JEE Chemistry Haloalkanes and Haloarenes MCQs Set 26

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Multiple Choice Questions

Question 1: The rate of the SN1 reaction is in the order:
P
Q
R
S
(a) S > Q > R > P
(b) S > R > P > Q
(c) P > Q > R > S
(d) S > R > Q > P
Show Answer & Explanation

Answer: (a) S > Q > R > P

Explanation:
1. SN1 rate follows the stability of the carbocation formed.
2. S gives a secondary benzylic cation, Q a primary benzylic cation, R only a primary alkyl cation, and P (aryl bromide) a phenyl cation that cannot be formed.
3. Order: S > Q > R > P.
4. Answer: (a)

Teacher's Note:
1. Decide first whether the substrate and conditions favour SN1 (stable carbocation, polar protic solvent) or SN2 (unhindered carbon, strong nucleophile, polar aprotic solvent).

Question 2: The product of the reaction of 1-bromo-4-fluorobenzene with Mg in ether is:
(a)
(b)
(c)
(d)
Show Answer & Explanation

Answer: (c)

Explanation:
1. Magnesium inserts into the more reactive C–Br bond; the C–F bond is much stronger and stays unaffected.
2. The product is 4-fluorophenylmagnesium bromide.
3. Answer: (c)

Teacher's Note:
1. Decide first whether the substrate and conditions favour SN1 (stable carbocation, polar protic solvent) or SN2 (unhindered carbon, strong nucleophile, polar aprotic solvent).

Question 3: Toluene on reaction with NBS gives A, which on reaction with KCN/DMF gives B. The product B is:
(a)
(b)
(c)
(d)
Show Answer & Explanation

Answer: (b)

Explanation:
1. NBS brominates the benzylic position (free-radical substitution) to give benzyl bromide (A).
2. KCN in the polar aprotic solvent DMF replaces Br by CN by an SN2 reaction.
3. B is benzyl cyanide (phenylacetonitrile).
4. Answer: (b)

Teacher's Note:
1. Decide first whether the substrate and conditions favour SN1 (stable carbocation, polar protic solvent) or SN2 (unhindered carbon, strong nucleophile, polar aprotic solvent).

Question 4: Ethylene oxide is treated with (i) CH3CH2MgBr, (ii) H3O⁺ to give A, and then with PBr3 to give B. The product B is:
(a)
(b)
(c)
(d)
Show Answer & Explanation

Answer: (c)

Explanation:
1. The Grignard reagent opens the epoxide at the less hindered carbon and adds two carbons: CH3CH2CH2CH2OH after hydrolysis (A, butan-1-ol).
2. PBr3 converts the primary alcohol into the primary bromide.
3. B is 1-bromobutane.
4. Answer: (c)

Teacher's Note:
1. Decide first whether the substrate and conditions favour SN1 (stable carbocation, polar protic solvent) or SN2 (unhindered carbon, strong nucleophile, polar aprotic solvent).

Question 5: In the cumene process, benzene + CH3CH=CH2 (H⁺) gives A, A + O2 gives B, and B with H⁺/H2O gives phenol + acetone. The structure of B is:
(a)
(b)
(c)
(d)
Show Answer & Explanation

Answer: (b)

Explanation:
1. Benzene is alkylated with propene to cumene (A).
2. Air oxidation attacks the tertiary benzylic C–H bond and gives cumene hydroperoxide (B).
3. Acid then rearranges B to phenol and acetone.
4. Answer: (b)

Teacher's Note:
1. Decide first whether the substrate and conditions favour SN1 (stable carbocation, polar protic solvent) or SN2 (unhindered carbon, strong nucleophile, polar aprotic solvent).

Question 6: The end product Q in the sequence benzene → (Cl2/FeCl3) P → (Na/ether) Q is:
(a)
(b)
(c)
(d)
Show Answer & Explanation

Answer: (c)

Explanation:
1. Chlorination of benzene gives chlorobenzene (P).
2. Two molecules of aryl halide couple with sodium in dry ether (Fittig reaction).
3. Q is biphenyl.
4. Answer: (c)

Teacher's Note:
1. Decide first whether the substrate and conditions favour SN1 (stable carbocation, polar protic solvent) or SN2 (unhindered carbon, strong nucleophile, polar aprotic solvent).

