${{\rm{C}}_6}{{\rm{H}}_5}{\rm{Cl}}$ on treating with ${\rm{NaOH}}$ at $300^\circ C$ gives phenol. However the yield is poor because of side reaction producing:

${{\rm{C}}_6}{{\rm{H}}_5}{\rm{O}}{{\rm{C}}_6}{{\rm{H}}_5}$

${{\rm{C}}_6}{{\rm{H}}_5}{\rm{Na}}$

${{\rm{C}}_6}{{\rm{H}}_5}{\rm{OC}}{{\rm{H}}_3}$

$C{H_3} - CH - C{H_2} - C{H_3}\xrightarrow[{UV}]{{C{l_2}}}A\,\left( {{\rm{major}}} \right),\,A$ is

$C{H_3} - \mathop {CH}\limits^{\mathop |\limits^{C{H_3}} } - \mathop {CH}\limits_{\mathop |\limits_{Cl} } - C{H_3}$

$C{H_3} - \mathop C\limits^{\mathop |\limits^{C{H_3}} } - C{H_2} - C{H_2}Cl$

$C{H_3} - \mathop {CH}\limits^{\mathop |\limits^{C{H_3}Cl} } - C{H_2} - C{H_3}$

The ${\rm{CC}}{{\rm{l}}_4}$ and ${\rm{CHC}}{{\rm{l}}_3}\;$ can be distinguished by the action of:

$R{\rm{N}}{{\rm{H}}_2} + {\rm{KOH\;alc}}.$

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NEET • CHEMISTRY • HALOALKANES AND HALO ARENES

Haloalkanes and halo arenes practice · Medium

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1 Medium

1 of 45

Remembering +4 | -1

Which of the following compounds is an example of Freon?

View answer and explanation

Correct option: D

\mathrm{C}_2 \mathrm{Cl}_2 \mathrm{~F}_2

Option D (

\mathrm{C}_2 \mathrm{Cl}_2 \mathrm{~F}_2

) is correct because Freons are chlorofluorocarbons (CFCs) or hydrochlorofluorocarbons (HCFCs).

2 Medium

2 of 45

Analyzing +4 | -1

Which one of the following is most reactive towards aqueous

NaOH

View answer and explanation

Correct option: B

{\mathrm{C}_6}{\mathrm{H}_5}\mathrm{C}{\mathrm{H}_2}\mathrm{Cl}

Option B (

{\mathrm{C}_6}{\mathrm{H}_5}\mathrm{C}{\mathrm{H}_2}\mathrm{Cl}

) is correct because the chlorine atom is attached to a benzylic carbon, making it more susceptible to nucleophilic substitution reactions.

3 Medium

3 of 45

Analyzing +4 | -1

Which process does not occur during formation of

\mathrm{CHC}{\mathrm{l}_3}\mathrm{\;from\;\;}{\mathrm{C}_2}{\mathrm{H}_5}\mathrm{OH\;and\;bleaching}\;

powder?

View answer and explanation

Correct option: C

Elimination

Option C (Elimination) is correct because elimination reactions are not involved in the formation of chloroform from ethanol and bleaching powder.

4 Medium

4 of 45

Application +4 | -1

Which of the following reaction(s) can be used for the preparation of alkyl halides?

i)

C{H_3}C{H_2}OH + HCl\xrightarrow{{\mathrm{Anhyd}\mathrm{.ZnC}{\mathrm{l}_2}}}

ii)

C{H_3}C{H_2}OH + HCl \to

iii)

{(C{H_3})_3}COH + HCl \to

iv)

{(C{H_3})_2}CHOH + HCl\xrightarrow{{\mathrm{Anhyd}\mathrm{.ZnC}{\mathrm{l}_2}}}

View answer and explanation

Correct option: C

I, III and IV only

Option C (I, III and IV only) is correct because primary, secondary, and tertiary alcohols can react with HCl to form alkyl halides, sometimes requiring a catalyst like anhydrous

ZnCl_2

5 Medium

5 of 45

Understanding +4 | -1

Isobutyl chloride and butyl chloride are:

View answer and explanation

Correct option: B

Chain isomers

Option B (Chain isomers) is correct because isobutyl chloride and butyl chloride have the same molecular formula but differ in the arrangement of the carbon chain.

