10 Haloalkanes and Haloarenes: Solutions

Chapter 10
Haloalkanes and Haloarenes
Solutions
SECTION - A
Objective Type Questions
1. Which of the following is a secondary alkyl halide?

(1) Isobutyl chloride (2) Isopentyl chloride (3) Neopentyl chloride (4) Isopropyl chloride
Sol. Answer (4)
We have Isobutyl chloride

(10) Cl
Isopentyl chloride
Cl
(10)
Neopentyl chloride
Cl
(10)
Isopropyl chloride Cl
(10)
Hence, (4) is a correct option.
2. The IUPAC name of the compound
CH3 CH CH CH2 Br is
(1) 4-Bromobut-2-ene (2) 1-Bromobut-2-ene (3) 3-Bromobut-2-ene (4) Allyl bromide
Sol. Answer (2)
4 3 2 1
CH3 CH CHCH2 Br
IUPAC  1 – Bromobut-2-ene
 (2) is the correct option
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106 Haloalkanes and Haloarenes Solution of Assignment (Set-2)
3. Which of the following may be classified as an aryl halide?
(1) CH2 Cl (2) CH3 CH2 Cl
CH2 CH2 Cl
(3) CH3 Cl (4)
Sol. Answer (3)

The Halide which is in direct linked with Aryl nucleus called Aryl halide.
CH3 Cl
Aryl
ring
 (3) is correct option.
4. Which of the following belongs to the class of vinyl halides?

(1) CH2 CH CHBr CH3 (2) CH3 C CH2
Br
(3) HC C Br (4) CH3 CH CH CH2 Br
Sol. Answer (2)
CH3 C CH2
Br
This is vinyl Halide
C C C
Allylic carbon
Vinylic
Carbon
Double bonded 'C' atoms are vinylic carbon.
therefore Ans is (2).
5. Which one of the following reagents will not convert ethyl alcohol into ethyl chloride?
(1) HCl – ZnCl2 (2) CCl4 (3) PCl5 (4) SOCl2
Sol. Answer (2)
ZnCl2
OH + HCl Cl2 {Lucas reagent}
Very Slow
OH + CCl4 No reaction
OH + PCl5 Cl
SNi
OH + SOCl2 Cl
Mechanism
6. The addition of HBr is easiest with

(1) CH 2 CH Cl (2) Cl CH CH Cl (3) CH 3 CH CH2 (4) (CH3)2C CH2
Solution of Assignment (Set-2) Haloalkanes and Haloarenes 107
Sol. Answer (4)
The reaction of alkine with HBr is basically a kind of electrophilic addition to alkenes in this reaction, a very
first step is a formation of intermediate carbocation which is rate determining step (slow step), followed by
nucleophilic attack.
CH3 CH3 – CH3

+ +
Br
C = CH2 + H C – CH3 CH3
CH3 CH3
(3°)
CH3 Br
(Stable)
Therefore, Ans is (4).
7. CH2 CH NO2 + HBr P ; The major product ‘P’ is

(1) CH2 CH2 NO2 (2) CH3 CH NO2 (3) CH2 C NO2 (4) CH 2 CH Br
Br Br Br
Sol. Answer (1)
CH2 = CH – NO2 + HBr
+
CH2 = CH – NO2 CH2 – CH2 – NO2
+ (Stable)
H –
Br
Br – CH2 – CH2 – NO2
8. The intermediate during the addition of HCl to propene in presence of peroxide is

(1) CH 3 CH CH2 Cl (2) CH3 CH CH3
(3) CH 3 CH 2 CH 2 (4) CH 3 CH 2 CH 2
Sol. Answer (2)
+ – +
+ H Cl
Intermediate
Among all Hx only HBr gives free radical reaction be CO3 with HBr overall process is exothermic. Remaining
Hx (HCl, HF, HI) give ionic reaction.
Br2/heat
9. P; P is
Br
Br Br Br Br
(1) (2) (3) (4)
Br
Sol. Answer (2)
Br2/
This is an example of free radical Halogenation Hence, allylic radical which is most stable will react with Br.
Br
*
Hence, the product is Stability >
order
Resonance stabilised
10. The addition of propene with HOCl proceeds via the addition of
(1) H+ in the first step (2) Cl+ in the first step
(3) OH– in the first step (4) Either H+ or OH– in first step
Sol. Answer (2)
– + + Cl
+ HO Cl
Intermediate
HO  Cl
HOCl Breaks as : HOCl 
And alkene follows electrophilic addition reaction, So at first Cl+ attack.
Here, in a first step the electrophill (Cl+) will attack over the  – e– cloud of alkene leading to electrophillic
addition to alkene.
11. CH3 CH CH2 + HOBr P ; The major product ‘P’ is
Br
(1) CH3 CH CH2 (2) CH3 CH CH2 (3) CH2 CH2 CH2 (4) CH3 C CH3
Br OH OH Br Br OH OH
Sol. Answer (2)
– +
+ Br
+ HO Br
–
OH
OH
Br
HOBr Breaks as
 HO   Br 
HO  Br 
Nu  E 
 
And alkene follows electrolphylic addition reaction. So, Br+ attack at first and then OH attack.
Cl I
12. CH3 CH CH2 P , P is
Cl I
(1) CH3 CH CH2 (2) CH3 CH CH2 (3) CH3 C CH3 (4) CH3 CH2 CH
Cl
I Cl Cl I I
Sol. Answer (2)
+ – +
I
+ I – Cl
Intermediate carbocation
–
Cl
Cl
I
13. Which of the following is correct for the reaction?
HBr
CH3 CH CH2 ?
Peroxide
(1) Electrophilic substitution (2) Anti-Markovnikov’s addition
(3) Nucleophilic substitution (4) Markovnikov’s addition
Sol. Answer (2)
CH3 
CH CH2  
HBr
Peroxide
h
 2ROi
Mechanism R OOR 
ROi  H  Br 
 ROH  Br i
Br
+ Br
H
Br Br
+ H – Br
(Product)
+
Br
Br + Br Br2
(Termination)
Hence, the above product formed reflects Anti-markovnikov's reaction.
CH3
Cl2/hν
14. P ; Product (P) is
CH3 CH3 CH2 Cl CH3

Cl
(1) (2) (3) (4)
Cl
Cl
Sol. Answer (3)
CH3
Cl2/hν Cl
(Free radical Halogenation)
CH3
Br2/hν
15. P (Major), Product (P) is
CH2Br CH3 CH3 CH3

