OM Coaching classes

NEET / JEE (Medical and Engg.)

11

Section - B (Chemistry) Marks: 180 Date: 30 / 04 / 2023

Roll No. Test No.

This is to certify that the name has been correctly written and verified.
Topic : HALOGEN DERIVATIVES AND ALKENES

Candidate’s Signature
NEET
Name : ________________________ Invigilator’s Signature

Note: (1) All questions are compulsory.

(2) Select the most correct answer and darken (  ) the circle (  ) corresponding to correct alternative.
01) The synthesis of alkyl fluorides is best Cl 2
CH3 - CH2 - CH3 
 CH - CH - CH - Cl
h 3 2 2
accomplished by
1) Finkelstein reaction + CH3  CH  CH3
2) Swarts reaction |
3) Free redical fluorination Cl
4) Sandmeyer’s reaction.
Key: 2) by the action of AsF3, SbF3, CoF3, AgF, HgF, 04) The following reaction
Hg2F2, etc. on reaction with R - Br R - Cl + NaI   R - I + NaCl
Acetone

CH3Br + AgF  CH3F + AgBr is known as

This reaction is called Swarts reaction. 1) Frankland reaction
2) Swarts reaction
02) Which of the following is not an allylic halide? 3) Etard reaction
1) 4 - bromopent - 2 - ene 4) Finkelstein reaction
2) 3 - Bromo - 2- methylbut - 1 - ene Key: 4) It is Finkelstein reaction in which alkyl
3) 1 - Bromobut - 2 - ene chlorides or bromides react with NaI in presence
4) 4 - Bromobut - 1 - ene of acetone to give alkyl iodide.
Key: 4) Except 4-Bromobut-l-ene all are allylic R - Cl + NaI   R - I + NaCl
Acetone
halides.
Br - CH2 - CH2 - CH = CH2
05) Alkyl halides are less soluble in water because
1) they ionise in water
03) The number of isomeric halopropanes
2) they do not form H-bonds with water
produced, when propane gets halogenated is
3) they are highly viscous
1) 1 2) 2
4) they have very strong C - X bond.
3) 4 4) 3
Key: 2) They are polar but fail to form H - bonds
Key: 2) Propane has two types of C - atoms. These
with water
are primary (10) and secondary (20) atoms,
hence, its
06) 3 - Methylpent - 2 - ene on reaction with HBr in 10) The major product of the following reaction is
presence of peroxide forms an addition product. CH 3
The number of possible stereoisomers for the |
C 2H 5ONa
product is C6H 5CH 2  C  CH 2  CH 3   
C 2H 5OH
1) two 2) four |
Br
3) six 4) zero
CH 3 1) C 6H 5CH 2  C  CH 2
| |
HBr
Key: 2) CH 3  CH 2  C  CH  CH 3 H CH 2CH 3
2O 2
3 - Methylpent - 2 - ene
2) C 6H 5CH  C  CH 2
|
CH 3 CH 2CH 3
|
*
CH 3  CH 2  C *  C H  CH 3 3) C 6H 5CH 2  C  CHCH 3
| | |
H Br CH 3

There are two chiral carbon atoms present in CH 3

the product. Therefore, total number of |
stereoisomers are = 2n = 22 = 4 4) C6H 5CH 2  C  CH 2CH3
|
07) Number of monochloro derivatives obtained OC 2H 5
when neo - pentane is chlorinated
1) one 2) two H CH 3
3) three 4) four. | | C 2H 5ONa
  
