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HALOALKANES & HALOARENES

Total questions: 55

Worksheet time: 55mins

Name
Class
Date
1.

1. Which alkyl halide has the highest reactivity for a particular alkyl group?

a)

R-F

b)

R-Cl

c)

R-I

d)

R-Br

2.

Write the order of increasing S1N reactivity for the following alkyl halides:

A) CH3-X

B) (CH3)2CH-X

C) (CH3)3C-X

D) (CH3)3C-CH2-X

a)

a) A>C>B>D

b)

b) C>A>B>D

c)

c) C>B>D>A

d)

d) D>C>B>A

3.

3. Which of the following is not the method of preparation of alkyl halide?

a)

a) Darzen’s method

b)

b) Halogenation of alkene

c)

c) Addition of HX on alkenes

d)

d) Hydration of alkene

4.

Toluene reacts with a halogen in the presence of iron (III) chloride giving ortho and para halo compounds. The reaction is

a)

Electrophilic elimination reaction

b)

Electrophilic substitution reaction

c)

Free radical addition reaction

d)

Nucleophilic substitution reaction

5.

Chlorobenzene is formed by reaction of chlorine with benzene in the presence of AlCl3. Which of the following species attacks the benzene ring in this reaction?

a)

Cl-

b)

Cl+

c)

AlCl3

d)

[AlCl4]-

6.

Which of the following reactions can be used to fluorinate a compound?

a)

Sandmeyer’s reaction

b)

Darzen’s reaction

c)

Hunsdicker reaction

d)

Swartz reaction

7.

If a substrate undergoing S2N reaction was of one stereoisomer, what would the product be like?

a)

.A racemic mixture

b)

One stereoisomer

c)

An unequal mixture of enantiomers

d)

A non-chiral compound

8.

. Which is the correct increasing order of boiling points of the following compounds?

a)

Bromobenzene < 1-Bromobutane < 1-Bromopropane < 1-Bromoethane

b)

Bromobenzene < 1-Bromoethane < 1-Bromopropane < 1-Bromobutane

c)

1-Bromopropane < 1-Bromobutane < 1-Bromoethane < Bromobenzene

d)

1-Bromoethane < 1-Bromopropane < 1-Bromobutane < Bromobenzene

9.

Which reagent will you use for the following reaction?

CH3CH2CH2CH3 → CH3CH2CH2CH2Cl + CH3CH2CHClCH3

a)

Cl2 /UV light

b)

NaCl + H2SO4

c)

Cl2 gas in dark

d)

Cl2 gas in the presence of iron in dark

10.

Which is 1,3-dichloro-2-methylpropane?

a)
b)
c)
d)
11.

Choose the correct IUPAC name for the compound

a)

2-chloro-2-methylpropane

b)

1-chloropropane

c)

2-chloro-2-methylbutane

d)

2-chlorobutane

12.

The geminal dihalide contains halogen bonded to

a)

Different carbon atom

b)

Same carbon atom

c)

Adjacent carbon atom

d)

All the above

13.

Complete the following reaction
R-OH + PCl5  →\rightarrow  RCl + X + HCl
X is

a)

PCl3

b)

PCl5

c)

POCl3

d)

POBr3

14.

complete the following reaction
R-OH + X  →\rightarrow  RCl + SO2 + HCl

a)

SO2

b)

SOCl3

c)

SOCl2

d)

SOCl

15.

The reaction:

R – Cl + KI → RI + KCl (in presence of acetone)Is known as

a)

Hunsdieker reaction

b)

Finkelstein reaction

c)

Ulmann reaction

d)

Wurtz reaction

16.

Haloalkanes are best obtained by

a)

Swartz reaction

b)

Darzzen's process

c)

Finkelstein process

d)

None of these

17.

Ambident nucleophile is

a)

CN

b)

H2O

c)

Cl

d)

NH2

18.

Among dihaloarenes, the melting point is highest for

a)

o-Isomer

b)

p-Isomer

c)

m-Isomer

d)

Same for all

19.

The reactivity of halides in SN2 reaction is

a)

3o>2o>1o

b)

2o>1o>3o

c)

1o>3o>2o

d)

1o>2o>3o

20.

Haloalkane is a polar molecule that undergoes nucleophilic substitution through SN1 and SN2. Arrange the following haloalkanes in order of increasing rate of unimolecular nucleophilic substitution reaction:

I. 2-chloro-2-methylpropane

II. 2-chlorobutane

III. 1-chlorobutane

a)

I< II < III

b)

I< III < II

c)

III< I < II

d)

III< II < I

21.

