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ORGANIC CHEMISTRY

1. Multiple choice questions:


[1×10=10]

i) Iodoform can be prepared from all except.

a) isopropyl alcohol b) 3-methyl-2-butanone

c) isobutyl alcohol d) ethyl methyl ketone

ii) In the reaction RX A B, the product B is

a) alkyl chloride b) aldehyde

c) carboxylic acid d) ketone

iii) Phenol reacts with which of the following reagent to give


salicyladehyde?

a) CHCl3 + NaOH b) SiO2 + NaOH

c) CHBr3 + KBrO3 d) KCl + HClO4

iv) The reaction C2H5Ona + C2H5I →C2H5OC2H5 + NaI is known as

a) Kolbe’s synthesis b) Wurtz’s synthesis

c) Williamson’s synthesis d) Grignard’s synthesis

v) Silver mirror test is given by which one of the following compounds?

a) Acetophenone b) Acetone

c) Formaldehyde d) Benzophenone

vi) Which of the following acid reduces Tollens’ reagent?

a) Lactic acid b) Formic acid

c) Acetic acid d) Oxalic acid


vii) Unpleasant smell of carbylamines is obtained when chloroform and
alcoholic KOH are heated with

a) any aromatic amine b) any primary amine

c) any amine d) any aliphatic amine

viii) Which is the monomer of Neoprene in the following:

a) CH2 = CH – CH = CH2 b) CH2 = Ch – C ≡ CH

Cl

c) CH2 = CH – C ≡ CH d) CH2 = C – CH = CH2

CH3

ix) The α – and β – forms of glucose are

a) isomers of D – (+) glucose and L – ( – ) – glucose

b) diastereomers of glucose

c) anomers of glucose

d) isomers which differ in the configuration of C-2

x) Which of the following vitamins is water soluble?

a) Vitamin E b) Vitamin K

c) Vitamin A d) Vitamin B.

2. a) Which one of the following has the highest dipole moment? [1×4=4]
i) CH2Cl2

ii) CHCl3

iii) CCl4

b) Write chemical reaction for the preparation of phenol from


chlorobenzene.

c) Draw the structure of the Hex – 2 – en – 4 – ynoic acid

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d) Name a substance which can be used as an antiseptic as well as
disinfectant.

3. a) Predict the order of reactivity of the following compounds in SN1.


[2×8=16]

C6H5CH2Br, C6H5CH(C6H5) Br, C6H5CH(CH3) Br, C6H5(CH3) (C6H5)Br

OR,

Give the uses of DDT and Iodoform.

b) Write chemical reaction for the preparation of phenol from


chlorobenzene.

OR,

Illustrate with examples the limitations of Williamson synthesis for the


preparation of certain types of ethers.

c) Give simple chemical tests to distinguish between the following pairs


of compounds.

Propanal and Propanone

OR,

Pentan – 2 – one and Pentan – 3 - one

d) Why cannot aromatic primary amines be prepared by Gabriel


phthalimide synthesis?

OR,

Write the reactions of (i) aromatic and (ii) aliphatic primary amines with
nitrous acid.

e) What is the effect of denaturation on the structure of proteins?


OR,

How do you explain the emphotericbehaviour of amino acids?

f) What is tincture of iodine? What is its use?

OR,

Why do soaps not work in hard water?

g) How can you differentiate between addition and condensation


polymerization?

h) Describe cannizaro’s reaction.

4. a) How will you convert the following:


[3×5=15]

i) Aniline to Chlorobenzene

ii) Benzene to diphenyl

OR,

The treatment of alkyl chloride with aqueous KOH leads to the


formation of alcohols but in the presence of alcoholic KOH. Alkenes
are major products. Explain.

b) Explain the following with an example.

i) Williamson ether synthesis

ii) Hofmann’s bromamide reaction

c) Give the structures of A, B & C in the following reactions.

i)

ii)

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OR,

Differentiate between globular and fibrous proteins.

d) How do antiseptics differ from disinfectants? Give one example of each.

e) Define thermoplastics and thermosetting polymers with two examples


of each.

OR,

Write the monomers used for getting the following polymers.

i) Polyvinyl chloride

ii) Teflon

iii) Bakelite

5. a) i) An organic compound with the molecular formula C9H10O forms


2,4-DNP derivative, reduces Tollens’ reagent and
undergoes Cannizzaro reaction. On vigorous oxidation. It
gives 1,2-benzenedicarboxylic acid. Identify the
compound.

ii) An organic compound (A) (molecular formula C8H16O2) was


hydrolysed with dilute sulphuric acid to give a carboxylic
acid (B) and an alcohol (C). Oxidation of (C) with
chromic acid produced (B). (C) on dehydration gives
but – 1 – ene. Write equations for the reactions
involved. [5]

OR,

b) i) An organic compound contains 69.77% carbon, 11.63% hydrogen


and rest oxygen. The molecular mass of the compound is
86. It does not reduce Tollens’ reagent but forms an addition
compound with sodium hydrogensulphite and give positive
iodoform test. On vigorous oxidation it gives ethanoic and
propanoic acid. Write the possible structure of thecompound.

ii) Primary alkyl halide C4H9Br (a) reacted with alcoholic KOH to
give compound (b). Compound (b) is reacted with HBr to
give (c) which is an isomer of (a). When (a) is reacted with
sodium metal it gives compound (d), C8H18 which is different
from the compound formed when n – butyl bromide is
reacted with sodium. Give the structural formula of (a) and write
the equations for all the reactions.

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