Key: 2) C 6H 5  CH  C  CH 2  CH 3  NaBr
CH3 CH 3 |  C 2 H 5 OH
| | Br
CH3  C  CH3 monochlorination CH 3  C  CH 2Cl
Key: 1) |     |
CH3 CH 3 CH 3
|
Neo - pentane C 6 H 5  CH  C  CH 2  CH 3
(all the position available
for chlorination are identical) 11) The increasing order of the reactivity of the
following halides for the SN1 reaction is
08) Which of the following compounds will not
react with ethanolic KCN? I) CH3  CH  CH 2  CH 3
|
1) Ethyl chloride Cl
2) Ethyl bromide
II) CH3CH2CH2Cl
3) Chlorobenzene
III) p - H3CO - C6H4 - CH2Cl
4) Allyl chlorde
1) (I) < (III)< (II) 2) (II) <(III)< (I)
Key: 3) Ethyl chloride, allyl chloride and ethyl
3) (III) <(II)< (I) 4) (II)<(I)< (III)
bromide react with alcoholic KCN by
Key: 4) More stable the carbocation formed, more
nucleophilic substitution reaction
rapidly that compound undergoes SN1 reaction.
Thus, only chlorobenzene will not react with 
KCN. CH3  CH  CH 2  CH 3 
Cl

|
Cl
09) Which of the following is the correct method of

preparation of methyl fluoride? CH3 - C H - CH2 - CH3
1) CH4 + HF  20 - carbocation.
2) CH3OH + HF 
3) CH4 + F2  CH3 - CH2 - CH2 - Cl 
Cl 

*4) CH3Br + AgF  
CH3 - CH2 - C H 2
2
 CH3
10 - carbocation CH3
CH2 - Cl
Cl 1) 2) H3C

H3CO CH 3
+
CH2 CH3
CH3
H3CO CH3
3) 4)
benzyl carbocation
(Resonance stabilse4) CH3

6
12) For the following compounds, the incorrect CH3
CH3 5
statement (s) with respect to nucleophilic O1
4 CHO
substitution reactions is (are) O3
Key: 4)  3 2
Zn / H 2O
CH3
CH3
5 - Keto - 2 - methylhexanal

(I) (II) 14) The correct order of increasing reactivity of the

CH3 following alkyl halides,
| Br
CH3  C  Br |
| I) CH 3  CH 2  CH  CH 3
CH3
II) CH3CH2CH2CH2Br
(III) (IV)
1) I and II follow SN2 mechanism CH 3
2) compound IV undergoes inversion of |
III) CH 3  C  CH 2  CH3
configuration |
3) the order of reactivity for I, III, and IV is : III > Cl
IV > I.
IV) CH3CH2CH2Cl
4) I and III follow SN1 mechanism.
towards SN2 displacement is
kEY 3) 1) Compounds I and II are 10 alkyl halides,
1) I < II < III < IV 2) III < I < IV < II
then they undergo SN2 mechanism.
3) III < I < II < IV 4) II < IV < I < III
2) Compound IV undergoes inversion of
kYE 2) Reactivity order of alkyl halides towards SN2
configuration due to intimate - ion pair
reaction follows the order.
formation inversion predominates over
Methyl halide > 10 > 20 > 30
retention.
Also, better the leaving groups, higher is the
3) Stability of carbocations follows the order:
reactivity. Br- is a better leaving group than Cl-.
20 benzylic > 30 alkyl > 10 benzylic
Thus, reactivity order towards SN2 reaction is
(IV) (III) (I)
4) I is a benzylic halide, thus, it undergoes SN1 (CH 3 )2 C  CH 2CH 3  CH 3CH 2CH  CH 3
reaction esily as benzylic carbocation is | |
resonance stabilised. III also follows S N1 Cl Br
(III) (I)
mechanism as it a 30 alkyl halide.
< CH3CH2CH2Cl < CH3CH2CH2CH2Br
13) Which compound would give 5 - keto - 2 - (IV) (II)
methyl- hexanal upon ozonolysis?
15) The conversion of ethyl bromide to ethyl iodide
using sodium iodide and dry acetone, this
reaction is known as
1) Swarts reaction 2) Finkelstein reaction
3) Sandmeyer reaction4) Stephen reaction.
3
Key: 2) Finkelstein reaction is used for the CH 3
preparation of alkyl iodides from alkyl chlorides |
10 0
or bromides using sodium or potassium iodide CH3CH2 - C H 2 - Br CH 3  CH 2  C 2  Br
and acetone. |
CH3CH2Br + KI  H
 CH3CH2I + KBr
Acetone

