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WorksheetsHALOALKANES AND HALOARENES
Total questions: 100
Worksheet time: 50mins
Which of the following is a primary halide?
iso-propyl iodide
sec-butyl iodide
tert-butyl bromide
neo-hexyl chloride
Classify the following compounds as primary, secondary and tertiary halides.
i) 1-Bromobut-2-ene
ii) 4-Bromopent-2-ene
iii) 2-Bromo-2-methylpropane
(i) secondary, (ii) tertiary, (iii) primary
(i)primary, (ii) secondary, (iii) tertiary
(i) secondary, (ii) primary, (iii) tertiary
(i)primary, (ii) tertiary, (iii) secondary
Which of the following is not an allyclic halide?
1-Bromobut-2-ene
4-Bromopent-2-ene
4-Bromobut-1-ene
3-Bromo-2-methylbut-1-ene
Haloalkanes contains halogen atom(s) attached to the sp3 hybridised carbon atom of an alkyl group. Identify haloalkane from the following compounds.
(i) 2-Bromopentane
(ii) Vinyl chloride
(iii) 2-Chloroacetophenone
(iv) Trichloromethane
only (i) and (iv)
only (ii) and (iv)
(ii) only
only (i),(ii) and (iii)
Match the column I with II mark the appropriate choice.
(A)(i), (B)(ii), (C) (iv), (D)(iii)
(A)(iv), (B)(i), (C) (iii), (D)(ii)
(A)(iii), (B)(iv), (C) (ii), (D)(i)
(A)(ii), (B)(iii), (C) (i), (D)(iv)
The IUPAC name of tertiary butyl chloride is
4-chlorobutane
1,2-chloro-3-methylpropane
2-chloro-2-methylpropane
3-chlorobutane
The IUPAC name of (CH3)2CH-CH2-CH2Br is
1-bromopentane
2-methyl-4-bromobutane
1-bromo-3-methylbutane
2-methyl-3-bromopropane
Which of the following halides is not correct according to the name and classification
CH3C(Cl)(C2H5)CH2CH3 2-chloro-2-ethylbutane, secondary haloalkane
(CH3)2CHCH(Cl)CH3 2-chloro-3-methylbutane, secondary haloalkane
CH3CH2C(CH3)2CH2I 1-iodo-2,2-dimethylbutane, primary haloalkane
Which of the following is not correctly matched with its IUPAC name?
CHF2CBrClF: 1-bromo-1-chloro-1,2,2-trifluoroethane
o-BrC6H4CH(CH)3CH2CH3: 2-Bromo-1-methylpropylbenzane
(CCl3)3CCl: 2-(Trichloromethyl)-1,1,1,2,3,3,3-heptachloropropane
CH3C(p-ClC6H4)2CH(Br)CH3: 2-Bromo-3,3-bis(4-chlorophenyl)butane
The main difference in C-X bond of a haloalkane and a haloarene is
C-X bond in haloarenes acquires a double bond character due to higher electronegativity of X than haloalkanes.
C-X bond in haloalkanes is shorter than haloarenes.
In haloalkanes the C attached to halogen in C-X bond is sp3 hybridised while in haloarenes it is sp2 hybridised.
haloalkanes are less reactive than haloarenes due to difficulty in C-X cleavage in haloalkanes
Which of the following compounds can yield only one monochlorinated product upon free radical chlorination?
2,2-dimethylpropane
2-methylpropane
2-methylbutane
n-butane
Bromination of methane in presence of sunlight is a
nucleophilic substitution
free radical substitution
electrophilic substitution
nucleophilic addition
nucleophilic addition
electrophilic addition
free radical addition
electrophilic substitution
The negative part of the addendum ( the molecule to be added) adds on to the carbon atom of the double bond containing the least number of hydrogen atoms. This rule is known as
Saytzeff’s rule
Hoffmann rule
Peroxide rule
Markovnikov’s rule
Methyl bromide reacts with AgF to give methyl fluoride and silver bromide. This reaction is called
Swarts reaction
Wurtz reaction
Fiitig reaction
Finkelstein reaction
Which of the following molecules has higher dipole moment?
CH2Cl2
CCl4
CH3Cl
CHCl3
Which of the following compounds has the highest boiling point?
CH3CH2CH2Cl
CH3CH2CH2CH2Cl
(CH3)3CCl
CH3CH(CH3)CH2Cl
Which one of the following is not correct order of boiling point of the alkyl/aryl halides?