Which of the following is a chiral molecule?

a)

CH2BrI

b)

CH3CBr2Cl

c)

(CH3)2CHCl

d)

CH3CHBrCH2CH3

22.

The position of –Br in the compound in CH3CH=CHC(Br)(CH3)2 can be classified as ____________.

a)

Allyl

b)

Aryl

c)

Vinyl

d)

Secondary

23.

Alkaline hydrolysis of (CH3)3CBr involves two steps as follows.

(CH3)3CBr → (CH3)3C+ + Br- slow

(CH3)3C+ + OH- → (CH3)3COH fast

Which of the following shows the rate equation for the reaction scheme?

a)

Rate = k[OH-]

b)

Rate = k[(CH3)3CBr]

c)

Rate = k[(CH3)3CBr]2

d)

Rate = k[(CH3)3CBr][OH-]

24.

Assertion: Halogen acids react with alcohols to form haloalkanes.

Reason: Order of reactivity of halogen acids HCl>HBr>HI

a)

Both assertion and reason are true and the reason is the correct explanation of the assertion.

b)

Both assertion and reason are true but reason is not the correct explanation of the assertion.

c)

Assertion is true but reason is false.

d)

Assertion is false but reason is true.

25.

Assertion: Electron withdrawing groups in aryl halides increases the reactivity towards nucleophilic substitution.

Reason: 2, 4-Dinitrochlorobenzene is more reactive than chlorobenzene.

a)

Both assertion and reason are true and the reason is the correct explanation of the assertion.

b)

Both assertion and reason are true but reason is not the correct explanation of the assertion

c)

Assertion is true but reason is false

d)

Assertion is false but reason is true.

26.

Assertion (A): Phosphorus chlorides (tri and penta) are preferred over thionyl chloride for the preparation of alkyl chlorides from alcohols.

Reason (R): Phosphorus chlorides give pure alkyl halides.

a)

Assertion and Reason both are correct and Reason is the correct explanation of Assertion.

b)

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

c)

Assertion is correct but Reason is wrong.

d)

Assertion and Reason both are wrong statements

27.

In SN1 the order of reactivity of halide is:

a)

30 > 20 > 10 > methyl

b)

Methyl > 10>20 > 30

c)

30 > 20 > methyl > 10

d)

20 > 10 > methyl > 30

28.

In SN1 type of mechanism the intermediate species is:

a)

A free radical

b)

A carbonium ion(carbo cation)

c)

A carboanion

d)

None of these

29.

Ethyl bromide on treatment with silver cyanide give :

a)

Ethyl acetate

b)

Ethyl iso cyanide

c)

Ethyl cyanide

d)

Ethyl amine

30.

SN2 reaction involves the formation of __________ intermediate

a)

Carbocation

b)

Carboanion

c)

Transition state

d)

None of these

31.

Ethylmagnesium chloride is an example of Grignard reagent. It may be used to prepare

a)

ethene

b)

ethanol

c)

1-propanol

d)

ethanoic acid

32.

Which is the correct increasing order of boiling points of the following compounds? 1-Iodobutane, 1-Bromobutane, 1-Chlorobutane, Butane

a)

Butane < 1-Chlorobutane < 1-Bromobutane < 1-Iodobutane

b)

1-Iodobutane < 1-Bromobutane < 1-Chlorobutane < Butane

c)

Butane < 1-Iodobutane < 1-Bromobutane < 1-Chlorobutane

d)

Butane < 1-Chlorobutane < 1-Iodobutane < 1-Bromobutane

33.

Halogen compounds have--------- boiling point than the parent hydrocarbons

a)

Higher

b)

Lower

c)

Same

d)

Unpredictable

34.

Give the reaction conditions for dow's processes

a)

NaOH , 623K , 300atm in Basic medium

b)

NaOH , 443K , 300atm in acidic medium

c)

NaOH , 623K , 300atm in acidic medium

d)

NaOH , 368K , 300atm in Basic medium

35.

what is a racemic mixture ?

a)

mixture of 2 dextro enantiomers

b)

mixture of dextro & laevo enantiomers

c)

mixture of chiral molecules

d)

mixture of 2 laevo enantiomers

36.

why aryl halides are not much prone to nucleophilic substitution reaction ?

a)

C-Cl bond length is more ( 177 pm ) in aryl halides

b)

C-Cl bond is stable due to resonance

c)

C-Cl bond acquires a partial double bond character due to resonance of pi electrons

d)

C-Cl bond is more polarised

37.

what are the reaction conditions for wurtz - fittig reaction?

a)

Na + dry ether

b)

Na + aq.NaOH

c)

Na in acidic medium

d)

Na in conc.HCl

38.

why chloroform is stored in closed dark coloured bottles ??

a)

Chloroform is very poisonous

b)

Chloroform causes damage to CNS , liver , kidneys

c)

Chloroform is a very reactive gas

d)

Chloroform is oxidised by air to phosgene

39.