Ethyl bromide Ethyl iodide (n - Propyl bromide) (sec - Butyl bromide)

Thus, the order of reactivity is :
16) In the following reaction, the major product is (I) < (III) < (IV) < (II)
CH3
CH2 
1 equivalent HBr
19) The compound which on ozonolysis produces
   a mixture of propanone and ethanal is
H2C
1) 2 - methylbut - 1 - ene
CH3 CH3
CH3 2) 2 - pentene
1) H C 2) 3) 2 - pentyne
2
Br H 3C Br
4) 2 - methylbut - 2 - ene.
CH3 CH3
CH 3
3) 4) |
H2C Br H3C Br O ,CH 2Cl 2
Key; 4) CH 3  CH  C  CH 3 3  

CH3 +
HBr
- CH3 2 - methylbut - 2 - ene
Key: CH2 leq. CH2 Br

H2C H2C O
CH3 O
CH3 CH C Zn ||
CH3 CH3
 CH 3CHO  CH 3  C  CH 3
H 2O
CH 2Br O O Ethanal Propanone
H2C
20) Optically active compounds among the
17) The carbocation formed in SN1 reaction of alkyl following compounds are
halide in the slow step is i) 1 - Phenylethanol
1) sp3 - hybridised 2) sp2 - hybridised ii) 2 - Phenylpropan - 1 - ol
3) sp - hybridised 4) sp3d - hybridised. iii) 2 - Phenylpropan - 2 - ol
Key: 2) Carbocation formed in SN1 reaction is sp2 iv) 2 - Methylpropan - 2 - ol.
hybridised. 1) (ii) and (iii) 2) (i) and (ii)
3) (iii) and (iv) 4) (ii) and (iv)
18) The increasing order of reactivity in the SN2
hydrolysis of the following alkyl bromides is H
I) tert-Butyl bromide *
CH3CHOH H 3C - C - CH 2OH
II) Methyl bromide *
III) sec-Butyl bromide kEY: 2)
IV) n-Propyl bromide,
1 - Phenylethanol 2 - Phenylpropan - 1 - ol
1) (I)<(III)<(IV)<(II)
2) (II)<(IV)<(III)<(I) OH
3) (I)<(IV)<(III)<(II) CH 3
4) (II)<(III)<(IV)<(I) H3C - C - CH 3
|
kEY: 1) More bulky substractes are least reactive in H 3C  C  CH 3
|
SN2 reaction. OH
2 - Phenylpropan - 2 - ol 2  Methylpropan  2  ol
CH 3
|
0
CH 3  C 3  Br 21) Reactivity order of halides for
| CH3Br dehydrohalogenation is
CH 3 1) R - F > R - Cl > R - Br > R - I
2) R - I > R - Br > R - Cl > R - F
(tert - Butyl bromide) (Methyl bromide)
3) R - I > R - Cl > R - Br > R - F
4
 4) R - F > R - I > R - Br > R - Cl 25) For SN1 reaction, the order of reactivity-of
Key: 2) As the size of halide ion increases the R - X haloalkanes is
bond strength decreases and then the halide ion 1) tertiary halide < secondary halide < primary
will be a good leaving group. Thus, the halide
reactivity order towards dehydrohalogenation 2) tertiary halide < secondary halide > primary
is : halide
R - I > R - Br > R - Cl > R - F. 3) tertiary halide > secondary halide > primary
halide
22) Br + Mg  H 2O 4) tertiary halide > secondary halide < primary
 A 
Dry ether  B
H halide.
The product ‘B’ is Key: 3) SN1 reaction is two steps reaction in which
carbocation is formed as an intermediate in step
1) MgBr 2) OH
I (rate determining step). Greater the stability of
carbocation, greater will be its ease of formation
3) OH 4) from alkyl halide and faster will be the rate of
reaction. Thus, the order of reactivity of
Key: 4) Br + Mg 
Dry ether
 MgBr haloalkanes towards SN1 reaction is :
Tertiary halide > Secondary halide > Primary
halide.