CH3(CH2)CH3Cl > CH3(CH2)2Cl
CH3(CH2)3Cl>CH3CH2CHClCH3
CHCl3> CH2Cl2
(CH3)3CCl>(CH3)2CHCH2Cl
Arrange the following compounds in decreasing order of their boiling points.
i) CH3Br
ii) CH3CH2Br
iii) CH2CH2CH2Br
iv) CH3CH2CH2CH2Br
(i)>(iii)>(ii)>(iv)
(i)>(ii)>(iii)>(iv)
(iii)>(iv)>(i)>(ii)
(iv)>(iii)>(ii)>(i)
Which of the following compounds will have highest melting point?
m-dicholorbenzene
chlorobenzene
p-dichlorobenzene
o-dichlorobenzene
Alkyl halides are immiscible in water though they are polar because
C-X bond cannot be broken easily
they react with water to give alcohols
they are stable compounds are not reactive
they cannot form hydrogen bonds with water
Cyanide ion acts as an ambident nucleophile. From which end its acts as a stronger nucleophile in aqueous medium?
it has same strength from both the ends
it acts as a stronger nucleophile from carbon end
it depends on the nature of the alkyl halide
it acts as a stronger nucleophile from nitrogen end
Identify the products (A) and (B) in the reactions
(A)-RCN,(B)-RCN
(A)-RNC, (B)-RCN
(A)-RNC, (B)-RNC
(A)-RCN, (B)-RN
Butanate nitrile can be prepared by heating
butyl alcohol with KCN
propyl alcohol with KCN
propyl chloride with KCN
butyl chloride with KCN
Ethyl alcohol is obtained with ethyl chloride is boiled with
aqueous KOH
water
aqueous KMnO4
alcoholic KOH
Which of the following alkyl halides undergoes hydrolysis with aqueous KOH at the fastest rate?
CH3CH2CH(Br)CH3
CH3CH2CH2CH2Cl
CH3CH2CH2Cl
CH3CH2Cl
Identify the product of the following reaction. ClCH2CH2Br+KCN product
CNCH2CH2CH2CN
ClCH2CH2CH2CN
CNCH2CH2Br
The alkyl halide is converted into an alcohol by
addition
elimination
substitution
dehydrohalogenation
An alkyl halide RX reacts with KCN to give propane nitrile RX is
C3H7Br
C5H11Br
C4H9Br
C2H5Br
In SN2 reaction the sequence of bond breaking and bond formation is as follows
bond breaking and formation take place randomly
bond formation is followed by breaking
bond breaking followed by formation
bond breaking and formation occur simultaneously
Which of the following statements is not correct about SN2 reaction of alkyl halides?
The rate of reaction depends upon the concentration of nucleophile
The bond formation and bond breaking take place in one step
SN2 mechanism is predominant in tertiary alkyl halides
Nucleophile attacks the carbon from the side opposite to where the leaving group is attached
Tertiary alkyl halides are practically inert to substitution by 2 mechanism because
there is inductive effect
there is steric hindrance
the rate of reaction is faster in SN2 mechanism
the carbocation formed is unstable
Which of the following statements regarding the SN1 reaction shown by alkyl halide is not correct?
the SN1 reaction involves the inversion of configuration of the optically active subtract
the SN1 reaction on the chiral starting material ends up with racemization of the product
the more stable the carbocation intermediate the faster the SN1 reaction
the added nucleophile plays no kinetic role in SN1 reaction
Which of the following haloalkanes is most reactive?
1-chloropropane
2-chloropropane
2-bromopropane
1-bromopropane
Which of the following is the most reactive towards nucleophilic substitution reaction?
CH3CH=CH-Cl
CH2=CH-Cl
ClCH2-CH=CH2
C6H5Cl
Which of the following alkyl halides is hydrolysed by SN1 mechanism?
CH3CH2Cl
CH3Cl
CH3CH2CH2Cl
(CH3)3CCl
Which of the following is most reactive towards aqueous NaOH?
C6H5CH2Cl
BrC6H4Br
C6H5Cl
C6H5Br
Which of the following haloalkanes reacts with aqueous KOH most easily?
2-bromo-2-methylpropane
2-chlorobutane
1-bromobutane
2-bromobutane
Which alkyl halide exhibits complete racemization in SN1 reaction?
C6H5CH2Cl
(CH3)2CHCl
CH3CH2Cl
CH3CH2CH2Cl
The order of reactivity of various alkyl halides towards nucleopilic substitution follows the order
R-Cl>R-Br>R-I>R-F
R-I>R-Br>R-Cl>R-F
R-Br>R-I>R-Cl>R-F
R-F>R-Cl>R-Br>R-I
Alkyl halides are formed when thionyl chloride and _____ are refluxed in presence of pyridine.
