Organic Compounds Containing Halogens — DPP 3

20 NEET questions from Organic Compounds Containing Halogens, with answers and explanations. Attempt it as a timed test to get scoring, accuracy breakdown and mistake tracking.

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1
Which among the following is Darzen's method of preparation of alkyl chloride?
  1. A $\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{OH} \xrightarrow{\mathrm{PCl}_{5}} \mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{Cl}$
  2. B $\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{OH} \xrightarrow[\mathrm{ZnCl}_{2}]{\mathrm{HCl}} \mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{Cl}$
  3. C $\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{OH} \xrightarrow{\mathrm{PCl}_{3}} \mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{Cl}$
  4. D $\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{OH} \xrightarrow{\mathrm{SOCl}_{2}} \mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{Cl}$
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Correct answer: D

$\mathrm{R}-\mathrm{OH} \xrightarrow[\text { (Darzen's method) }]{\mathrm{SOCl}_{2}} \mathrm{RCl}+\mathrm{SO}_{2}+\mathrm{HCl}$
2
Which among the following is the correct order of melting point?
  1. A
  2. B
  3. C
  4. D
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Correct answer: C

The correct order of melting point is
Organic Compounds Containing Halogens – NEET-15339 This is because of more symmetrical structure and tight crystal packing.
3
Enantiomers are chiral molecules
  1. A Superimposable mirror image
  2. B Non-superimposable mirror images
  3. C Symmetric molecules
  4. D Achiral molecules
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Correct answer: B

Enantiomers are chiral molecules
4
Which one of the following is gem-dihalide?
  1. A $\mathrm { CH } _ { 3 } \mathrm { CHBr } _ { 2 }$
  2. B $\mathrm { CH } _ { 2 } \mathrm { Br } - \mathrm { CH } _ { 2 } \mathrm { Br }$
  3. C $\mathrm { CH } _ { 3 } \mathrm { CHBrCH } _ { 2 } \mathrm { Br }$
  4. D $\mathrm { CH } _ { 3 } \mathrm { CHBrCH } _ { 2 } \mathrm { CH } _ { 2 } \mathrm { Br }$
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Correct answer: A

Organic Compounds Containing Halogens – NEET-15302
5
The reaction goes through
  1. A S$_ \mathrm { N }$1
  2. B $\mathrm { S } _ { \mathrm { N } } 2$
  3. C E$_ { 2 }$
  4. D E$_ { 1 }$
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Correct answer: B

Organic Compounds Containing Halogens – NEET-15274
6
Which of the following is the least volatile?
  1. A $\mathrm { CH } _ { 3 } - \mathrm { CH } _ { 2 } - \mathrm { CH } _ { 2 } - \mathrm { F }$
  2. B $\mathrm { CH } _ { 3 } - \mathrm { CH } _ { 2 } - \mathrm { CH } _ { 2 } - \mathrm { Cl }$
  3. C
  4. D $\mathrm { CH } _ { 3 } - \mathrm { CH } _ { 2 } - \mathrm { CH } _ { 2 } - \mathrm { Br }$
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Correct answer: D

B.P. $\propto$ size of molecule
∵ of van der Waal's force of attraction.
Among the following
Organic Compounds Containing Halogens – NEET-15337 has highest boiling point.
Also, V.P $\propto \frac{1}{\text { B.P }}$
Hence, smaller the V.P (Vapour pressure) lower will be volatility.
7
For the given alkyl halides $\mathrm { CH } _ { 3 } - \mathrm { F } , \mathrm { CH } _ { 3 } - \mathrm { Cl }$, $\mathrm { CH } _ { 3 } - \mathrm { Br }$ and $\mathrm { CH } _ { 3 } - \mathrm { I }$ the correct order of reactivity towards $\mathrm { S } _ { \mathrm { N } } 2$ reaction is
  1. A $\mathrm { CH } _ { 3 } - \mathrm { F } > \mathrm { CH } _ { 3 } - \mathrm { Cl } > \mathrm { CH } _ { 3 } - \mathrm { Br } > \mathrm { CH } _ { 3 } - \mathrm { I }$
  2. B $\mathrm { CH } _ { 3 } - \mathrm { Cl } > \mathrm { CH } _ { 3 } - \mathrm { F } > \mathrm { CH } _ { 3 } - \mathrm { Br } > \mathrm { CH } _ { 3 } - \mathrm { I }$
  3. C $\mathrm { CH } _ { 3 } - \mathrm { I } > \mathrm { CH } _ { 3 } - \mathrm { Cl } > \mathrm { CH } _ { 3 } - \mathrm { Br } > \mathrm { CH } _ { 3 } - \mathrm { F }$
  4. D $\mathrm { CH } _ { 3 } - \mathrm { I } > \mathrm { CH } _ { 3 } - \mathrm { Br } > \mathrm { CH } _ { 3 } - \mathrm { Cl } > \mathrm { CH } _ { 3 } - \mathrm { F }$
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Correct answer: D

Leaving ability order : $\mathrm{I}>\mathrm{Br}>\mathrm{Cl}>\mathrm{F}$
8
The correct reagent that gives vic-dibromide on reaction with but-2-ene is [NCERT Pg. 165]
  1. A NBS
  2. B $\mathrm { Cu } _ { 2 } \mathrm { Br } _ { 2 }$
  3. C HBr
  4. D $\mathrm { Br } _ { 2 } / \mathrm { CCl } _ { 4 }$
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Correct answer: D