26) The correct decreasing order of reactivity for a

+ Mg (OH) Br given alkyl (R) group in both SN1 and SN2
Cyclohexane reaction mechanisms is
‘B’ 1) R - I > R - Br > R - Cl > R - F
2) R - 1 > R - C > R - Br > R - F
23) Which of the following haloalkanes wouldH 0 3) R - F > R - Cl > R - Br > R - I
undergo SN2 reaction faster? 4) R - F > R - I > R - Cl > R - Br
Key: 1) Smaller the energy required for cleaving C -
I) CH2Cl II) Cl X bond, better is the leavinggroup and faster is
the rate of reaction. If ‘R’ is a bulky group, then
III) IV)
I Cl it is SN1 reaction otherwise SN2.
1) I 2) II
R - I > R - Br > R - Cl > R - F
3) III 4) IV
(most (least
Key: 3) Among I and II, I will undergo SN2 reaction reactive) reactive)
faster as it is a primary alkyl halide while II is a
secondary alkyl halide. Among I, III and IV, III C - X bond strength increases
will undergo SN2 reaction fastest as iodine is a
better leaving group because of large size and 27) Whcih of the following pairs are correctly
compound is primary alkyl halide. matched?
Reactants Products
24) The reaction,
CH3CH2I + KOH(aq)  CH3CH2OH + KI I. RX + Ag(OH)(aq) RH
is classified as II. RX + AgCN(al3) RNC
1) electrophilic substitution III. RX + KCN(al3) RNC
2) nucleophilic substitution IV. RX + Na(ether) R-R
3) electrophilic addition 1) I alone 2) I and II
4) nucleophilic addition. 3) II and III 4) II and IV
Key:2) Alkyl halides are hydrolysed to corresponding Key: 4) R - X + AGCN(al3) RNC + AgX
alcohols by boiling with aqueous alkali 2R - X + 2Na  R - R + 2NaX
Ether

soloution (NaOH or KOH). This is nucleophilic

substitution reaction in which the attacking 28) A nucleophilic substitution reaction proceeds
nucleophile is OH. through SN1 mechanism. So, the reaction is
5
 *1) unimolecular
2) bimolecular The number of meso forms, m = 0
3) termolecular Total no. of optical isomers = a + m = 4 + 0 =
4) rate depends on concentration of incoming 4
nucleophile.
32) Consider the following bromides :
29) 2-bromobutane reacts with OH- in H2O to give Me Br
2-butanol by SN1. The reaction involves
A
1) retention in configuration
2) inversion in configuration Me
3) racemisation Br
4) mutarotation. B
Key: 3) SN1 reaction of optically active alkyl halides
is accompanied by racemisation. Me
Me
30) Identify B and D in the following sequence of Br
reactions. C