6 Medium

6 of 45

Analyzing +4 | -1

Read the following statements
A. Gabriel phthalimide synthesis is used to prepare all

{1^0}

amines
B.

{C_6}{H_5}Cl{C_6}{H_5} - {C_6}{H_5}

is known as Wurtz reaction.
C. In

S{N^1}

mechanism there is more inversion than retention leading to partial racemization
D. All aldehydes give red precipitate with Fehling’s solution
E. Reactivity order of alkyl halides towards

S{N^2}

reaction is

{1^0} > {2^0} > {3^0}

Number of correct statements among these

View answer and explanation

Correct option: A

Option A is correct because only statements C and E are correct. Gabriel synthesis gives only primary amines, Wurtz reaction is different, aldehydes don't always give red precipitate.

7 Medium

7 of 45

Application +4 | -1

Identify Z in

C{H_3}C{H_2}C{H_2}Br\xrightarrow{{Ag.NaOH}}X\xrightarrow[\Delta ]{{A{l_2}{O_3}}}Y\xrightarrow{{C{l_2}/{H_2}O}}Z

View answer and explanation

Correct option: B

C{H_3}CHOHC{H_2}Cl

Option B (

C{H_3}CHOHC{H_2}Cl

) is correct because the sequence of reactions leads to the formation of 1-chloropropan-2-ol.

8 Medium

8 of 45

Application +4 | -1

Sodium ethoxide reacts with ethyl iodide to yield:

View answer and explanation

Correct option: C

{\mathrm{C}_2}{\mathrm{H}_5}\mathrm{O}{\mathrm{C}_2}{\mathrm{H}_5}

Option C (

{\mathrm{C}_2}{\mathrm{H}_5}\mathrm{O}{\mathrm{C}_2}{\mathrm{H}_5}

) is correct because sodium ethoxide reacts with ethyl iodide via Williamson ether synthesis to form diethyl ether.

9 Medium

9 of 45

Remembering +4 | -1

Alkyl fluorides are synthesised by alkyl chloride/bromide in presence of ____ or ____

i)

Ca{F_2}

ii)

Co{F_2}

iii)

H{g_2}{F_2}

iv) NaF

View answer and explanation

Correct option: B

ii,iii

Option B (ii,iii) is correct because alkyl fluorides are synthesized from alkyl chlorides/bromides using heavy metal fluorides like

CoF_2

and

Hg_2F_2

in Swarts reaction.

10 Medium

10 of 45

Analyzing +4 | -1

Which of the following are arranged in decreasing order of dipole moment:

View answer and explanation

Correct option: B

\mathrm{C}{\mathrm{H}_3}\mathrm{Cl},\mathrm{\;C}{\mathrm{H}_3}\mathrm{F},\mathrm{\;C}{\mathrm{H}_3}\mathrm{Br}

Option B is correct because dipole moment depends on both electronegativity difference and bond length. Although F is more electronegative than Cl, the C-Cl bond is longer, resulting in a higher dipole moment for CH3Cl.

11 Medium

11 of 45

Remembering +4 | -1

Which of the following represents Westrosol ?

View answer and explanation

Correct option: D

CC{l_2} = CHCl

Option D (

CC{l_2} = CHCl

) is correct because Westrosol is the common name for trichloroethylene, which has the formula

CC{l_2} = CHCl

12 Medium

12 of 45

Remembering +4 | -1

Alkali metals readily dissolve in liquid ammonia to give blue coloured solutions. The blue colour is believed to be due to

View answer and explanation

Correct option: C

ammoniated electrons

The correct answer is ammoniated electrons because the blue color in alkali metal-ammonia solutions arises from solvated electrons.