Organic Compounds Containing Halogens – NEET-15325
9
Which one is the most reactive towards $\mathrm { S } _ { \mathrm { N } } 1$ reaction?
  1. A $\mathrm { Ph } - \mathrm { CH } _ { 2 } - \mathrm { Br }$
  2. B
  3. C
  4. D
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Correct answer: D

Organic Compounds Containing Halogens – NEET-15225 This is most reactive for S$_{N}$1 reaction amongst the choices given.
Organic Compounds Containing Halogens – NEET-15225 Here, 3 Hyperconjugating and 6 Resonating structures are plausible to stabilizers this carbocation.

10
$\left( \mathrm { p } - \mathrm { ClC } _ { 6 } \mathrm { H } _ { 4 } \right) _ { 2 } \mathrm { CHCCl } _ { 3 }$ is used as a/an
  1. A Antiseptic for wounds
  2. B Insecticide
  3. C Pyrene
  4. D Refrigerant
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Correct answer: B

Organic Compounds Containing Halogens – NEET-15300
11
Replacement of Cl of chloro-benzene to give phenol requires drastic conditions. But chlorine of 2, 4-dinitro-chloro-benzene is readily replaced
  1. A $\mathrm { NO } _ { 2 }$ donates electron at meta position
  2. B $\mathrm { NO } _ { 2 }$ withdraws electron from ortho/para positions
  3. C $\mathrm { NO } _ { 2 }$ make ring electron rich at ortho & para
  4. D $\mathrm { NO } _ { 2 }$ withdraws electron from meta position
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Correct answer: B

This is again ArSN reaction. The intermediate of this reaction is carbanion, whose stability can be increase by electron withdrawing group like $-\mathrm{NO}_{2}$.
12
For $\mathrm { S } _ { \mathrm { N } } 1$ mechanism, which of the following is correct?
  1. A Inversion (100%)
  2. B Formation of carbocation
  3. C Non-polar solvent
  4. D Elimination
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Correct answer: B

In $\mathrm{S}_{\mathrm{N}} 1$ mechanism, $\mathrm{C}^{+}$formation in R.D.S. (Slow step)
13
Organic Compounds Containing Halogens – NEET-15379 What is B?
  1. A
  2. B
  3. C
  4. D
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Correct answer: D

Organic Compounds Containing Halogens – NEET-15379
14
Organic Compounds Containing Halogens – NEET-15404 For which of the following G , above reaction will be the fastest?
  1. A -OH
  2. B -CH$_{3}$
  3. C -NO$_{2}$
  4. D -CHO
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Correct answer: C

Organic Compounds Containing Halogens – NEET-15404 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.
15
Swart's reaction is used for the preparation of
  1. A $\mathrm { CH } _ { 3 } - \mathrm { Cl }$
  2. B $\mathrm { CH } _ { 3 } - \mathrm { Br }$
  3. C $\mathrm { CH } _ { 3 } - \mathrm { I }$
  4. D $\mathrm { CH } _ { 3 } - \mathrm { F }$
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Correct answer: D

Swarts reaction is used for the synthesis of alkyl fluorides.
16
When 3-phenylprop-1-ene is treated with HBr in presence of peroxide then the major product of the reaction among the following is
  1. A
  2. B
  3. C
  4. D
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Correct answer: A

Organic Compounds Containing Halogens – NEET-15315
17
The reaction of toluene with $\mathrm { Cl } _ { 2 }$ in presence of $\mathrm { FeCl } _ { 3 }$ gives X and reaction in presence of light gives Y. Thus, X and Y are
  1. A X = Benzyl chloride, Y = m-chlorotoluene
  2. B X = Benzal chloride, Y = 0-chlorotoluene
  3. C X = m-chlorotoluene, Y = p-chlorotoluene
  4. D X = 0 - and p-chlorotoluene, Y = Trichloromethyl benzene
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Correct answer: D

Organic Compounds Containing Halogens – NEET-15336
18
Organic Compounds Containing Halogens – NEET-15401 Product (D) in the reaction is
  1. A Optically active cyanide
  2. B Optically inactive acid
  3. C Optically active acid
  4. D Optically active aldehyde
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Correct answer: B

Organic Compounds Containing Halogens – NEET-15401
19
The incorrect statement among the following is
  1. A Chiral molecules are optically active
  2. B Achiral molecules are optically inactive
  3. C Enantiomers have same refrective index
  4. D Enantiomers have different melting point
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Correct answer: D

Enantiomers have same melting point.
20
Best reagent for converting an alcohol into corresponding chloride is
  1. A $\mathrm { HCl } / \mathrm { ZnCl } _ { 2 }$
  2. B $\mathrm { PCl } _ { 3 }$
  3. C $\mathrm { PCl } _ { 5 }$
  4. D $\mathrm { SOCl } _ { 2 }$
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Correct answer: D

$\mathrm{R}-\mathrm{OH}+\mathrm{SOCl}_{2} \longrightarrow \mathrm{R}-\mathrm{Cl}+\mathrm{SO}_{2}(\uparrow)+\mathrm{HCl}(\uparrow)$

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