Conc. H2SO4
CH2 = CH2 A The correct order of SN1 reactivity is
1) A > B > C
D  H2O
2) B > C > A
PBr3 3) B > A > C
C B 4) O > B > A
1) Methanol and bromoethane Key: 2) SN1 reaction rate depends upo0n the stability
2) Ethyl hydrogen sulphate and alcoholic KOH of the carbocation, as carbocation formation is
3) Ethyl hydrogen sulphate and aqueous KOH the rate determing step. Compound (2), forms
4) Ethanol and alcoholic KOH a 20 allylic carbocation which is the most stable,
Key: 4) CH2 = CH  the next stable carbocation is formed from (3)
  CH3CH2HSO4
conc .H 2SO 4
which is a 20 carbocation (1) forms the least
stable 1 0 carbocation. Thus, the order of
reactivity is :
Me Me
CH3CH2Br PBr3
 CH3CH2OH
Me
(3) (2) Br > Br
(B) (C)
31) The maximum number of possible optical
isomers in 1 - bromo - 2 - methyl cyclobutane > Me Br
is
1) 4 2) 2 33) Following is the substitution reaction in which -
3) 8 4) 16 CN replaces - Cl.
Key:1) Structure of 1 - bromo - 2 - methylcyclobutane R-CI+ KCN   R - CN + KCl
is
(alcoholic)
3 4 To obtain, propanenitrile, R - Cl should be
1) chloroethane 2) 1 - chloropropane
2 1
Br
3) chloromethane 4) 2- chloropropane.
CH3
Key: 1) CH3CH2Cl + KCN   CH3CH2CN + KCl
This molecule cannot be divided into two equal
halves, i.e., the molecule has no symmetry and (Alcoholic) Propanenitrile
n is the number of asymmetric carbon atoms,
then the number of d - and l - forms,
a = 2n = 22 = 4

6
34) Alkyl halides undergoing substitution
nucleophilic bimolecular reaction involves
1) formation of carbocation Br
2) racemic mixture 1) 2)
*3)inversion of configuration Br
4) retention of configuration. Br

Br
35) Which of the following compounds does not Br
rotate the plane polarised light?
1) 2 - Chloropropanoic acid 3) 4)
2) 2 - Chlorobutane
3) 4 - Hydroxyheptane hv
Key 4) Br2  2 Br CH3
.
4) 2 - Chloro - 1 - deuteropropane
Key: 3) 4 - Hydroxyheptane, due to absence of
asymmetric carbon atom does not rotate the
CH3 H .
CH3
Br



+ HBr
plane polarised light.
Most stable
Br Intermediate
H
36) The chirality of the compound
H3C
C
Cl
is .
CH3
Br 
CH3
Br


*1) R 2) S
3) Z 4) E
40) Allene (C3H4) contains
37) Which among the following is a catalyst for the 1) one triple and two double bonds
preparation of Grignard reagent? 2) two double and four single bonds
1) Iron powder *2) Iodine powder 3) two triple and one double bonds
3) Activated charcoal 4) Manganese dioxide 4) one double and one triple bond.
Key 2) Allene, (C3H4) :
38) In the following structure, the double bonds are H2C = C = CH2
marked as I, II, III and IV: Double bonds = 2
II Single bonds = 4

III 41) The reaction of propene with HBr in presence

of peroxide proceeds through the intermediate
I IV

1) H 3C  CH  CH 3
Geometrical isomerism is not possible at site(s)

*1) I 2) III 2) H 3C  CH  CH 2Br
3) I and III 4) III and IV
Key 1) For geometrical isomerism, different groups Br
|
should be attached to each sp2 hybridised C- 3) H 3C  CH  CH 2
atom.

4) H 3C  CH 2  CH 2
39) The major product of the following reaction is

Br2 / hv
  

7
 O O CH 3
|| || | (i ) O 3 / CH 2Cl 2
Key 2) C 6H 5  C  O  O  C  C 6H 5 Key: 4) CH 3  C  CH 2 (ii 
) Zn/H 2O


Benzoyl peroxide 2 - methylpropene

O CH 3
||  |
CH 3  C  O  HCHO
2C 6H 5  C  O  2C 6H 5  CO 2


Phenyl Propane Methanal

. radical
C 6H 5  H  Br  C 6H 6  Br 
CH 3
| (i)O3 / CH 3Cl 2
   
(ii) Zn/H 2O
Propane (20 radical) H 3C  C  CH  CH 3
2 - Methylbut - 2 - ene
CH3CH - CH2Br + H - Br CH 3
CH3 - CH2 - CH2Br + Br |
1 - Bromopropane CH 3  C  O  CH 3CHO
Propanone Acetaldehyde
42) Which of the following is Baeyer’s reagent?
CH 3CH 3
1) Alkaline KMnO4 2) Acidic K2Cr2O7 | | (i)O3 / CH 3Cl 2
   