Question 7: What is the major product obtained in the reaction of 2-bromobenzyl bromide with NH3 in ethanol?
(a)
(b)
(c)
(d)
Show Answer & Explanation

Answer: (a)

Explanation:
1. The benzylic bromide is reactive towards SN2 and is replaced by NH2.
2. The aryl bromide is unreactive under these conditions.
3. The product is 2-bromobenzylamine.
4. Answer: (a)

Teacher's Note:
1. Decide first whether the substrate and conditions favour SN1 (stable carbocation, polar protic solvent) or SN2 (unhindered carbon, strong nucleophile, polar aprotic solvent).

Question 8: The product of the reaction CH3CH2COOAg + Br2 (heat) is:
(a) CH2=CH2
(b) CH3–CH2–Br
(c) CH3CH2CH2–Br
(d) CH3–CH=CH–CH3
Show Answer & Explanation

Answer: (b) CH3–CH2–Br

Explanation:
1. This is the Hunsdiecker reaction.
2. The silver salt of the acid reacts with bromine to give an alkyl bromide with one carbon fewer (CO2 is lost).
3. Propanoate gives CH3CH2Br.
4. Answer: (b)

Teacher's Note:
1. Decide first whether the substrate and conditions favour SN1 (stable carbocation, polar protic solvent) or SN2 (unhindered carbon, strong nucleophile, polar aprotic solvent).

Question 9: Arrange the following groups in the order of decreasing leaving ability.
A
B
C
D
(a) A > D > B > C
(b) A > D > C > B
(c) A > B > C > D
(d) D > C > B > A
Show Answer & Explanation

Answer: (b) A > D > C > B

Explanation:
1. A good leaving group is the conjugate base of a strong acid.
2. Acid strengths: benzenesulphonic acid > acetic acid > phenol > methanol.
3. Leaving ability: benzenesulphonate (A) > acetate (D) > phenoxide (C) > methoxide (B).
4. Answer: (b)

Teacher's Note:
1. Decide first whether the substrate and conditions favour SN1 (stable carbocation, polar protic solvent) or SN2 (unhindered carbon, strong nucleophile, polar aprotic solvent).

Question 10: The reaction (CH3)2CHCl + NaI in acetone → (CH3)2CHI is known as:
(a) Swarts reaction
(b) Finkelstein reaction
(c) Fittig reaction
(d) Sabatier-Senderens reaction
Show Answer & Explanation

Answer: (b) Finkelstein reaction

Explanation:
1. Halide exchange of an alkyl chloride or bromide with NaI in dry acetone is the Finkelstein reaction.
2. It goes to completion because NaCl or NaBr is insoluble in acetone.
3. Answer: (b)

Teacher's Note:
1. Decide first whether the substrate and conditions favour SN1 (stable carbocation, polar protic solvent) or SN2 (unhindered carbon, strong nucleophile, polar aprotic solvent).

Question 11: Which of the following compounds is the most reactive towards SN2 displacement?
(a) CH3CH2CH2CH2–Cl
(b) (CH3)3C–Cl
(c) CH3–CH(CH3)–CH(Cl)–CH3
(d) (CH3)2CH–CH2–Cl
Show Answer & Explanation

Answer: (a) CH3CH2CH2CH2–Cl

Explanation:
1. SN2 is fastest for unhindered primary halides.
2. 1-Chlorobutane has no branching near the reaction centre.
3. Isobutyl chloride is slowed by the beta branch, the secondary halide is more hindered, and the tertiary halide does not react by SN2.
4. Answer: (a)

Teacher's Note:
1. Decide first whether the substrate and conditions favour SN1 (stable carbocation, polar protic solvent) or SN2 (unhindered carbon, strong nucleophile, polar aprotic solvent).

Question 12: Which of the following statements is incorrect?
(a) The boiling points of alkyl halides follow R–I > R–Br > R–Cl > R–F
(b) Alkyl halides are soluble in organic solvents and less soluble in water
(c) Freons are used as aerosol propellants and in refrigeration and air conditioning
(d) o- and m-Dichlorobenzene have higher melting points than the p-isomer
Show Answer & Explanation

Answer: (d) o- and m-Dichlorobenzene have higher melting points than the p-isomer

Explanation:
1. Boiling points rise with molecular mass and polarisability, which gives statement (a). Alkyl halides cannot hydrogen-bond with water, so (b) is correct, and (c) describes the old uses of freons.
2. The para isomer is symmetrical and packs better in the crystal, so it has the highest melting point; the statement about o- and m-isomers is incorrect.
3. Answer: (d)

Teacher's Note:
1. Decide first whether the substrate and conditions favour SN1 (stable carbocation, polar protic solvent) or SN2 (unhindered carbon, strong nucleophile, polar aprotic solvent).