(1) (2) (3) Br (4)
Br Br
Sol. Answer (3)
CH3 CH3 CH3

Br2/h
Br
The reaction occur via free radical pathway and 3° free radical is most stable.
16. Which is most stable radical?
(1) CH3 (2) CH 2 CH CH 2 (3) CH 3 CH 2 (4)
Sol. Answer (2)
Because of resonance allylic radicals are stable.
R
17. Br .
CH2 CH2 Br
The reagent R is
(1) NH3 (2) H2O (3) KCN (4) Na/ether
Sol. Answer (4)
Br R
CH2 – CH2 – Br
The Reagent R would be Na/Dry ether this is actually Wurtz reaction and occurs via free radical mechanism.
18. Which of the following halogen exchange reaction will occur in acetone?
(1) R I + NaCl (2) R F + KCl
(3) R Cl + NaI (4) R F + AgBr
Sol. Answer (3)
R – Cl + NaI  R – I + NaCl
This reaction will occur in acetone because of two reasons :
(i) The reactant NaI is more soluble in acetone.
(ii) Secondly, the formed product NaCl will precipitate out
HNO3
19. + I2 P ; P is
NO2 I I NO2
I
(1) (2) (3) (4)
NO2
Sol. Answer (2)
I
HNO3
+ I2 HNO3 oxidises I2 to I+, so that electrophilic generation becomes easier and hence
the electrophilic aromatic substitution reaction.

This reaction is an example of electrophilic Aromatic substitution.
Br2/FeBr3
20. C6H5CH3 , the reaction is called
(1) Nucleophilic substitution (2) Free radical addition

(3) Electrophilic substitution (4) Free radical substitution
Sol. Answer (3)
CH3 CH3
Br
Br2/FeBr3
CH3 +
Br
 Br   Fe Br4
Br2  FeBr3 
E 

This is electrophilic aromatic substitution.
Cu2Cl2 / HCl
21. C6H5N2Cl , this reaction is named as
(1) Sandmeyer (2) Swarts (3) Wurtz-Fittig (4) Finkelstein

Sol. Answer (1)
+ –
N2 Cl + KI I
This is sandmeyer reaction.
22. Which is most reactive nucleophile in polar protic solvent?

(1) F– (2) Cl– (3) Br– (4) I–
Sol. Answer (4)
I  Br   Cl  F 
(Polar protic medium)
Nucleophilicity
23. Which is most reactive nucleophile in polar aprotic solvent?

(1) F– (2) Cl– (3) Br– (4) I–
Sol. Answer (1)
F   Cl  Br   I
(Polar aprotic medium)
Nucleophilicity
24. Which cannot act as an ambident nucleophile?
(1) CN– (2) NO2− (3) SCN– (4) OH–
Sol. Answer (4)

–
CN
–
NO2 ⇒ These are ambident nucleophile as they two donar site.
–
SCN
Whereas OH has only single site i.e., oxygen atom to donate electron pair.
25. Which of the following solvent is suitable for SN1 reaction?
(1) Non-polar (2) Polar protic (3) Polar aprotic (4) All of these
Sol. Answer (2)
SN1 reaction demands polar protic solvents in order to stabilize the intermediate carbocation.
26. For SN1 mechanism, which of the following is correct?
(1) Inversion (100%) (2) Formation of carbocation
(3) Non-polar solvent (4) Elimination
Sol. Answer (2)
In SN1 mechanism, C+ formation in R.D.S. (Slow step)
27. The reaction,
CH3Br + OH CH3OH + Br
proceeds mainly by the mechanism
(1) SN1 (2) SN2 (3) SE1 (4) SE2
Sol. Answer (2)
CH3Br  OH 
 CH3OH  Br 
This is SN2 reaction.
–
 
HO + H3CBr HO C Br
H H
–
CH3OH + Br
Cl KOH (aq.)
28. CH P.
CH3
Product P (major) is
CH3
(1) H (2) (3) (4) OH
OH OH
Sol. Answer (4)
Cl Ring expansion
CH3 CH3 –
OH (aq.)
OH
(3° Alcohol)
CH3
KOH (alcoholic) HBr/R2O2
29. CH3 C Br (A) (B) , (B) is
∆
(Major)
CH3
CH3 CH3 CH3 CH2 H

(1) CH3 C CH2 Br (2) CH3 C CH3 (3) CH3 C OH (4) CH3 C Br
H Br CH2 Br CH3
Sol. Answer (1)

CH3 CH3
KOH (Alc.)
CH3 C Br  CH3 C CH2
CH3 (A)
HBr / R2O2
CH3
CH3 CH CH2Br
The reaction sequence is basically an elimination reaction followed by Anti-markovnikov's addition.
30. An SN2 reaction at an asymmetric carbon of a compound always gives

(1) An enantiomer of the substrate (2) A product with opposite optical rotation
(3) A mixture of diastereomers (4) A product with 100% inversion
Sol. Answer (4)
SN2 reaction involves 100% inversion.
CH2 OH
+
SOCl2 KCN H
31. (A) (B) (C), the compound (C) is
COOH CH3 CH2 COOH CH3
(1) (2) (3) (4)

COOH
COOH
Sol. Answer (3)
OH Cl CN COOH
+
SOCl2 KCN H
SN2 SN2
(A) (B) (C)
Hence, the product (C) is an acid shown.
32. Which one is the most reactive towards SN1 reaction?
CH3
(1) Ph CH2 Br (2) Ph CH Br (3) Ph CH Br (4) Ph C Br
Ph CH3 Ph
Sol. Answer (4)
CH3
C Br (3° benzylic)
This is most reactive for SN1 reaction amongst the choices given.
CH3 CH3
–
C Br C + Br
(Stabilised in Nature)
[3H, 6R]
Here, 3 Hyperconjugating and 6 Resonating structures are plausible to stabilizers this carbocation.
H aq. KOH H
33. Cl HO
H H
H H
The reaction goes through
(1) SN1 (2) SN2 (3) E2 (4) E1
Sol. Answer (2)
H H
aq.KOH
Cl HO
SN2
H H
H H
34. The order of E2 elimination for alkyl halide is
(1) 1° > 2° > 3° (2) 3° > 2° > 1° (3) 2° > 3° > 1° (4) 3° > 1° > 2°
Sol. Answer (2)
The order of E2 elimination for alkyl halide follows as 3°R – L > 2° R – L > 1° R – L.
Where L = any leaving group.
This is because
(i) In 3° R–L, there is more number of – ‘H’. So, the probablity of attack of base on – ‘H’ is more and
hence E2 reactivity increases.
(ii) Secondly, the transition state of E2 reaction is more stable in case of E2 reaction is more hyperconjugation
with its incipient double bond character and  – ‘H’.
S.O. of Ts of E2 reaction.
L – L – L –
C C R C C H C C H
H R H R H H
– – –
(3° R–L) (2° R–L) (1° R–L)
OH HO HO
(base)
Where L is leaving gp
So, E2 reactivity order 3° R – L > 2° R – > 1° R – L
 