3) Alkaline Na2Cr2O7 4) MnO2 H 2C  C  CH  CH 3 (ii) Zn/H 2O

Key: 1) Baeyer’s reagent is alkaline solution of cold

2, 3 - Dimethylbut - 1 - ene
potassium permanganate3 (KMnO4)
CH3
HCHO + C=O
43) The reaction of propene with HOCl (Cl2+H2O)
proceeds through the intermediate : CH3 - CH
1) CH3 - CH - CH2 - OH CH3
2) CH3 - CH(OH) - CH2 - Cl
3) CH3 - CH(OH) - CH2
3 - Methylbutan - 2 - one
4) CH3- CHCl - CH2
Key: 2) HOCl OH- + Cl+
CH3 CH3 (i)O3 / CH 3Cl 2
Cl+ CH3 - C H - CH2 - Cl C=C    
CH 3 - CH = CH 2 CH3 CH3 (ii) Zn/H 2O

CH 3  CH  CH 2  Cl 2, 3 - Dimethylbut - 2 - ene
OH 
 | CH3 CH3
OH C=O + C=O
CH3 CH3
44) Which one of the following alkenes on Propanone (Two molecules)
hydrogenation produces an optically active
product? 46) When 2-bromopentane is heated with alcoholic
1) 2 - Methylbut - 2 - ene solution of potassium hydroxide, the major
*2) 3 - Methylhex - 3 - ene product obtained is
3) 2 - Methylpent - 2 - ene 1) pent-1-ene 2) pent-2-ene
4) 3 - Methylpent - 2 - ene 3) pent-1-yne 4) pent-2-yne,
KeY: 2) According to Saytzeff rule, in
45) Which among the following alkenes on dehydrohalogenation reactions, the preferred
reductive ozonolysis produces only propanone? product is that alkene which has the greater
1) 2 - Methylpropene number of alkyl groups attached to the doubly
2) 2 - methylbut - 2 - ene bonded carbon atoms. Thus, 2 - bromopentane
3) 2, 3 - Dimethylbut - 1 - ene gives pent - 2 - ene as the major product.
4) 2, 3 - Dimethylbut - 2 - ene

8
 50) In the given reaction, A may be
47) Anti-Markovnikov addition of HBr is observed
H 2O CH3
in A H 
2 SO4
1) propene 2) but-2-ene OH
3) pent-2-ene 4) all of these. CH3 CH3
Key: 1) Anti-Markovnikov addition is observed in
unsymmetrical alkenes like propene in presence 1) 2)
ol peroxide.

48) Ethylene can be converted into alcohol by

treatment of 3) 4)
1) aq.KOH 2) H2SO4 as catalyst
3) moist silver oxide 4) Zn/HCl.
Key: 2) In the presence of a few drops of cone. H2SO4 CH2
ethylene reacts with water to form ethyl alcohol, H 2O CH3
in accordance with Markovnikov rule. Key: 3) 
H 2 SO4
Methylene OH
CH 2 CH 3 CH 3 cyclohexane
H2O
|| +H SO  |  | + (A)
2 4
CH 2 CH 3HSO 4 Boil CH 2OH

H2SO4

49) The products obtained by the ozonolysis of 2 -

ethylbut - 1 - ene are
1) propanone and ethanal
2) ethanal and 3 - pentanone
3) butanal and ethanal
4) methanal and 3 - pentanone.
i ) O 3 (Ozonolysi s)
Key: 4) H 3C  CH 2  C  CH 2    
| ii) Zn/H 2O
CH 2CH 3
2 - Ethylbut - 1 - ene
O
||
HCHO  H 3C  CH 2  C  CH 2  CH 3
Methanal 3 - Pentanone