ST ANDREWS SCOTS SR SEC SCHOOL

9th Avenue, I.P.Extension, Patparganj, Delhi - 92

WORKSHEET FOR SUMMER VACATION

Class 12 - Chemistry

Section A
1. Complete the following giving the structures of major organic products. [3]
Na Mg

i. A ←−−− C H 3 − (C H3 )2 C − Br −−−−−→ B
ether dry ether
C2 H5 ONa/C2 H5 OH

ii. (C H 3) − (C H3 )2 C − C H2 Br −−−−−−−−−−−−→ C
heat
Anhyd.AlC l3

iii. C
6
H6 + (C H3 ) − (C H3 )2 C − C H − Br −−−−−−−→

2. Classify the following compounds as primary, secondary and tertiary halides. [3]
i. 1-Bromobut-2-ene
ii. 4-Bromopent-2-ene
iii. 2-Bromo-2-methylpropane
3. Out of C6H5CH2Cl and C6H5CHClC6H5 which is more easily hydrolysed by aqueous KOH? [3]
4. Discuss the mechanism of SN1 reaction of haloalkanes. [3]
5. What are ambident nucleophiles? Explain with an example. [3]
6. An aromatic compound (A) having molecular formula C6H6O on treatment with CHCl3 and KOH gives a [3]
mixture two isomers B and C both of B & C give same product D when distilled with Zn dust. Oxidation of D
gives E of formula C7H6O2 The sodium salt of E on heating with soda lime gives F which may also be obtained
by distilling A with zinc dust. Identify compounds A to F giving sequence of reactions.?
7. Draw the structure and name the product formed if the following alcohols are oxidized. Assume that an excess [3]
of oxidizing agent is used.
i. CH3CH2CH2CH2OH
ii. 2-Butanol
iii. 2-methylpropanol
8. Name the reagents which are used in the following conversions: [3]
i. A primary alcohol to an aldehyde
ii. Butan-2-one to butan-2-ol
iii. Phenol to 2, 4, 6-tribromophenol
9. How can phenol be converted to aspirin? [3]
10. Give two reactions that show the acidic nature of phenol. Compare acidity of phenol with that of ethanol. [3]
Section B
11. Give the IUPAC names of the following compounds: [5]
i. CH3CH(Cl)CH(Br)CH3

ii. CHF2CBrClF

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 iii. ClCH2C = CCH2Br

iv. (CCl3)3CCl

v. CH3C(p - ClC6H4)2CH(Br)CH3
vi. (CH3)3CCH = CCl(p - C6H4I)

12. Among the isomeric alkanes of molecular formula C5H12, identify the one that on photochemical chlorination [5]

yields
i. A single monochloride.
ii. Three isomeric monochlorides.
iii. Four isomeric monochlorides.
13. Outline the preparation of the following compounds using a nucleophilic substitution reaction: [5]
i. C H 3 OC (C H3 )3

ii. C H 3 C H2 C H2 N (C H3 )2

iii. C H 3 C H2 C H2 C H2 N O2

iv. C6 H5 C H2 N
+
= C
−

v. C H 3 C H2 C   −  C   ≡  C H2 C H3

vi. C6 H5 C H2 OC OC H3

vii. C H 3 C H2 C H2 C N

viii. C H 3 C H2 −  O  −  N   =  O

14. i. Which compound in each of the following pairs will react faster towards SN2 reaction with-OH group? [5]

a. CH3Br or CH3I

b. (CH3)3C-Cl or CH3-Cl

ii. Write the product(s) of the following reactions.

a. CH3-Cl+KCN→?

b.

15. Give the uses of freon 12, DDT, carbon tetrachloride and iodoform. [5]
16. a. Account for the following : [5]

i. O-nitrophenol is more steam volatile than P-nitrophenol.

ii. t-butyl chloride on heating with sodium methoxide gives 2-methylpropene instead of t-butymethylether.
b. Write the reaction involved in the following :
i. Reimer-Tiemann reaction
c. Give simple chemical test to distinguish between Ethanol and Phenol.

17. a. How do you convert the following: [5]

i. Phenol to Anisole
ii. Ethanol to Propan-2-ol
b. Write mechanism of the following reaction:

H2 SO4
C2 H5 OH CH2 = CH2 + H2 O
443K

c. why phenol undergoes electrophilic substitution more easily than benzene?

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18. Give structures of the products you would expect when each of the following alcohol reacts with (a) HCl -ZnCl2 [5]
HBr and SOCl2.

i. Butan-1-ol
ii. 2-Methylbutan-2-ol
19. Ortho and para nitrophenols are more acidic than phenol. Draw the resonance structures of the corresponding [5]
phenoxide ions.
20. Alcohols react with active metals e.g. Na, K, etc. to give corresponding alkoxides. Write down the decreasing [5]
order of reactivity of sodium metal towards primary, secondary, and tertiary alcohols.

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