35. 2-Bromopentane is heated with EtO Na in ethanol. The major product obtained is
(1) 2-Ethoxypentane (2) Pent-1-ene (3) Isobutane (4) Pent-2-ene
Sol. Answer (4)
Br H
– +
EtO Na
+

H H H (tans-pent-2ene)
Major
+
Cl
HNO3/H2SO4 NaOH
36. A B ; B is
433 K
NO2 NO2 NO2

OH Cl
(1) (2) (3) (4)
OH
NO2 OH
Sol. Answer (4)
Cl Cl OH
HNO3/H2SO4 NaOH
(EAS) 333
(ArSN)
NO2 NO2
Para Nitrophenol
Cl
Liq. NH3
37. + KNH2 (P). Product (P) is
Cl Cl Cl NH2
NH2
(1) (2) (3) (4)
NH2
NH2
Sol. Answer (4)
Cl NH2
Liq. NH3
+ KNH2
The reaction occurs via benzyne mechanism.
Cl Cl
–
–Cl
H
NH2 NH2
NH3
NH2
NH2
NC
NH2
R
38. ; R is
(1) N2 (2) CHCl3/KOH (alcoholic) (3) NH3 (4) KCN
Sol. Answer (2)
N=C
NH2
R
R must be CHCl3, OH–
Mechanism -
Step Ist :
Cl Cl –
– Cl
H C Cl C Cl
– Cl Cl Cl
OH
C
Cl
Electrophile
(dichloro carbene)
Step IInd : Anilene Vs : CCl2 :
H
+ – H
NH2 + CCl2 N C
Cl
H
Intramolecular
Acid-Base reaction
H
H
N C
Cl
H
+ H
N C
Cl
H
+
–H
H
N C
Cl
+
N C H
–
OH
+ –
N C
or
N C
39. Which of the following acts as a poisonous gas?

(1) COCl2 (2) CCl2F2 (3) Benzene (4) CH3Cl
Sol. Answer (1)
Among the following COCl2 called (Phosgene) is a poisonous gas.
40. Which of the following is used as fire extinguisher under the name pyrene?
(1) CO2 (2) CCl4 (3) CH2 = CH — Cl (4) Cl — CH = CH — Cl
Sol. Answer (2)
CCl4 is right ans, the CCl4 is sold under the name of pyrene.
41. Which of the following is used as a refrigerant?
(1) COCl2 (2) CCl4 (3) CF4 (4) CF2Cl2
Sol. Answer (4)
Dichloro difluoro carbon is used as a refrigerant.
42. Which of the following is known as freon 12?
(1) CHCl3 (2) CCl2F2 (3) Ph-COCH2Cl (4) Ph – Cl
Sol. Answer (2)
Freon 12 is CF2Cl2.
43. (p-ClC6H4)2CHCCl3 is used as a/an
(1) Antiseptic for wounds (2) Insecticide
(3) Pyrene (4) Refrigerant
Sol. Answer (2)
Cl H
Cl C C Cl (DDT) Used as an
insectiside
Cl
Cl
44. CHI3 is used as a/an
(1) Antiseptic for wounds (2) Insecticide
(3) Pyrene (4) Refrigerant
Sol. Answer (1)
CHI3 is called iodoform and is used as antiseptic for wounds.
45. Which one of the following is gem-dihalide?
(1) CH3CHBr2
(2) CH2Br – CH2Br
(3) CH3CHBrCH2Br
(4) CH3CHBrCH2BH2Br Or CH3CHBrCH2B–H2Br Or CH3CHBrCH2CH2Br
Sol. Answer (1)
Incorrect
(i) CH3 – CH2 – Br2
Must be
CH3 – CHBr2 (This is however, right answer)
(ii) CH 2 CH 2
Br Br
(iii) CH3 CH CH2

Br Br
Wrong
H
(iv) CH3 CH B H (If actually, it is boron then Boron must have negative charge)
Br Br
SECTION - B
Objective Type Questions
1. Which of the following is least reactive towards SN2 mechanism?
Cl Cl CH2 Cl
(1) (2) CH2==CH—CH2—Cl (3) (4)
Sol. Answer (3)
Cl
will be last reactive in SN2 reaction because the planar transition state involved in this case would be
extremly unstable because of ring strain in three membered ring is very high.
CH3
Cl2/h NaOH
2. excess A B
CH3
How many moles of CH3OH required to react completely with B ?
(1) One (2) Two (3) Three (4) Four

Sol. Answer (2)
CH3 CH2 – Cl CH2Cl
Cl2 / h Cl2 / h (A)
CH3 CH3 CH2
2NaOH
Cl
OH
HO
(B)
Cl
Na Br2/
3. dry ether
A 1 eq.
B
alc. KCN
Cl H3O
+
D 1 mol
C
Product D in the reaction is
(1) Optically active cyanide (2) Optically inactive acid
(3) Optically active acid (4) Optically active aldehyde
Sol. Answer (2)
Cl
Na Br2/
ether 1 eq.
(B)
Cl (A) Br
alc KCN
+
H3O
1 mol.
COOH CN
(D) (C)
Optically inactive
4. Which of the following is the least volatile?
(1) CH3—CH2—CH2—F (2) CH3—CH2—CH2—Cl
(3) CH3—CH—CH3 (4) CH3—CH2—CH2—Br
Br
Sol. Answer (4)
B.P. size of molecule
∵ of van der Waal's force of attraction.
Br
Among the following has highest boiling point.
1
Also, V.P 
B.P
Hence, smaller the V.P (Vapour pressure) lower will be volatility.
5. Which of the following will be readily soluble in water?
Cl Cl
(1) Cl (2) Cl (3) (4)
Sol. Answer (2)
+
Cl +
(Allyl halide)
This is good substrate for both SN1 and SN2 reaction.
6. Which one of the following is a free-radical substitution reaction?
CH3 Boiling CH2Cl

(1) + Cl2
Anh. AlCl3 CH3

(2) + CH3Cl
CH2Cl CH2NO2
(3) + AgNO2
(4) CH3CHO + HCN  CH3CH(OH)CN
Sol. Answer (1)
CH 3
+ Cl2
Boiling Cl
Mech - Cl – Cl  2Cl
CH2 – H + Cl CH2 + HCl
CH2 + Cl CH2Cl
7. Which of the following compounds undergoes nucleophilic substitution reaction most easily?
Cl
Cl
(1) (2)
OCH3
Cl
Cl
(3) (4)
NO2
CH3
Sol. Answer (3)

Cl Cl Nu Cl Nu
–
O Nu :
N
Slow (RDS)
O N
O N
O O
Carbanion O
(intermediate)
Cl Nu
N
O
O
Nu
N
O
O
8. Replacement of Cl of chlorobenzene to give phenol requires drastic conditions. But chlorine of

