CHEMISTRY (PART TEST)

[TOPIC – ALKYL HALIDES AND ARYL HALIDES]

A MULTIPLE CHOICE QUESTIONS WITH SINGLE ANSWERS:

1. Increasing order of stability among the three main conformations (i.e. eclipse, anti, gauche) or 2-
fluoroethanol is
(a) eclipse, gauche, anti (b) gauche, eclipse, anti
(c) eclipse, anti, gauche (d) anti, gauche, eclipse.

2. Dehydrohalogenation by a strong base is slowest in

The product formed is

(d) No reaction takes place.

Which of the following statements is not correct about the above reaction

(a) Propene is one of the products

(d) in the above mentioned reaction, Grignard reagent does not act as a reducing agent.

5. The correct order of increasing rate of reaction of various nucleophiles towards CH3Br in ethanol is
(a) H2O < Br− < Et3N < EtO− < PhS− (b) H2O < Br− < EtO− < Et3N < PhS−
(c) Br− < H2O < EtO− < Et3N < PhS− (d) H2O < Et3N < Br− < EtO− < PhS−
 which of the following statement is correct for above reactions.
(a) Both X and Y are same molecule

(b) Both (X) and (Y) are same molecule

(c) X is and Y is

(d) X is and Y is

Compound (X) and (Z) are respectively

8. The relative rate of extraction of H and D is 2.6 : 1. The percentage yield of the product A and B in
the following reaction is:

(a) 27.8%, 72.2% (b) 72.2%, 27.8%

(c) 56.52%, 43.48% (d) 43.48%, 56.52%

The product formed is

(c) Racemic mixture

10. What is the relationship between the two structures ?

(a) constitutional isomers

(b) stereoisomers
(c) different drawing of the same conformation of the same compound
(d) different conformations of the same compound

B MULTIPLE CHOICE QUESTIONS WITH MULTIPLE ANSWERS

1. Which of the following will give vinyl chloride

(a) HC ≡ CH + HCl

(b) CH2 = CH2 + Cl2 → + 2KOH (aq) →

(c) CH2 = CH2 + Cl2

(d) ClCH2 – CH2Cl + KOH (alc) (1 mole) →

2. Which of the following represent Williamson synthesis :

(a) C6H5ONa + CH3I → (b)

(c) C6H5ONa + C2H5I → (d)

3. Which of the following reactions are correctly represented.

(a) R – CH = CH2 + HCl →

(b) R – CH = CH2 + HI R – CH2 - CH2 – I

(c) R – CH = CH2 + HBr R – CH2 - CH2 – Br
(d) R – CH = CH2 + HI

4. M – C ≡ CLi + Br – (CH2)8 - Br A B C
X Y
In this reaction, sequences
(a) A is H – C ≡ C – (CH2)8 – Br
(b) B is H–C ≡ C–H and C is LiC≡C–(CH2)8 – Br
(c) B is LiC ≡C-(CH2)8 – Br and

(d) B is LiC ≡ C - (CH)8 – Br and C is Br – (CH2)8 – C ≡ C - (CH2)8 – Br

5. In the Dow process for the manufacture of phenol, chlorobenzene is fused with NaOH at high temp
and under pressure.
 Which of the following statements are correct for above reaction ?
(a) Phenol is formed via an intermediate that is aromatic.
(b) Diphenylether is also formed as by product.
(c) p-phenylphenol is also formed as by product.
(d) Biphenylene is also formed as by-product.

Which of the following statement is/are correct for above reaction.

(a) The product is formed by E2 mechanism
(b) The product is formed by E1CB mechanism
(c) The product is formed by 1, 1-elimination followed by migration of phenyl group.
(d) The intermediate is carbene.

7. The possible product (s) of the following reaction is /are

8. Which of the following statements pertaining to an SN2 reactions are true ?

1. The rate of reaction is independent of the concentration of the nucleophile
2. The nucleophile attacks carbon on the side of the molecule opposite the group being displaced.
3. The reaction proceeds with simultaneous bond formation and bond rupture.
4. Partial racemization of an optically active substrate results.
(a) 1 (b) 2
(c) 3 (d) 4

9. Which of the following compounds give the same carbocation on ionization ?

(a) 1 (b) 4
(c) 2 (d) 3
10. Alkenes X and Y on hydration with dilute H2SO4 give same alcohol Z. Reductive ozonolysis of X
gives P and Q where only Q gives silver mirror test positively. Ozonolysis of Y under similar
conditions gives only R, which is a dicarbonyl compound and gives positive Tollen’s test as well as
iodoform test. The product W of catalytic hydrogenation of X and Y is same which can also be
obtained from reduction of all of the following compounds (1 – 5) by Zn – Cu/C2H5OH.

Which of the following is/are correct informations about the above reactions ?

(b) X and Y are geometrical isomers

C MATCH THE FOLLOWING QUESTIONS

1. Match the column (I) and (II).

Colomn (I) Colomn (II)
(a) CH2 = CH – COOH + HBr (p) Non regioselective
(b) cis CH3 – CH = CH – C2H5 + KMnO4 (q) trans addition
(cold alk.)
(c) cis CH3-CH=CH-CH3 + X2 (r) Primary carbocation
(s) Optically active

2. Match the following

Column I (Substrate) Column II

(Relative rate of solvolysis in 50%
aqueous ethanol at 450C)
(p) 7700

(q) 1

(r) 91

(s) 1,30,000
3. Match the column (I) and (II).
Column I Column II
(a) Carbocations (p) E1
(b) Tetrahedral transition state (q) Nucleophilic-addition
(c) Pentavalent transition state (r)

(d) Carbonyl compounds (s) > C = C < + HX

4. Match the column (I) and (II).

Column I Column II
(a) (CH3)2C = CH2 + HBr (p) 1º carbocation
(q)2º carbocation
(b) + CHBr3 + (CH3)3COK

(r) 3º carbocation

(s) Carbene

5. Match the column (I) and (II).

Column I Column II
(a) Carbocation (p) Reaction with ethylene
(b) Carbanions (q) Reaction with opposite species
(c) Carbenes (r) Rearrangement
(d) Free radicals (s) Disproportionation

6. Match the column (I) and (II).

Column I Column II
(a) (p) 3º > 2º (stability of intermediate)
(b) (q) Rearrangement possible
(c) E1 (r) A less polar solvent favours
(d) E2 (s) Stereospecific

7. Match the column (I) and (II).

(p) Stereoselective
(a)

(b)
(c) cis-2-Butene + Br2
(d) trans-2-Butene + Br2
(q) Stereospecific
(r) Hofmann product
(s) Saytzeff product