The order of reactivity (30>20>10) is due to +1 effect of the alkyl group which ____ the polarity of C-X bond.
aldehydes, changes
acids, decreases
ketones, decreases
alcohols, increases
2-Bromo-3,3-dimethylbutane on reaction with aqueous KOH yields X as the major product. X is
2,3-dimethylbutan-2-ol
2,3,3-trimethylpropan-1-ol
2,2-dimethylpropan-2-ol
2,2-dimethybutan-3-ol
Among the isomers of C6H11Cl, the one which is chiral is
i) 2,2-dimethyl-1-chloropropane
ii) 2-chloropentane
iii) 2-methyl-2-chlorobutane
iv) 3-chloopentane
(i) ,(ii) and (iii) only
(i) and (iii) only
(ii) only
(i) and (ii) only
Ethylene dichloride and ethylidene chloride are isomeric compounds. The false statement about these isomers is that they
contain the same percentage of chlorine
are position isomers
react with alcoholic potash and give the same product
are both hydrolysed to the same product
A mixture of 1-chloropropane and 2-chloropropane when treated with alcoholic KOH gives
a mixture of prop-1-ene and prop-2-ene
prop-1-ene
propanol
prop-2-ene
An alkyl halide with molecular formula, C6H5Br on dehydrohalogenation gives two isomeric alkenes X and Y with molecular formula, C6H12. On reductive ozonolysis X and Y gave four compounds CH3COCH3, CH3CHO, CH3CH2CHO and (CH3)2CHCHO. The alkyl halide is
3-bromo-2-methylpentane
2,2-dimethyl-1-bromobutane
4-bromo-2-methylpentane
2-bomo-2,3-dimethylbutane
Arrange the following alkyl halides in order of dehydrohalogenation C2H5I, C2H2Cl, C2H5Br, C2H5F
C2H5I> C2H2Cl> C2H5Br> C2H5F
C2H5F> C2H2I> C2H5Br> C2H5Cl
C2H5F> C2H2Cl> C2H5Br> C2H5I
C2H5I> C2H2Br> C2H5Cl> C2H5F
2-Chloro-2-methylpropane on reaction with alc.KOH gives X as the product. X is
2-methyobutan-2-ol
but-2-ene
2-methylbut-1-ene
2-methylprop-1-ene
An alkyl chloride produces a single alkene on reaction with sodium ethoxide and ethanol. The alkene further undergoes hydrogenation to yield 2-methylbutane. Identify the alkyl chloride amongst the following compounds.
ClCH2CH(CH3)CH2CH3
CH3C(Cl)(CH3)CH2CH3
ClCH2CH(CH3)CH2CH3
ClCH2CH2CH2CH3
Reaction of trans-2-phenyl-1-bromocyclopentane on reaction with alcoholic KOH produces
1-phenylcyclopentene
4-phenylcyclopentene
3-phenylcyclopentene
2-phenylcyclopentene
Elimination of bromine from 2-bromobutane result in the formation of
predominantly 2-butene
predominantly 2-butyne
equimolar mixture of 1 and 2-butene
predominantly 1-butene
In the given reaction what will be the final product?