2, 4-dinitrochlorobenzene is readily replaced
(1) NO2 donates electron at meta position (2) NO2 withdraws electron from ortho/para positions
(3) NO2 make ring electron rich at ortho & para (4) NO2 withdraws electron from meta position
Sol. Answer (2)
This is again ArSN reaction. The intermediate of this reaction is carbanion, whose stability can be increase
by electron withdrawing group like –NO2.
9. Chloropicrin is obtained by the reaction of

(1) Steam on carbon tetrachloride (2) Nitric acid on chlorobenzene
(3) Chlorine on pricric acid (4) Nitric acid on chloroform
Sol. Answer (4)
Nitric acid Chloroform

HNO3   CHCl3 
 Chloropicrin
CCl3NO2
10. The reaction of toluene with Cl2 in presence of FeCl3 gives X and reaction in presence of light gives Y. Thus, X and
Y are
(1) X = Benzyl chloride, Y = m-chlorotoluene
(2) X = Benzal chloride, Y = o-chlorotoluene
(3) X = m-chlorotoluene, Y = p-chlorotoluene
(4) Y = o- and p-chlorotoluene, Y = Trichloromethyl benzene
Sol. Answer (4)
CH3 CH3 CH3
Cl
Cl2 Anhy
+ Cl2 AlCl3
+
h
CCl3 Cl (Ortho)
(Para)
Major
CH2OH
dry ether
+ HCl A + Mg B
11. (excess)
OH
What is B?
CH3
CH2MgCl CH2OH CH3
(1) (2) (3) (4)
– +
Cl O Mg Cl
MgCl MgCl
Sol. Answer (4)
OH Cl MgCl CH3
Mg acid-base
+ HCl
dry ether reaction
OH OH OH –
O Mg Cl
+
(A) (B)
12. Ethylidene chloride reacts with aq. KOH to form which of the following compound?
(1) Acetaldehyde (2) Ethylene glycol (3) Ethyl alcohol (4) Acetic acid
Sol. Answer (1)
Clearly, Acetaldehyde will form.
13. The correct order of reactivity of the following compounds towards aqueous NaCN will be
Cl
Cl
I. II. CH2 = CH—CH2—Cl III. CH3 — CH — CH 3 IV. CH2 = CH—CH2—Br
(1) I > II > III > IV (2) I > IV > II > III (3) IV > II > I > III (4) IV > II > III > I
Sol. Answer (4)
1. SN reaction order
at allylic carbon atom >> at vinylic 'C' atom.
∵ In case of vinylic 'c', bond strength is more due to resonance which decreases SN1 or SN2 reactivity.
Cl Cl
i.e., SN reactivity order C C << C C C
Vinylic ‘C’ allylic 'C'
2. SN reaction and leaving tendency of the group.
 SN reactivity order in terms of leaving group.
–I > –Br > –Cl > – F
3. Case of B – unsaturation increases the SN1 or SN2 reactivity order.
 Keeping three concept, we can find the case of reaction with NaCN (SN2 order)
Br Cl
> > Cl > Cl
14. Which among the following is the correct order of melting point?
Cl Cl Cl Cl Cl Cl
Cl Cl
(1) > > (2) > >
Cl Cl
Cl Cl
Cl Cl Cl Cl Cl Cl
Cl Cl
(3) > > (4) > >
Cl Cl
Cl Cl
Sol. Answer (3)
Cl Cl Cl
Cl
The correct order of melting point is > >
Cl
Cl
This is because of more symmetrical structure and tight crystal packing.
Cl OH
15. + aq. KOH
G G
For which of the following G, above reaction will be the fastest?
(1) –OH (2) –CH3 (3) –NO2 (4) –CHO
Sol. Answer (3)
As the reaction proceed the SNAr mechanism.

So, intermediate is carbanion,
 G must be electron withdrawing group (–R) effect, in order to stabilize the intermediate carbanion.
16. Which of the following is least reactive towards nucleophilic substitution?
F Cl Br I
NO2 NO2 NO2 NO2
(1) (2) (3) (4)
Sol. Answer (4)
F Cl Br I
NO2 NO2 NO2 NO2
> > >
∵ In SNAr the attack of nucleophile is the r.d.s. So, more is the charge on target 'C' atom, more is the SNAr
reactivity.
Reactivity order towards ArSN
17. Among the following

Cl Cl Cl Cl
NO2 NO2
NO2
NO2 NO2
I II III IV
The correct order of reactivity towards ArSN mechanism is
(1) I > III > II > IV (2) I > II > IV > III (3) III > II > IV > I (4) I > IV > II > III
Sol. Answer (4)
Cl Cl Cl Cl
NO2 NO2
> > >
NO2
NO2 NO2
∵ In SNAr intermediate is carbanion so, electron withdrawing group increases the reactivity.
18. Which of the following does not give yellow precipitate with AgNO3?
(1) (CH3)3C—CH2 —I (2) CH2 ==CH—CH2—I
(3) CH2 C CH3 (4) CH CH3
Sol. Answer (3)
CH2 C CH3 + AgNO3  No reaction
(Vinyl Halide)
∵ Vinylic cation is highly unstable, i.e.
Stability
C C C C C
order
C–OH
19. + CH3MgCl A + Cl2
(1 mole)
h
dry ether
C Na + B
What is C?
O
C
(1) CH3–CH3 (2)
CH3
OH
C CH3
(3) (4) CH2 = CH2
CH3
Sol. Answer (1)
O O
C – OH C–OMgCl
+ CH3MgCl + CH4
(A)
Cl2, (1 mol)
h
CH3 – Cl
Na
CH3 – CH3 (B)
dry ether
(Wurtz (C)
product)
CH3 H 1% cold
Br2 Zn/ether KMnO4/OH
20. C C CCl4
A B C
H CH3
The product (C) is
CH3 CH3 CH3

H OH HO H H OH
(1) (2) (3) (4) Mixture of (1) & (2)
HO H H OH H OH
CH3 CH3 CH3
Sol. Answer (4)
CH3 Br
CH3 H
Br2 H Br CH3 H
+ CCl4 H Br CH3 H
H CH3
CH3 Br
(trans)
Anti addition
CH3
H
CH3 H
Br
Br
CH3
Br H
CH3 H
Zn/ether
Br
H Cis CH3 H CH3
–
Syn KMNO4/OH
addition CH3 CH3
1%
H
Racemic Mix i.e. H OH
+ HO
HO H H OH
CH3 CH3
d - l mix
Note :
Trans alkene  meso comp.

anti addition
Trans alkene  d-l mix

syn addition
Cis alkene     d-l mix

anti addition
Cis alkene  meso comp.

anti addition
21. In the given reaction

Br
S
CH3 H Zn/ether
R Product (Major)
H Br
CH3
The product will be
(1) Cis-2-butene (2) Trans-2-butene (3) 2-butyne (4) Buta-1, 3-diene
Sol. Answer (2)

