24-26

Chemistry (NEET)

Hints to HDA Date : 25/06/2025

1. (1)
2. (2) In vinylic halide, H-atom is bonded to an sp2-hybridized carbon atom of carbon-carbon double bond.

I CH3 CH3 CH3

| | 1 | 1 | 1
3. (1) CH3 – CH  CH3 CH3 – CH  CH2  CH2I CH3 – CH  CH2I CH3 – CH  CH 2I
2 Isopentyliodide Isobutyliodide |
Isopropyliodide CH3
Neopentyl iodide
4. (2) According to IUPAC rule: 1-Chloro-2, 2-dimethylpropane:
CH3
3 2| 1
CH3 – CH  CH2  Cl
|
CH3

5. (3) Isomers have same molecular formula. Hence, they cannot be homologue (homologue have the
difference of 14 in their molecular weight). Optically active compounds may exist in four forms viz.
dextro, leavo, racemic and meso compounds.
6. (4) When alkyl halide reacts with alc. KOH then it favours elimination reaction (Dehydrohalogenation).
Since, trans pent-2-ene is more symmetrical than cis isomer. Hence, it is main product.
Br
| KOH(alc.)
CH2  CH3
CH3  CH CH2  CH2  CH3 
Dehydrohalogenation
 CH  CH
2-Bromopentane CH3
trans-Pent-2-ene
7. (1) Chlorination of 2, 2, 5, 5-tetramethylhexane can give three isomeric monochloro derivatives.
CH3 CH3 CH3 CH3 CH3 CH3
| | | | | |
Cl2 /hν
CH3  C  CH2  CH2  C  CH3   CH2  C  CH2  CH2  C  CH3  CH3  C  *CH  CH2  C  CH3
| | | | | | | |
CH3 CH3 Cl CH3 CH3 CH3 Cl CH3
2, 2, 5, 5-Tetramethylhexane 2 Sterioisomers (  )

8. (4) Chlorobenzene can be prepared by reacting aniline with nitrous acid followed by heating with cuprous
chloride.
NH2 N2Cl Cl

0-5°C Cu / HCl, 
+ NaNO2 + 2HCl    
– 2H O, – NaCl
2 
Gattermann reaction
9. (1) Boiling point increases with the increase in molecular weight. For a given alkyl group, alkyl iodides
have the highest molecular weight.
10. (1) Both the compounds form same product on treatment with alcoholic KOH. KOH show elimination
reaction and ethyne as the product.
Ethylene chloride Ethylidene chloride
KOH KOH
(alc)
CH3  CHCl2   CH  CH (alc)
CH2Cl  CH2Cl   CH  CH
KOH KOH
(2) CH3CHCl2  (aq)
 CH3CHO CH2Cl  CH2Cl  (aq)
 HOCH2  CH2OH
Acetaldehyde Ethylene glycol
Zn dust Zn dust
(3) CH3CHCl2   CH  CH CH2Cl  CH2Cl   CH  CH
(4) Ethylene chloride and ethylidene chloride both are optically inactive.
11. (2) Transition state is the state in between initial and final state of a reaction. It has high energy content
and is very unstable hence reaches to final state.
12. (1) The complete reaction is as follows:
Cl ⊕ + CH2 = CH2  CH2 – CH2 – Cl ≡
Cl
⊖ ⊕
AlCl3 – Cl
13. (1) It is Fittig reaction.
Br

2
Bromobenzene Diphenyl
14. (1) Alkaline hydrolysis of tertiary butyl bromide follows SN1 mechanism.
 Rate of reaction  [(CH3)3 C – Br]
 Rate is doubled if the concentration of alkyl halide is doubled. In SN1 mechanism, reaction rate does
not depend on the concentration of nucleophile.
15. (2) Vinyl chloride does not readily react with sodium hydroxide (NaOH) due to the high stability of the
(C – Cl) bond in vinyl chloride. This is because the C – Cl bond acquires some double bond character
due to resonance, making it very difficult to break. Ethyl chloride produces alcohol on aqueous
hydrolysis and then alcoholic AgNO3 gives white ppt. of AgCl as follows:
KOH
(aq) AgNO3
C2H5 – Cl   C2H5 – OH + Cl⊕   AgCl
ZnCl2/HCl (Lucas regent), AgCl and HCl/AgCl will not react with both.
16. (1) The stereoisomers related to each other are non-superimposable on their mirror images. Such isomers
are called enantiomers. Enantiomer of molecule (P) because in this, the configuration of two groups,
i.e., CH3 and C2H5 is reversed at the chiral carbon.
17. (3) Due to resonance it is shorter but stronger.
18. (1) Primary alkyl halide readily undergoes SN2 reaction. (4) is tertiary alkyl halide and (3) and (2) are
secondary alkyl halides form carbocation, preferably undergo SN1 reaction.
19. (4) Sulphonation of chlorobenzene gives 4-chlorobenzene sulphonic acid as major product.
Cl Cl Cl
SO3H
+
2-Chlorobenzene SO3H
sulphonic acid 4-Chlorobenzene
(Minor) sulphonic acid (Major)
20. (2) Reaction of alkanes with fluorine is explosive hence direct fluorination method is not used. HF is
poisonous and corrosive hence R – F is not prepared by the action HF on alkene. It is prepared by
Swarts reaction which is a halogen exchange reaction.
R – Cl/Br + AgF  R – F + AgCl/Br
21. (4)
22. (4) First step is free radical chlorination and 2nd is hydrolysis of dichloro alkylarene which finally gives
p-Chlorobenzaldehyde.
OH
CH3 CHCl2 CH CHO
OH