The compound ethylisocyanide is prepared by the reaction between:

a)

C2H5Br and KCN

b)

C2H5Br and AgCN

c)

C2H5Br and HCN

d)

C2H5Br and ammonia

40.

Which of the following alkyl halide is most readily undergoes hydrolysis by SN1 mechanism?

a)

CH3CH2CH2Cl

b)

CH3Cl

c)

(CH3)2 CHCl

d)

(CH3)3 CCl

41.

complete the following reaction

R-X + KNO2 → A + KX

A is

a)

RNO2

b)

RONO

c)

RNO

d)

RNO3

42.

What is the type of hybridization of each carbon in CH3CN ?

a)

Sp3,sp2

b)

Sp2, sp

c)

Sp3, sp

d)

sp3, sp2

43.

Assertion : The boiling points of alkyl halides decrease in the order : RI > RBr > RCl > RF

Reason : The boiling points of alkyl chlorides, bromides and iodides are considerably higher than that of the hydrocarbon of comparable molecular mass

a)

(i) Assertion and reason both are correct and reason is correct explanation of assertion.

b)

(ii) Assertion and reason both are wrong statements

c)

(iii) Assertion is correct but reason is wrong statement

d)

(iv) Assertion is wrong but reason is correct statement.

e)

(v) Assertion and reason both are correct statements but reason is not correct explanation of assertion.

44.

Why does the reaction

C2H5X + OH- → C2H5OH + X-

occur faster if X is iodine instead of Bromine?

a)

the I- ion is a stronger nucleophile than the Br- ion.

b)

the I- ion is less hydrated in water than the Br- ion

c)

C-Br bond is more polar than the C-I bond

d)

the C-Br bond is stronger than the C-I bond

45.

Alkyl halide on treatment with aqueous KOH give

a)

Acids

b)

Alcohols

c)

Aldehydes

d)

Alkanes

46.
test for 1-chlorobutane and 1-iodobutane
a)
use silver nitrate, AgNO3 -> AgCl (white precipitate). -> AgI (yellow ppt).
b)
use silver nitrate, AgNO3 -> AgCl (yellow ppt). -> AgI (white precipitate).
47.

State the type of reaction that takes place when compound V reacts with an aqueous solution of sodium hydroxide.

a)

base catalytic elimination

b)

electrophilic addition

c)

electrophilic substitution

d)

nucleophilic substitution

48.

If no bond around the stereocenter is broken the product is said to have

a)

Inversion of configuration

b)

retention of configuration

49.

The rate of reaction for SN2 reactions is

a)

Rate = k [RX] [Nucleophile]

b)

Rate= k[RX]

50.

Nitriles can be formed by reacting haloalkanes with......

a)

Amines

b)

Amides

c)

Sodium Cyanide or Potassium Cyanide

d)

Potassium Nitrile

51.

What is the organic product when 2-chlorobutane reacts with aqueous sodium hydroxide?

a)

Butene

b)

Butane

c)

Butan-2-ol

d)

Sodium butanoate

52.

When 1-chloropropane reacts with a hot ethanolic solution of sodium hydroxide, the type of reaction is....

a)

Nucleophilic substitution

b)

Nucleophilic addition

c)

Electrophilic addition

d)

Elimination

53.

Which is the correct IUPAC name for CH3-CH(C2H5) -CH2-Br?

a)

1-Bromo-2-ethylpropane

b)

1-Bromo-2-ethyl-2-methylethane

c)

1-Bromo-2-methylbutane

d)

2-Methyl-1-bromobutane

54.

What is ‘A’ in the reaction?

a)
b)
c)
d)
55.

Which of the following alkyl halides will undergo SN1 reaction most readily?

a)

(CH3)3C—F

b)

(CH3)3C—Cl

c)

(CH3)3C—Br

d)

(CH3)3C—I

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