Br
CH3 H
CH3 H Zn/ether
H Br
H CH3
CH3 (Trans-2-Butene)
22. Under identical conditions, solvolysis of which of the following substrate would lead to maximum racemisation?
CH3
H Br
CH3 CH3 Br
(1) H D (2) (3) Br NO2 (4) C6H5 D
Br H CH3
OCH3
Sol. Answer (2)
CH3
H Br
SN1
+ H2O Racemisation
OCH3
This is fast reaction because the intermediate carbocation thus formed is 2° benzylie and stabilised by (+M) effect
of –OCH3 group placed at para position.
CH3
H C
∵ Intermediate is
OCH3
23. The correct orders of reactivity towards SN1 reaction is
Cl
Cl CH2 Cl
CH3
I II III
(1) I > II > III (2) II > III > I (3) III > II > I (4) I > III > II
Sol. Answer (2)
For SN1 reaction the correct order of reactivity would be
Cl
Bridge 'C'
Cl Cl
CH3 > >
(3°) (2°) (Bridgehead)
Note : Bridgehead carbocation is highly unstable, because sp2 hybridisation is not possible al bridge 'C' atom.
24. When cis-but-2-ene is treated with Br2 in CCl4 medium the product formed will be
(1) (2R, 3S) dibromobutane (2) (2R, 3R) dibromobutane
(3) (2S, 3S) dibromobutane (4) Mixture of (2R, 3R) and (2S, 3S) dibromobutane
Sol. Answer (4)
CH3 CH3
CCl4
+ Br2 Racemic mixture
H (Cis) H
In Br2 / CCl4, anti addition reaction follows and as we know,
Cis  Cl & l mix

anti addition
 Racemic mix is formed.
Acetone
25. CH3—Cl + NaI CH3—I + NaCl
Above equilibrium is more towards right because

(1) NaI is more reactive than NaCl (2) CH3I is more reactive than CH3Cl
(3) NaCl is less soluble than NaI in acetone (4) It is Finkelstein’s reaction
Sol. Answer (3)
Acetone
CH3  Cl  NaI
CH3  I  NaCl
 Soluble Precipitates out 
SECTION - C
Previous Years Questions
1. Identify A and predict the type of reaction
OCH3
NaNH2
A [NEET-2017]
Br
OCH3
(1) and substitution reaction

NH2
OCH3
NH2
(2) and elimination addition reaction
OCH3
Br
(3) and cine substitution reaction
OCH3
(4) and cine substitution reaction
Sol. Answer (1)

OCH3 OCH3 OCH3
H
NH2
Br Br
Benzyne
OCH3
NH2
OCH3 X
a
(Less stable)
NH2
OCH3
OCH3
b H–NH2
NH2
NH2
More stable as –ve charge is close to electron withdrawing group
∵ Incoming nucleophile ends on same ‘C’ on which ‘Br’ (Leaving group) was present
 NOT cine substitution.
2. Consider the reaction [NEET-(Phase-2)-2016]
CH3CH2CH2Br + NaCN  CH3CH2CH2CN + NaBr
This reaction will be the fastest in
(1) Ethanol (2) Methanol
(3) N, N-dimethylformamide (DMF) (4) Water
Sol. Answer (3)
∵ The reaction is SN2, most suitable solvent should be polar aprotic i.e., DMF.
3. Which of the following biphenyl is optically active? [NEET-2016]
CH3 O2N
(1) (2)
CH3 I
Br Br I
(3) (4)
I I I
Sol. Answer (3)
Due to steric hindrance, arising due to presence of bulkier groups at ortho-positions of benzene rings, the
biphenyl system becomes non-planar i.e., optically active.
4. Two possible stereo-structures of CH3CHOH.COOH, which are optically active, are called [Re-AIPMT-2015]
(1) Enantiomers (2) Mesomers
(3) Diastereomers (4) Atropisomers
Sol. Answer (1)
CH3 CH3
C C
COOH OH
HO CH3 HOOC CH3
ENANTIOMERS
5. In an SN1 reaction on chiral centres, there is [Re-AIPMT-2015]

(1) 100% retention
(2) 100% inversion
(3) 100% racemization
(4) Inversion more than retention leading to partial racemization
Sol. Answer (4)
Fact.
6. In which of the following compounds, the C – Cl bond ionisation shall give most stable carbonium ion?
[AIPMT-2015]
H
H3C CH — Cl
H H3C H C — Cl
(1) C — Cl (2) C — Cl (3) H C
3
(4)
O2NH2C H H3C CH3
Sol. Answer (3)

The relative stability order of the carbonium ions is as follows.
CH2
CH3
H3C C H3C CH CH3 O2N CH2 CH2
CH3
this stablity is on the basis of extent of resonance, hyperconjugation and inductions effect. Which also
Satisfy the experimental facts. So, the correct answer is (3).
7. What products are formed when the following compound is treated with Br2 in the presence of FeBr3?
CH 3
[AIPMT-2014]
CH3
CH 3
CH 3 CH3 CH 3
Br Br Br
(1) and CH3 (2) and
CH3 Br CH3 CH3
CH 3 CH 3
CH3 CH3
Br
(3) and (4) CH3 and
CH3 CH3 Br CH3
Br Br
Sol. Answer (3)
–CH3 group is o, p - directing.
8. Which of the following compounds will undergo racemisation when solution of KOH hydrolyses ?
CH3
CH2Cl CH3
(i) (ii) CH3CH2CH2Cl (iii) H3C–CH–CH2Cl (iv) H C Cl
C2H5
[AIPMT-2014]
(1) (i) and (ii) (2) (ii) and (iv) (3) (iii) and (iv) (4) (i) and (iv)
Sol. Answer (4)
9. In the replacement reaction Cl + MF CF + M . The reaction will be most favourable if M happens to be
[AIPMT (Mains)-2012]
(1) Na (2) K (3) Rb (4) Li
Sol. Answer (3)
The reaction is SN1. The reaction will be more favoured when there is more release of F– which depends upon
polarising power of metal. Size of Rb is largest among the given options so more release of F– will take place.
10. Which of the following compounds undergoes nucleophilic substitution reaction most easily ?
[AIPMT (Mains)-2011]
Cl Cl
Cl Cl
(1) (2) (3) (4)
NO2
OCH3 CH3
Sol. Answer (3)
Cl
has electron withdrawing group NO2 which reduces the double bond character between carbon of benzene
NO2
ring and chlorine.
11. Consider the reactions
C2H5 OH
(i) (CH3)2CH – CH2Br   (CH3)2CH–CH2OC2H5 + HBr
C H O
(ii) (CH3)2CH – CH2Br 
2 5
 (CH3)2CH–CH2OC2H5 + Br–
The mechanisms of reactions (i) and (ii) are respectively [AIPMT (Mains)-2011]
(1) SN2 and SN2 (2) SN2 and SN1 (3) SN1 and SN2 (4) SN1 and SN1
Sol. Answer (1)
CH3 CH3
C2H5OH
CH CH2 Br CH CH2 – O – C2H5
SN1
CH3 CH3
–
SN2 C2H5O
CH3
CH CH2 OC2H5
CH3
Nucleophilicity order C2H5O– > C2H5OH more is the Nu order more is SN2 on 1°R – L oir 2°B – L.
12. The correct order of increasing reactivity of C–X bond towards nucleophile in the following compound is
X
X NO2
I. II. III. (CH3)3C – X IV. (CH3)2CH – X
NO2
[AIPMT (Prelims)-2010]
(1) I < II < IV < III (2) II < III < I < IV (3) IV < III < I < II (4) III < II < I < IV
Sol. Answer (1)
X X
CH3 H NO2
CH3 C X > CH3 C X > >
CH3 CH3 (Worst with all)
NO2
with SN1 ArSN
13. Which one is most reactive towards SN1 reaction ? [AIPMT (Prelims)-2010]
(1) C6H5CH(C6H5)Br (2) C6H5CH(CH3)Br (3) C6H5C(CH3) (C6H5)Br (4) C6H5CH2Br
Sol. Answer (3)
CH3 CH3
RDS
C Br C
(Slow)
(3°, benzylie most stable)
Hence, SN1 reaction will occur most easily here.
1. Mg,Ether
14. In the following reaction, C6H5CH2Br 
2. H O
 X, the product 'X' is [AIPMT (Mains)-2010]
3
(1) C6H5CH2OCH2C6H5 (2) C6H5CH2OH (3) C6H5CH3 (4) C6H5CH2CH2C6H5