CH3CHICH2I
CH3CH2CHI2
CH3CH2 CH2I
CH3CH2CH2CH2CH3
Grignard reagent, a very useful starting compound for a number of organic reactions can be prepared by
reaction of MgCl2 with ether and alcohol
reaction of alkyl halides with a solution of magnesium hydroxide
reaction of alkyl halide with magnesium in presence of alcohol
reaction of alkyl halides with dry magnesium powder in the presence of dry ether
The order of reactivities of methyl halides in the formation of Grignard reagent is
CH3Cl>CH3Br>CH3I
CH3Br>CH3I>CH3Cl
CH3I>CH3Br>CH3Cl
CH3Br>CH3Cl>CH3I
Alkyl halides react with metallic sodium in dry ether producing
alkanes with double the no. of carbon atoms
alkenes with same no. of carbon atoms
alkanes with same no. of carbon atoms
alkenes with triple the no. of carbon atoms
On treating a mixture of two alkyl halides with sodium metal in dry ether, 2-methylpropane was obtained. The alkyl halides are
chloromethane and chloroethane
2-chloropropane and chloromethane
chloromethane and 1-chloropropane
2-chloropropane and chloroethane
Chlorobenzene on treatment with Na in dry ether gives diphenyl. The name of the reaction is
Wurtz-Fittig reaction
Gattermann reaction
Fittig reaction
Sandmeyer reaction
Tertiary butyl bromide on reaction with Na methoxide mainly gives
propene
tert-butyl ethyl ether
iso-propyl alcohol
2-methylpropene
Aryl halides are less reactive towards nucleophilic substitution reactions as compared to alkyl halides due to
resonance stabilization in aryl halides
inductive effect in aryl halides
formation of a less stable carbonium ion in aryl halides
presence of double bonds in alkyl halides
Chloroform is kept in dark coloured bottles because
it reacts with clear glass
it is oxidized to poisonous gas, phosgene in sunlight
it undergoes chlorination in transparent glass bottles
it starts burning when exposed to sunlight
Triiodomethane has antiseptic property because of
formation of phosgene gas
liberation of iodoform
liberation of free iodine
none of these
The fire extinguisher ‘pyrene’ contains
chloroform
carbon di oxide
carbon tetrachloride
carbon disulphide
An organic halogen compound which is used as refrigerant in refrigerators and ac is
BHC
CHCl3
CCl4
freon
Which one is correct?
freons are chlorofluorocarbons
freons are used as refrigerants
Freon-14 is CF4, freon-13 is CF3Cl, Freon-12 is CF2Cl2 and freon-11 is CFCl3
all the above
Match the column I with II and mark the appropriate choice.
(A)(iv), (B)(iii), (C) (ii), (D)(i)
(A)(iii), (B)(i), (C) (iv), (D)(ii)
(A)(i), (B)(ii), (C) (iii), (D)(iv)
(A)(ii), (B)(iii), (C) (i), (D)(iv)
Which of the following is not correctly matched?
Halogen acid react with alcohols to form alkyl halides. The reaction follows a nucleophilic substitution mechanism. What will be the major product of the following reaction?
CH3CH2CH2CH2CH2Cl
Match the column I with II and mark the appropriate choice.
(A)(iii), (B)(iv), (C) (i), (D)(ii)
(A)(iv), (B)(iii), (C) (i), (D)(ii)
(A)(iii), (B)(iv), (C) (ii), (D) (i)
(A)(iv), (B)(iii), (C) (ii), (D)(i)
Which of the following statements is correct?
in the reaction of toluene with Cl2/FeCl2, ortho and para isomers are easily separated
similar reaction with iodine is reversible nature
in the electrophilic substitution of toluene with Br2, iron(III) bromide acts as Lewis acid.
all of these
The IUPAC name of the compound
1-fluoro-4-methyl-2-nitrobenzene
4-methyl-1-fluoro-2-nitrobenzene
4-fluoro-1-methyl-3-nitrobenzene
2-fluoro-5-methyl-1-nitrobenzene
Match the isomers given in column I with their names given in column II and mark the appropriate choice
(A)(iii), (B)(i), (C) (iv), (D)(ii)
(A)(iv), (B)(iii), (C) (ii), (D)(i)
(A)(ii), (B)(iii), (C) (iv), (D)(i)
(A)(i), (B)(ii), (C) (iii), (D)(iv)
Which of the following reactions follows Markovnikov’s rule?
C3H6+Br2
C2H4+HBr
C3H6+Cl2
C3H6+HBr
A compound X with molecular formula C7H8 is treated with Cl2 in presence of FeCl3. Which of the following compounds are formed during the reaction?
Among the choice alkyl bromide, the least reactive bromide in SN2 reaction
1-bromo-3-methylbutane
1-bromopentane
1-bromo-2-methylbutane
2-bromo-2-methylbutane
Toulene reacts with a halogen in the presence of iron(III) chloride giving ortho and para halo compounds. The reaction is
electrophilic elimination reaction
free radical addition reaction
electrophilic substitution reaction
nucleophilic substitution reaction
Which of the following is an example of vic-dihalide?
1,2-Dichloroethane
Dichloromethane
Ethylidene chloride
Allyl chloride
The position of -Br in the compound CH3CH=CH(Br)(CH3)2 can be classified as _______.
allyl
aryl
vinyl
secondary
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?
Cl-
Cl+
AlCl3
[AlC4]-
Ethylidene chloride is a/an _______.
vic-dihalide
gem-dihalide
allylic halide
vinylic halide
A primary alkyl halide would prefer to undergo ________.
SN1 reaction
SN2 reaction
σ-elimination
racemisation
Which of the following alkyl halides will undergoes SN1 reaction most readily?
