ORGANIC CHEMISTRY TEST

Time : 2 hours F.M=50

I. Choose the correct option: (1×10=10)
1. The order of reactivity of following alcohols with halogen acids is

2. Toluene reacts with a halogen in the presence of iron (III) chloride giving ortho and para
halo compounds. The reaction is
(a) electrophilic elimination reaction
(b) electrophilic substitution reaction
(c) free radical addition reaction
(d) nucleophilic substitution reaction
3. Monochlorination of toluene in sunlight followed by hydrolysis with aq. NaOH yields.
(a) o-Cresol (b) w-Cresol
(c) 2, 4-Dihydroxytoluene (d) Benzyl alcohol
4. Give IUPAC name of the compound given below.

5. Mark the correct order of decreasing acid strength of the following

6. Cannizzaro’s reaction is not given by

7. In Clemmensen reduction carbonyl compound is treated with

(a) zinc amalgam + HCl (b) sodium amalgam + HCl
(c) zinc amalgam + nitric acid (d) sodium amalgam + HNO3
8. Which of the following compounds is most reactive towards nucleophilic addition
reactions?

9. Which of the following is the weakest Bronsted base?

10. The source of nitrogen in Gabriel synthesis of amines is .

(a) sodium azide, NaN3
(b) sodium nitrite, NaNO2
(c) potassium cyanide, KCN
(d) potassium phthalimide, C6H4(CO)2NK
II. Assertion reasoning type: (1×5=5)
a)Both assertion and reason are correct and reason is the correct explanation of assertion.
b) Both assertion and reason are correct and reason isn’t the correct explanation of
assertion.
c) Assertion is correct but reason is incorrect.
d) Assertion is incorrect, but reason is correct
e) Both Assertion and reason are incorrect
1.A:Benzyl alcohol undergoes nucleophilic substitution much more readily than CH3Cl.
R: The intermediate carbocation is less stable in case of CH3Cl.
2.A: 2-pentanol and 3-pentanol cannot be distinguished by iodoform test.
R: Both of them are secondary alcohols.
3.A: Acetaldehyde undergoes aldol condensation with dil. NaOH.
R: Aldehydes without alpha hydrogen undergo aldol condensation.
4. A: The b.p of ethanol is much higher than diethyl ether.
R: Ethanol has intermolecular H-bonding unlike diethyl ether.
5. A: Aniline is a stronger base than ammonia.
R: In aniline, the electron density decreases on Nitrogen due to mesomeric effect.

III. Answer the following: (2×4+3×4+5×3=35)

1. In the following pairs of halogen compounds, which compound undergoes faster
SN1 reaction? (2)

2. A hydrocarbon C5H10 does not react with chlorine in dark but gives a single monochloro
compound C5H9Cl in bright sunlight. Identify the hydrocarbon. (3)
3. Predict the major product of acid catalysed dehydration of 1-methylcyclohexanol and
butan-1-ol. (2)

4. Show how will you synthesise : a)1 -Phenylethanol from a suitable alkene.
b) Cyclohexylmethanol using an alkyl halide by an SN2 reaction.
c)Pentan-1-ol using a suitable alkyl halide. (3)

5. 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. (3)

6. Give simple chemical tests to distinguish between the following pairs of compounds:
Propanal and Propanone & Acetophenone and Benzophenone. (2)

7. Convert : a) 3-Methylaniline into 3-nitrotoluene b) Aniline into 1,3,5-tribromobenzene.

(2)

8. Describe a method for the identification of primary, secondary and tertiary amines. Also
write chemical equations of the reactions involved. (3)

9. Identify A, B, C, D, E, R and R/ in the following: (5)

10. Identify A-D: (5)

11. 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 Tollen’s reagent but forms an
addition compound with sodium hydrogen sulphite and give positive iodoform test. On
vigorous oxidation it gives ethanoic and propanoic acid. Write the possible structure of the
compound. (5)