Sol. Answer (3)
(1) Mg, ether
CH2Br +
(2) H3O
Mechanism – CH2MgBr
(Acid-Base H O+
3
reaction)
Br
CH3 + Mg
OH
(Toluene)
Magnesium
hydroxy
Bromide
15. Which of the following reactions is an example of nucleophilic substitution reaction? [AIPMT (Prelims)-2009]
(1) 2 RX + 2 Na  R–R + 2 NaX (2) RX + H2  RH + HX
(3) RX + Mg  RMgX (4) RX + KOH ROH + KX
Sol. Answer (4)
   
R  X  K OH  R  OH  KX
This is an example of nucleophilic substitution reaction.
16. H3C–CH–CH=CH2 + HBr  A

CH3
A (predominantly) is [AIPMT (Prelims)-2008]
(1) CH3–CH–CH–CH3 (2) CH3–CH–CH2–CH2Br

CH3 Br CH3
Br
(3) CH3–C–CH2CH3 (4) CH3–CH–CH–CH3
CH3 Br CH3
Sol. Answer (3)
17. In a SN2 substitution reaction of the type

DMF 
R–Br+Cl–  R – Cl + Br–
Which one of the following has the highest relative rate? [AIPMT (Prelims)-2008]
CH3
(1) CH3CH2Br (2) CH3–CH2–CH2Br (3) CH3 – CH – CH2Br (4) CH3 – C – CH2Br
CH3 CH3
Sol. Answer (1)
As in aprotic polar solvent, SN2 is favoured & DMF is aprotic polar solvent.
DMF
CH3  CH2  Br  Cl   CH3  CH2  Cl  Br 
S 2 N
This will occur fastest because of less steric hindrance in transition state.
18. If there is no rotation of plane polarized light by a compound in a specific solvent, thought to be chiral, it may
mean that [AIPMT (Prelims)-2007]
(1) The compound may be a racemic mixture (2) The compound is certainly a chiral
(3) The compound is certainly meso (4) There is no compound in the solvent
Sol. Answer (3)
19. For the following

a. I–
b. Cl–
c. Br–
The increasing order of nucleophilicity would be [AIPMT (Prelims)-2007]
(1) Br– < Cl– < I– (2) I– < Br– < Cl– (3) Cl– < Br– < l– (4) I– < Cl– < Br–
Sol. Answer (3)
The increasing order of nucleophilicity would be
Cl– < Br – < I–
20. Which of the following undergoes nucleophilic substitution exclusively by SN1 mechanism ?
[AIPMT (Prelims)-2005]
(1) Benzyl chloride (2) Ethyl chloride (3) Chlorobenzene (4) Isopropyl chloride
Sol. Answer (1)
Br
C
21. The chirality of the compound H3C H is [AIPMT (Prelims)-2005]
Cl
(1) R (2) S (3) Z (4) E
Sol. Answer (1)
+
H3O CaO
22. C5H11Br + NaCN A B + NaOH C
‘C’ has the formula C5H12 which can give four isomeric monochloro derivative. What is the structure of C5H11Br?
Br
(1) CH3 — CH — CH2 — CH2 — Br (2) CH CH 2 CH CH 2 CH3
3
CH3
CH3
(3) CH3 — CH2 — CH2— CH — CH3 (4) CH2 — C — CH2 —Br
Br CH3
Sol. Answer (1)

Given, C is C5H12
The degree of unsaturation of C is
H  X  N
D° = C + 1 –
2
12
= 5  1 =6–6=0
2
Moreover, it forms four isomeric monochloro derivative.
∵ it must have
Hence, as per reaction sequence the structure of the compound is

Br
23. CD2 = CH – CH2 – Br is subjected to SN1 and SN2 reactions separately, which of the following statement is
correct?
(1) Both SN1 and SN2 give two products
(2) Both SN1 and SN2 give only one product
(3) SN1 gives two products but SN2 gives only one product
(4) SN1 gives one product but SN2 gives two products
Sol. Answer (3)
Br SN 1 Nu
D2C D2C
+
SN2
Nu
Nu
D2C D D
24. In Finkelstein reaction when acetone is replaced by water then

(1) Reaction occurs in forward direction via SN1 pathway
(2) Reaction occurs in forward direction via SN2 pathway
(3) Reaction occurs in backward because NaCl formed in right hand side is soluble in water and cannot ppt.
out
(4) Reaction is not possible
Sol. Answer (3)
In Finkelstein reaction
Acetone
CH3  Cl  NaI  CH3I  NaCl ppt
This reaction is in forward direction, only
H O
However, CH3Cl  NaI
2
CH3I  NaCl