13 Medium

13 of 45

Remembering +4 | -1

Methyl ketone is identified by

View answer and explanation

Correct option: A

Iodoform test

Option A (Iodoform test) is correct because methyl ketones give a positive iodoform test, producing a yellow precipitate of iodoform (

CHI_3

14 Medium

14 of 45

Analyzing +4 | -1

{\mathrm{C}_6}{\mathrm{H}_5}\mathrm{Cl}

on treating with

\mathrm{NaOH}

300^\circ C

gives phenol. However the yield is poor because of side reaction producing:

View answer and explanation

Correct option: C

{\mathrm{C}_6}{\mathrm{H}_5}\mathrm{O}{\mathrm{C}_6}{\mathrm{H}_5}

Option C (

{\mathrm{C}_6}{\mathrm{H}_5}\mathrm{O}{\mathrm{C}_6}{\mathrm{H}_5}

) is correct because diphenyl ether is formed as a side product due to the reaction of phenoxide ion with chlorobenzene.

15 Medium

15 of 45

Remembering +4 | -1

General formula for arenes is:

View answer and explanation

Correct option: D

{\mathrm{C}_n}{\mathrm{H}_{2n - 6y}}

Option D (

{\mathrm{C}_n}{\mathrm{H}_{2n - 6y}}

) is correct because arenes contain benzene rings, and the general formula accounts for the unsaturation caused by the rings, where 'y' represents the number of benzene rings.

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16 Medium

16 of 45

Analyzing +4 | -1

Assertion : 4-Nitrochlorobenzene undergoes nucleophilic substitution more readily than chlorobenzene.

Reason : Chlorobenzene undergoes nucleophilic substitution by elimination-addition mechanism while 4-nitrochlorobenzene undergoes nucleophilic substitution by addition-elimination mechanism.

View answer and explanation

Correct option: B

If both Assertion and Reason are correct, but Reason is not the correct explanation of Assertion.

Option B (If both Assertion and Reason are correct, but Reason is not the correct explanation of Assertion) is correct because while both statements are true, the reason provided doesn't accurately explain the enhanced reactivity of 4-nitrochlorobenzene.

17 Medium

17 of 45

Application +4 | -1

1-phenyl, 2-chloropropane on treatment with aqueous

\mathrm{KOH}

gives mainly:

View answer and explanation

Correct option: C

1-phenylpropan-2-ol

Option C (1-phenylpropan-2-ol) is correct because the reaction of 1-phenyl, 2-chloropropane with aqueous KOH results in a nucleophilic substitution (

SN_1

SN_2

) where the chlorine atom is replaced by a hydroxyl group at the 2nd carbon.

18 Medium

18 of 45

Application +4 | -1

At higher temperature, iodoform reaction is given by:

View answer and explanation

Correct option: B

\mathrm{C}{\mathrm{H}_3}\mathrm{COO}{\mathrm{C}_2}{\mathrm{H}_5}

Option B (

\mathrm{C}{\mathrm{H}_3}\mathrm{COO}{\mathrm{C}_2}{\mathrm{H}_5}

) is correct because esters with the structure

CH_3COOR

RCOCH_3

give a positive iodoform test at higher temperatures.

19 Medium

19 of 45

Understanding +4 | -1

Although chlorobenzene does not give Ulmann’s reaction. However, presence of…group in chlorobenzene at

o - ,p -

position enables it to give Ulmann’s reaction.

View answer and explanation

Correct option: A

\mathrm{N}{\mathrm{O}_2}

Option A (

\mathrm{N}{\mathrm{O}_2}

) is correct because the presence of a nitro group at the ortho- or para- position activates chlorobenzene towards nucleophilic substitution reactions like the Ullmann reaction.

20 Medium

20 of 45

Analyzing +4 | -1

2-chlorobutane obtained by chlorination of butane, will be:

View answer and explanation

Correct option: B

Racemic form

Option B is correct because chlorination of butane at the 2nd carbon creates a chiral center, and since the reaction is not stereospecific, it results in a racemic mixture (equal amounts of both enantiomers).

21 Medium

21 of 45

Application +4 | -1

C{H_3} - CH - C{H_2} - C{H_3}\xrightarrow[{UV}]{{C{l_2}}}A\,\left( {\mathrm{major}} \right),\,A

View answer and explanation

Correct option: B

C{H_3} - \mathop {\mathop C\limits_{\mathop |\limits_{Cl} } }\limits^{\mathop |\limits^{C{H_3}} } - C{H_2} - C{H_3}

Option B (

C{H_3} - \mathop {\mathop C\limits_{\mathop |\limits_{Cl} } }\limits^{\mathop |\limits^{C{H_3}} } - C{H_2} - C{H_3}

) is correct because chlorination of alkanes under UV light follows a free radical mechanism, and the most stable radical is formed at the most substituted carbon.

