A B

(2014 A/L)

Madhu Haputhanthri 4 CHEMISTRY

 5. a) Show how the conversion given below could be carried out using only the chemicals given in the
list
OH List of chemicals
C6H6 C6H5 C C2H5
Benzene KMnO4, PBr3, Mg, dry ether,
C2H5
CH3Cl, C2H5OH, anhydrous
AlCl3, conc. H2SO4

b) Show how compound B could be synthesized in less than 7 steps, using compound A as the only
organic starting material

C6H5CH2CONHC6H5 C6H5CH2=N-C6H5

A B

(2015 A/L)

Madhu Haputhanthri 5 CHEMISTRY