Soluble
SN2 reaction is favourable in aprotic polar solvent like acetone, DMSO, DMF. So, the reaction is SN2 pathway
in forward direction. Again, since. NaCl ppt out in acetone solvent.
 backward reaction is not possible, i.e.,
H3C  Cl  NaI  CH3I  NaCl 
 S
25. Which graph is incorrect?
Rate
(1) Rate (2)
Base Base
For Ph3CBr + OH–  Product For (CH3)2CHBr + OH– (in acetone) Product
(3) Ea (4)
P.E.
Reaction
Reaction
Progress
Progress
For PhCHDBr + BrOH  Product For Me2(Et) COTs + NH3  Product
Sol. Answer (3)
The choice (3) given to us is incorrect simply because this is SN1 reaction
and the C+ thus formed is stable will not ungergo furthur rearrangement.
So, number of intermediates = 1 E
Number of transition states = 2
26. Which will undergo fastest SN2 substitution reaction when treated with NaOH? Reaction Progress 
CH3 CH3
(1) H5C2 C Br (2) CH3 C Br
H CH3
CH3 H
(3) D C Br (4) H C CH2 — CH2 — CH3
C2H5 Br
Sol. Answer (4)

Obviously, for SN2, 1° substrate is always the first choice
Hence, last option or Br
SN2 reactivity order

H3C – L > 1° R – L > 2° R – L > 3° R – L
Where L = L.G.
27. Given reaction
ether (i) H O
2
Br Mg X (ii) HCl Y(main product)
Y in the reaction is
(1) Hexane (2) Cyclohexane
(3) Cyclohexylcyclohexane (4) Cyclohexyl ether
Sol. Answer (2)
Mg H2O/HCl
Br MgBr
ether Acid-Base
Cyclohexane
+
Mg
HO Br
28. Which one of the following alkyl bromides undergoes most rapid solvolysis in methanol solution to give corresponding
methyl ether?
CH2
(1) =C Br (2) Br
H
(3) (4)
Br
Br
Sol. Answer (1)
Because allylic cation is more stable due to resonance.
C C CH2 C CH CH2
CH3 Br CH3 OMe

MeOH
(Allylic)
+
CH3 CH3 (Major)
MeO
Me Me
29. Monobromination of 2-methylbutane gives how many distinct structural isomers?

(1) One (2) Two (3) Three (4) Four
Sol. Answer (4)
Br
Br2, h + + +
Br
Br
Br
Four monobromo derivatives

30. When CH3CH2CHCl2 is treated with NaNH2, the product formed is
(1) CH3 – CH = CH2 (2) CH3 – C  CH
NH2 Cl
(3) CH 3CH 2CH (4) CH3CH2CH
NH2 NH2
Sol. Answer (2)
Cl
2NH2
CH3 C CH
Cl
(Propyne)
31. Grignard reagent is prepared by the reaction between
(1) Magnesium and alkane
(2) Magnesium and aromatic hydrocarbon
(3) Zinc and alkyl halide
(4) Magnesium and alkyl halide
Sol. Answer (4)
R  X  Mg  
 R  MgX
Oxidative
insertion
The solvent used is dry ether.
32. The following reaction is described as
H3C – (CH2)5 (CH2)5CH3

H H
–
OH
C Br HO C
H3C CH3
(1) SN2 (2) SN0 (3) SE2 (4) SN1

Sol. Answer (1)
CH3 – (CH2)5 (CH2)5 CH3

–
OH
CH – Br HO – CH
SN2
CH3 CH3
As 1°R – X follows SM2 and 2°R – X path.
33. 2-Bromopentane is heated with potassium ethoxide in ethanol. The major product obtained is
(1) trans-pentene-2 (2) Pentene-1
(3) 2-ethoxypentane (4) cis-pentene-2
Sol. Answer (1)
Br
– +
(Major)
Eto N a +
ethanol (Terminal) (Trans)
+
(cis)
34. Which of the following compounds is not chiral?

(1) CH3CHDCH2Cl (2) CH3CH2CHDCl
(3) DCH2CH2CH2Cl (4) CH3CHClCH2D
Sol. Answer (3)
DCH2 – CH2 – CH2 – Cl
Achiral molecule
35. An organic compound A(C4H9Cl) on reaction with Na/diethyl ether gives a hydrocarbon which on monochlorination
gives only one chloro derivative then, A is
(1) t-butyl chloride (2) Secondary butyl chloride
(3) Isobutyl chloride (4) n-butyl chloride
Sol. Answer (1)
A (C4H9Cl) must be Cl
Moreover, Dry
Cl + Na + Cl ether
(t-butyl chloride)
This will give only one product

on monochlorination
36. Reactivity order of halides for dehydrohalogenation is
(1) R – F > R – Cl > R – Br > R – I (2) R – I > R – Br > R – Cl > R – F
(3) R – I > R – Cl > R – Br > R – F (4) R – F > R – l > R – Br > R – Cl
Sol. Answer (2)
For dehydrohalogenation reaction, the alkyl halide must have better having group.
i.e., R – I > R – Br > R – Cl > R – F

As the order of L.G. among halide is : I– > Br– > Cl– > F–
NaCN Ni / H2
37. CH3CH2Cl X Y
Y in the above reacting sequence is
(1) CH3CH2CH2NHCOCH3 (2) CH3CH2CH2NH2
(3) CH3CH2CH2CONHCH3 (4) CH3CH2CH2CONHCOCH3
Sol. Answer (2)
CH3 – CH2 – Cl CH3 – CH2 – CN
(X)
Ni/H2
CH3 – CH2 – CH2NH2
(Y)
38. Which of the following is least reactive in a nucleophilic substitution reaction?

(1) (CH3)3C – Cl (2) CH2 = CHCl
(3) CH3CH2Cl (4) CH2 = CHCH2Cl
Sol. Answer (2)
In nucleophilic substitution reaction wheather (SN1 or SN2), Vinyl halide is always least reactive.
Cl
Vinyl halide
39. Which of the following is not chiral?
(1) 2-hydroxypropanoic acid
(2) 2-butanol
(3) 2,3-dibromopentane
(4) 3-bromopentane
Sol. Answer (4)
OH
OH
(1) *
(Chiral)
O
OH
(2)
* (Chiral)
Br
*
(3) *
(Chiral)
Br
(4)
Br
SECTION - D
Assertion-Reason Type Questions
1. A : When chloroform is obtained from bleaching powder and ethanol then chlorine acts as oxidising agent only.
R : It oxidises ethanol into acetic acid.
Sol. Answer (4)
O O
Cl2 + OH
C
(From bleaching
–
powder) Cl2, OH H3C H
–
CHCl3 + HCOO
Hence, both Assertion and reason are false.
2. A : Dow's process is an example of nucleophilic substitution reaction.

R : In this process, benzyne is formed as an intermediate.
Sol. Answer (2)
Cl OH
H OH
–
–
OH
(Benzyne) Phenol
Both assertion and reason are true, however the reason is not a correct explanation.
3. A : In presence of DMSO solvent, the rate of SN2 reaction increases.