22 Medium

22 of 45

Application +4 | -1

What mass of isobutylene is obtained from 37 g of tertiary butyl alcohol by heating with 20%

{\mathrm{H}_2}\mathrm{S}{\mathrm{O}_4}

at 363 K, if the yield is 65%?

View answer and explanation

Correct option: B

18.2 g

Option B (18.2 g) is correct because the reaction involves the dehydration of tertiary butyl alcohol to isobutylene, and the yield is calculated based on the given percentage.

23 Medium

23 of 45

Understanding +4 | -1

S{N^1}

reaction, the racemization takes place it is due to

View answer and explanation

Correct option: D

Both (1) & (2)

Option D (Both (1) & (2)) is correct because in an S\N1 reaction, the carbocation intermediate is planar and can be attacked from either side, leading to both inversion and retention of configuration, resulting in racemization.

24 Medium

24 of 45

Understanding +4 | -1

Which can be hydrolysed most easily?

View answer and explanation

Correct option: A

{\left( {{\mathrm{C}_6}{\mathrm{H}_5}} \right)_3}\mathrm{CCl}

Option A ((

\mathrm{C}_6{\mathrm{H}_5})_3\mathrm{CCl}

) is correct because the resulting carbocation is highly stabilized by resonance with three phenyl groups, making it more susceptible to hydrolysis via an S\N1 mechanism.

25 Medium

25 of 45

Application +4 | -1

20% aqueous solution of sodium chloride containing ethyl alcohol on electrolysis gives:

View answer and explanation

Correct option: D

Chloroform

Option D (Chloroform) is correct because the electrolysis of a sodium chloride solution containing ethyl alcohol can lead to the formation of chloroform through a series of reactions involving chlorination and oxidation.

26 Medium

26 of 45

Understanding +4 | -1

Best reagent for preparing a chloro alkane from an alcohol is

View answer and explanation

Correct option: A

SOC{l_2}/{C_2}{H_5}N

Option A (

SOC{l_2}/{C_2}{H_5}N

) is correct because thionyl chloride (

SOC{l_2}

) with pyridine (

{C_2}{H_5}N

) provides a clean and efficient method for converting alcohols to chloroalkanes with inversion of configuration, and the byproducts are gaseous, making purification easier.

27 Medium

27 of 45

Understanding +4 | -1

Which of the following compound shows greater reactivity towards

S{N^1}

reaction

View answer and explanation

Correct option: D

C{H_2} = CHC{H_2}Cl

Option D (

C{H_2} = CHC{H_2}Cl

) is correct because the carbocation formed after the leaving group departs is allylic and stabilized by resonance, favoring the S\N1 mechanism.

28 Medium

28 of 45

Remembering +4 | -1

Which one of the following pairs is the strongest pesticide?

View answer and explanation

Correct option: B

DDT and 666

Option B (DDT and 666) is correct because both DDT (dichlorodiphenyltrichloroethane) and 666 (benzene hexachloride) are well-known and potent pesticides.

29 Medium

29 of 45

Application +4 | -1

{C_6}{H_5}Br + Mg\xrightarrow[{}]{{{\text{dry}}\,{\text{ether}}}}A\xrightarrow[{}]{{C{O_2}}}B\xrightarrow[{}]{{{H_3}{O^ + }}}C

. IUPAC name of

C

View answer and explanation

Correct option: A

Benzene carboxylic acid

Option A (Benzene carboxylic acid) is correct because the Grignard reagent formed from bromobenzene reacts with carbon dioxide to form benzoic acid after hydrolysis.

30 Medium

30 of 45

Analyzing +4 | -1

The

\mathrm{CC}{\mathrm{l}_4}

and

\mathrm{CHC}{\mathrm{l}_3}\;

can be distinguished by the action of:

View answer and explanation

Correct option: A

R\mathrm{N}{\mathrm{H}_2} + \mathrm{KOH\;alc}.

Option A is correct because chloroform reacts with primary amines in the presence of alcoholic KOH to form isocyanides (carbylamines) which have a foul smell, while carbon tetrachloride does not react.

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