Question 13: Which one of the following will give a racemised product with C2H5OH?
(a) (CH3)2CH–Br
(b) Ph–C(CH3)2Cl
(c) Ph–CH(CH3)Cl
(d) 1-Bromo-1-methylcyclohexane
Show Answer & Explanation

Answer: (c) Ph–CH(CH3)Cl

Explanation:
1. Racemisation needs an SN1 reaction at a chiral carbon.
2. Ph–CH(CH3)Cl is chiral and forms a stable benzylic carbocation; the planar cation is attacked from both faces to give a racemic mixture.
3. The other halides are achiral.
4. Answer: (c)

Teacher's Note:
1. Decide first whether the substrate and conditions favour SN1 (stable carbocation, polar protic solvent) or SN2 (unhindered carbon, strong nucleophile, polar aprotic solvent).

Question 14: Which of the following molecules would have a carbon-halogen bond most susceptible to nucleophilic substitution?
(a) 2-Fluorobutane
(b) 2-Chlorobutane
(c) 2-Bromobutane
(d) 2-Iodobutane
Show Answer & Explanation

Answer: (d) 2-Iodobutane

Explanation:
1. Among the halogens the C–X bond becomes weaker and X⁻ becomes a better leaving group down the group.
2. The C–I bond is the weakest, so 2-iodobutane reacts most easily.
3. Answer: (d)

Teacher's Note:
1. Decide first whether the substrate and conditions favour SN1 (stable carbocation, polar protic solvent) or SN2 (unhindered carbon, strong nucleophile, polar aprotic solvent).

Question 15: Which of the following is the most reactive towards nucleophilic substitution?
(a) CH2=CH–Cl
(b) C6H5–Cl
(c) CH3–CH=CH–Cl
(d) Cl–CH2–CH=CH2
Show Answer & Explanation

Answer: (d) Cl–CH2–CH=CH2

Explanation:
1. In vinyl chloride, chlorobenzene and 1-chloropropene, the halogen is attached to an sp² carbon and the C–Cl bond is strengthened by resonance.
2. Allyl chloride has an sp³ carbon and gives a resonance-stabilised allylic cation, so it reacts the fastest.
3. Answer: (d)

Teacher's Note:
1. Decide first whether the substrate and conditions favour SN1 (stable carbocation, polar protic solvent) or SN2 (unhindered carbon, strong nucleophile, polar aprotic solvent).

Question 16: An SN2 reaction at an asymmetric carbon of a compound always gives:
(a) An enantiomer of the substrate
(b) A product with opposite rotation
(c) A mixture of diastereomers
(d) A single stereoisomer
Show Answer & Explanation

Answer: (d) A single stereoisomer

Explanation:
1. SN2 is stereospecific, with complete inversion of configuration.
2. It gives one stereoisomer only.
3. The sign of rotation may or may not change, and the product is not always the enantiomer of the substrate, because the nucleophile may differ from the leaving group.
4. Answer: (d)

Teacher's Note:
1. Decide first whether the substrate and conditions favour SN1 (stable carbocation, polar protic solvent) or SN2 (unhindered carbon, strong nucleophile, polar aprotic solvent).

Question 17: The synthesis of an alkyl fluoride is best accomplished by:
(a) Free radical fluorination
(b) Sandmeyer reaction
(c) Finkelstein reaction
(d) Swarts reaction
Show Answer & Explanation

Answer: (d) Swarts reaction

Explanation:
1. Direct fluorination is too violent, and the Finkelstein reaction does not work for fluorides because NaF is not soluble enough.
2. In the Swarts reaction an alkyl chloride or bromide is heated with AgF, Hg2F2, CoF2 or SbF3 to give the alkyl fluoride.
3. Answer: (d)

Teacher's Note:
1. Decide first whether the substrate and conditions favour SN1 (stable carbocation, polar protic solvent) or SN2 (unhindered carbon, strong nucleophile, polar aprotic solvent).