R : DMSO is a polar protic solvent.
Sol. Answer (3)
DMSO is a aprotic polar solvent
O
S
H3C CH3 Dimethyl sulphoxide
Polar aprotic solvents like DMSO accelerate the SN2 rate.
∵ , Assertion is true, Reason is false.
4. A : When alkyl halide is reacted with AgCN then alkyl isocyanide is formed.
R : AgCN is a covalent compound and only the site of nitrogen is available for the reaction.
Sol. Answer (1)

R  X  AgCN  R N C
Covalent 
∵ Assertion is true.
Reason is true with correct explanation.
5. A : In Hunsdiecker reaction, alkyl chloride is formed in poor yield.

R : In this reaction, carbanion is formed as an intermediate.
Sol. Answer (3)
Hunsdiecker reaction gives poor yield of alkyl halide the reaction invloves free radical mechanism.
∵ Assertion is true, Reason is false.
6. A : Ethylidene chloride on alkaline hydrolysis gives acetaldehyde.

R : Two chlorine atoms attached with adjacent carbon atom in alkylidene chloride.
Sol. Answer (3)
No doubt, simply
∵ Assertion is true, Reason is false.
7. A : Primary alkyl halides on oxidation with DMSO gives aldehydes.

R : DMSO is used as polar aprotic solvent.
Sol. Answer (2)
DMSO is polar aprotic solvent
O
S
H3C CH3 Dimethyl sulphoxide
Primary alkyl halide 

DMSO
 R  CHO
Heat  Aldehyde 
∵ Assertion is true, Reason is correct but not the explanation of Assertion.
8. A : Haloalkanes react with KCN to give alkyl cyanide as the main product while with AgCN they form
isocyanide as the main product.
R : In KCN, K form ionic bond due to which one lone pair present on carbon, so carbon act as donor but in
AgCN, Ag form covalent bond and carbon has no lone pair so N-atom act as donor.
Sol. Answer (1)
AgCN KCN
R  N C   R  X  R  CN
Because AgCN  Covalent

KCN  Ionic
Both the assertion and reasons are correct.
9. A : In benzyne the hybridisation of triply bonded carbon is sp2.

R : The second -bond is formed by sp2 hybrid orbital.
Sol. Answer (1)
2
sp
(Abnormal  bond)
2
sp
∵ Both assertion and reason are correct.
10. A : Halogen is deactivating group due to –I effect.

R : Halogen is ortho-para directing due to +M effect.
Sol. Answer (2)
Halogens show (–I) effect as well as (+M)/(+R) effect.
These are O/P directing because of (+M) effect.
Cl Cl
NO2
11. A : is more reactive towards nucleophilic substitution reaction than .
NO2
R : NO2 group is electron withdrawaing so decreases the double bond character of C–Cl bond.
Sol. Answer (3)
Cl Cl
NO2
>
NO2
(ArSN)
The reaction occurs via ArSN mechanism and the formation of carbanion is rate determining step (Slow step).
Cl
12. A : on reaction with alcoholic KOH gives .
D
H
R : Bond energy of C–D bond is less than that of C–H bond.
Sol. Answer (3)
Cl
KOH
+
D D
H
This is E2 reaction, it demands Anti-periplanar transition state.
13. A : Meso-2, 3-dibromobutane on reaction with Zn/ether gives trans but-2-ene.

R : Zn/ether gives anti-elimination.
Sol. Answer (1)
CH3
H Br
Zn/ether
(Anti ellimination) (Major)
H Br
CH3
14. A : The number of optically active isomers of tartaric acid is two.

R : Tartaric acid contains two asymmetric carbon.
Sol. Answer (2)
COOH COOH
H * OH HO H
HO * H H OH
COOH COOH
Both are optically active
15. A : Chlorobenzene on reaction with sodium metal in the presence of dry ether gives diphenyl.
R : This reaction is called Ullmann reaction.
Sol. Answer (3)
Cl + Na + Cl
Dry ether
Biphenyl
This reaction is called Fitting reaction.


10 Haloalkanes and Haloarenes: Solutions

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10 Haloalkanes and Haloarenes: Solutions

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Chapter 10

Haloalkanes and Haloarenes

Objective Type Questions

1. Which of the following is a secondary alkyl halide?

We have Isobutyl chloride

2. The IUPAC name of the compound

(1) 4-Bromobut-2-ene (2) 1-Bromobut-2-ene (3) 3-Bromobut-2-ene (4) Allyl bromide

Sol. Answer (2)

 (2) is the correct option

3. Which of the following may be classified as an aryl halide?

(1) CH2 Cl (2) CH3 CH2 Cl

(3) CH3 Cl (4)

Sol. Answer (3)

4. Which of the following belongs to the class of vinyl halides?

6. The addition of HBr is easiest with

CH3 CH3 – CH3

7. CH2 CH NO2 + HBr P ; The major product ‘P’ is

8. The intermediate during the addition of HCl to propene in presence of peroxide is

11. CH3 CH CH2 + HOBr P ; The major product ‘P’ is

Sol. Answer (2)

Sol. Answer (2)

Hence, the above product formed reflects Anti-markovnikov's reaction.

CH3 CH3 CH2 Cl CH3

Sol. Answer (3)

(Free radical Halogenation)

CH2Br CH3 CH3 CH3

Sol. Answer (3)

CH3 CH3 CH3

16. Which is most stable radical?

(1) CH3 (2) CH 2 CH CH 2 (3) CH 3 CH 2 (4)

Sol. Answer (2)

Because of resonance allylic radicals are stable.

the electrophilic aromatic substitution reaction.

(1) Nucleophilic substitution (2) Free radical addition

This is electrophilic aromatic substitution.

(1) Sandmeyer (2) Swarts (3) Wurtz-Fittig (4) Finkelstein

This is sandmeyer reaction.

22. Which is most reactive nucleophile in polar protic solvent?

23. Which is most reactive nucleophile in polar aprotic solvent?

24. Which cannot act as an ambident nucleophile?

(1) CN– (2) NO2− (3) SCN– (4) OH–

Sol. Answer (4)

This is SN2 reaction.

CH3 CH3 CH3 CH2 H

Sol. Answer (1)

30. An SN2 reaction at an asymmetric carbon of a compound always gives

COOH CH3 CH2 COOH CH3

(1) (2) (3) (4)

Sol. Answer (3)

(A) (B) (C)

Hence, the product (C) is an acid shown.

32. Which one is the most reactive towards SN1 reaction?

The reaction goes through

(1) SN1 (2) SN2 (3) E2 (4) E1

Sol. Answer (2)

34. The order of E2 elimination for alkyl halide is

NO2 NO2 NO2

Sol. Answer (4)

The reaction occurs via benzyne mechanism.

(1) N2 (2) CHCl3/KOH (alcoholic) (3) NH3 (4) KCN

Sol. Answer (2)

R must be CHCl3, OH–