Cl Cl Cl Cl
Unstable p-Chlorobenzaldehyde
23. (4) Grignard reagents react with compounds containing active hydrogen atoms (viz. water, alcohols,
amines etc.) to form alkanes corresponding to the alkyl group of the Grignard reagent.
CH3OH CH3NH2 H2O
C2H5MgBr 
Mg(OCH )Br
 C2H6; C2H5MgBr 
Mg(NH)Br
 C2H6; C2H5MgBr 
Mg(OH)Br
 C2H6
3

24. (1) Acute chloroform intoxication can cause depression of the central nervous system and may lead to
death from lethal arrhythmias or respiratory arrest. Thus, the organic solvent is no longer in clinical
use as an anaesthetic.
25. (3) Haloarenes are o and p-directing hence (a) and (c) can give three isomers.
26. (1) Addition of HBr to 1− butene gives two optical isomers as the product contains one asymmetric carbon.
Br
|
*
CH3 – CH2 – CH = CH2 + HBr  CH3  CH2  CH CH3
2-Bromobutane
Number of optical isomers = 2n = 21 = 2
27. (4) –Cl is o- and p–directing group.
Cl Cl Cl
NO2
+
o-Nitrochlorobenzene
NO2
p-Nitrochlorobenzene

28. (1) The addition of HBr to symmetrical alkenes (2-butene) is not affected by the presence or absence of
peroxide.
H2O2
H3C – CH = CH – CH3 + HBr   CH3 – CH2 – CHBr  CH3 or CH3  CHBr  CH2  CH3
2-Butene 2-Bromobutane 2-Bromobutane
29. (3) The order of reactivity of alkyl halides towards SN2 reactions is 1 > 2 > 3. Thus compounds (I) being a
3 alkyl halide is least reactive.
Out of 1 alkyl halides II and IV due to large size and lower Electronegativity of I– ion it is better leaving
group than Cl– ion. Therefore the correct order of reacting towards SN2 reaction is I < III < IV < II.
30. (3) 1st reaction is dehydrohalogenation and then bromination. A and C are position isomer.
Br
CH2Br
Br Br Br
(A) (B) (C)

31. (3) a = 2n, a = 23 = 8, Where; a = number of optical isomers, n = number of asymmetric carbon atoms.
32. (1) In the laboratory, addition of bromine in CCl4 to an alkene resulting in discharge of reddish-brown
colour of bromine constitutes an important method for the detection of double bond in a molecule. The
addition results in the synthesis of vic-dibromides, which are colourless.
H H Br H
CCl4
CC  Br2   CC
H H H Br
Alkene vic-Dibromide

33. (2) FeCl3 + Cl2  FeCl 4 + Cl+ (electrophile)

34. (1) o-Chloroacetophenone will be the minor product when chlorobenzene is treatment with acetyl chloride
and anhydrous AlCl3.
Cl Cl Cl
COCH3
+
Chlorobenze o-Chloroacetophenone COCH3
ne Minor p- Chloroacetophenone
Major
35. (3) Attack on 3rd carbon atom will make the compound chiral.
X
1 2 3 4 5 6 7 1 2| 3 4 5 6 7
X
CH3  CH2  CH2  CH2  CH2  CH2  CH3 
H
CH3  CH2  CH  CH2  CH2  CH2  CH3

36. (1) The melting point of isomeric dihalobenzenes the para-isomer is high as compared to the ortho and
meta-isomers because the para-isomer is more symmetrical than the ortho and meta-isomers.
dry ether
37. (3) C2H5I + C3H7I + Na   C2H5  C3H7 + NaI
Pentane
dry ether
2C2H5I + Na  C2H5  C2H5 + NaI
Butane
dry ether
2C3H7I + Na  C3H7  C3H7 + NaI
Hexane
38. (4) Combination of two free radicals may be chain terminating step, if the free radicals combine amongst
themselves without giving rise to any new radicals.
39. (4) Electron withdrawing groups are highly ineffective at meta position in nucleophilic aromatic
substitution reactions. Hence, compound (4) will have lowest rate in nucleophilic aromatic
substitution.
Δ
40. (3) H3C – CH2 – CH2Cl + KCN  H3C – CH2 – CH2 – CN + KCl
Propyl chloride Butanenitrile or n-propyl cyanide
41. (4) Thionyl chloride is preferred over PCl3 and PCI5 for the preparation of alkyl chlorides from alcohols,
because thionyl chloride gives pure alkyl halide as other two products (SO2+HCl) are escapable gases.
42. (1) Reactivity of alkyl halides towards SN1 reactions decreases in the order: 3 > 2 > 1 > +CH3
and of halogen is: I > Br > Cl.
Cl
In the given question is 2 halide whereas others are 3-halides.
 ,anhy.ZnCl2
43. (4) Alcohol + HCl   Alkyl halide + H2O.

ether
44. (1) CH3 – CH2 – Br + Mg   CH3CH2MgBr
This is the method of preparation of Grignard reagent. Dialkyl Magnesium is not formed in this
reaction. Formation of ethers requires sodium alkoxide and alkyl halide. Ethyl alcohol is formed when
ethyl bromide hydrolysed in aq. KOH

45. (2)