Question 18: The reagent that brings about the conversion of (R)-butan-2-ol to (R)-2-chlorobutane is:
(a) SOCl2
(b) PCl5
(c) PCl3
(d) All of them
Show Answer & Explanation

Answer: (a) SOCl2

Explanation:
1. The configuration is retained.
2. Thionyl chloride in the absence of a base reacts by an SNi mechanism, in which the chloride is delivered from the same face, so the configuration is retained.
3. PCl5 and PCl3 give inversion because chloride attacks from the back (SN2).
4. Answer: (a)

Teacher's Note:
1. Decide first whether the substrate and conditions favour SN1 (stable carbocation, polar protic solvent) or SN2 (unhindered carbon, strong nucleophile, polar aprotic solvent).

Question 19: DDT is manufactured by the acid-catalysed condensation of:
(a) Chloroform and acetone
(b) Chloroform and nitric acid
(c) Chlorobenzene and chloral
(d) Chlorobenzene and chloroform
Show Answer & Explanation

Answer: (c) Chlorobenzene and chloral

Explanation:
1. DDT, 1,1,1-trichloro-2,2-bis(4-chlorophenyl)ethane, is made from two molecules of chlorobenzene and one molecule of chloral (trichloroacetaldehyde) with conc. H2SO4.
2. Answer: (c)

Teacher's Note:
1. Decide first whether the substrate and conditions favour SN1 (stable carbocation, polar protic solvent) or SN2 (unhindered carbon, strong nucleophile, polar aprotic solvent).

Question 20: Which of the following compounds is used as a refrigerant?
(a) Urea
(b) Acrolein
(c) CCl2F2
(d) Ethylene glycol
Show Answer & Explanation

Answer: (c) CCl2F2

Explanation:
1. CCl2F2 (Freon-12, a chlorofluorocarbon) is non-toxic and non-flammable and was widely used as a refrigerant.
2. Ethylene glycol is an antifreeze, not a refrigerant.
3. Answer: (c)

Teacher's Note:
1. Decide first whether the substrate and conditions favour SN1 (stable carbocation, polar protic solvent) or SN2 (unhindered carbon, strong nucleophile, polar aprotic solvent).

Question 21: Which of the following is added to chloroform in a small quantity before it is bottled for sale?
(a) CH3OH
(b) C2H5Cl
(c) C2H5OH
(d) AgNO3
Show Answer & Explanation

Answer: (c) C2H5OH

Explanation:
1. In light and air, chloroform is oxidised to the poisonous phosgene (COCl2).
2. About 1% ethanol is added because it converts phosgene into harmless diethyl carbonate.
3. Answer: (c)

Teacher's Note:
1. Decide first whether the substrate and conditions favour SN1 (stable carbocation, polar protic solvent) or SN2 (unhindered carbon, strong nucleophile, polar aprotic solvent).

Question 22: Arrange the following compounds in order of reactivity towards nucleophilic substitution with HBr.
A
B
C
D
(a) A > B > C > D
(b) C > A > D > B
(c) D > C > B > A
(d) B > D > A > C
Show Answer & Explanation

Answer: (b) C > A > D > B

Explanation:
1. The reaction goes through a benzylic carbocation (SN1), so electron-donating groups on the ring increase the rate.
2. OCH3 is a strong +M donor (C), followed by the unsubstituted ring (A), then Br (D, –I outweighs +M) and then NO2 (B, strongly withdrawing).
3. Order: C > A > D > B.
4. Answer: (b)

Teacher's Note:
1. Decide first whether the substrate and conditions favour SN1 (stable carbocation, polar protic solvent) or SN2 (unhindered carbon, strong nucleophile, polar aprotic solvent).

Question 23: Which of the following is a secondary alkyl halide?
(a) Isobutyl chloride
(b) Isopentyl chloride
(c) Isopropyl chloride
(d) Neopentyl chloride
Show Answer & Explanation

Answer: (c) Isopropyl chloride

Explanation:
1. Isobutyl, isopentyl and neopentyl chloride all have Cl on a CH2 carbon, so they are primary.
2. Isopropyl chloride, (CH3)2CHCl, has Cl on a carbon bonded to two other carbons: secondary.
3. Answer: (c)

Teacher's Note:
1. Decide first whether the substrate and conditions favour SN1 (stable carbocation, polar protic solvent) or SN2 (unhindered carbon, strong nucleophile, polar aprotic solvent).

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