(CH3)3C-F
(CH3)3C-Cl
(CH3)3C-Br
(CH3)3C-I
Which is the correct IUPAC name for
1-bromo-2-ethylpropane
1-bromo-2-ethyl-2-methylethane
1-bromo-2-methylbutane
2-methyl-1-bromobutane
What should be the correct IUPAC name for diethylbromomethane?
1-bromo-1,1-diethylmethane
3-bromopentane
1-bromo-1-ethylpropane
1-bromopentane
Molecules whose mirror image is non-superimposable over them are known as chiral. Which of the following molecules is chiral in nature?
2-bromobutane
1-bromobutane
2-bromopropane
2-bromopropan-2-ol
Reaction of C6H5CH2Br with aqueous solution hydroxide follows________.
SN1 mechanism
SN2 mechanism
any of the two above depending upon the temperature of reaction
satyzeff rule
Which is the correct increasing order of boiling points of the following compounds?
1-iodobutane,1-bromobutane,1-chlorobutane,butane
Butane<1-chlorobutane<1-bromobutane<1-iodobutane
1-iodobutane<1-bromobutane<1-chlorobutane<butane
Butane < 1-iodobutane<1-bromobutane<1-chlorobutane
Butane<1-chlorobutane<1-iodobutane<1-bromobutane
Consider the following sN2 reactions
I. RX+Y- R-Y+X-
II. RX+Y R-Y++X-
III. RX++Y- R-Y+X
IV. RX++Y R-Y++X
In which reactions there is large increase and large decrease n rate if reaction respectively with increase in polarity of the solvent?
II &III
II&IV
I&IV
IV&I
In two separate experiments equal quantities of an alkyl halide C4H9Cl, were treated at the same temperature with equal volume of 0.1 molar and 0.2 molar solution of NaOH respectively. In both the experiments t1/2 of the two reactio were the same. The most likely structure of halide is
CH3CH2CH2CH2Cl
CH3CH(Cl)CH2CH3
(CH3)2CHCH2Cl
(CH3)3CCl
36.4g oF 1,1,2,2-tetrachloropropane was heated with Zn dust and the product was bubbled through ammoniacal AgNO3. What is the weight of precipitate obtained?
30.0g
29.4g
28.0g
25.7g
In the given sequence of reaction, what would be the structure of (A)?
PhCOCH3
PhCH(OH)CH3
PhCOONa
PhC(Cl2)CH3
Match the reaction given in column I with the type of reaction mentioned in column II and mark the appropriate choice.
(A) (iv), (B) (i), (C) (ii), (D) (iii)
(A) (ii), (B) (iii), (C) (iv), (D) (i)
(A) (i), (B) (ii), (C) (iv), (D) (iii)
(A) (iii), (B) (i), (C) (ii), (D) (iv)
Which of the following products as shown by the dehydrohalogenation of alkyl halides with sodium ethoxide in ethanol is correctly marked as major product?
only (i) and (ii)
only (i) and (iii)
only (ii) and (iii)
only (ii)
In the following pairs of halogen compounds, which compound undergoes faster SN 1 reaction?
An unkown alkyl halilde (A) reacts with alcoholic KOH to produce a hydrocarbon (C4H8) as the major product. Ozonolysis of the hydrocarbon affords one mole of propanaldehyde and one mole of fomaldehyde. Suggest with organic compound among the following is the correct structure of the above alkyl halide(A)?
CH3CHBrCH2CH3
CH3CH(Br)CH(Br)CH3
CH3CH2CH2CH2Br
Br(CH2)4Br
0.0852g of an organic halide (A) when dissolved in 2.0g of camphor, the melting point of the mixture was found to be 167 . Compound(A) when heated with Na gives a gas (B). 280ml of gas (B) at STP weighs 0.375g. What would be A in the whole process ? (Kf for camphor =40,m.pt of camphor=179 ).
C2H5Br
CH3I
(CH3)2CHI
C3H7Br
10g mixture of iso-butane & iso-butene requires 20g of Br2 (in CCl4) for complete addition. If 10g of the mixture is catalytically hydrogenated & the entire alkane is monobrominated in the presence of light at 127 , how much of it would be formed?
(atomic weight of Br=80)
24.21g
20.0g
30.0g
12g
Bottles containing C6H5I & C6H5 CH2I lost their original labels. They were labelled A &B for testing . A&B were separately taken in test tubes and boiled with NaOH solution. The end solution in each tube was made acidic with dil.AgNO3
Solution added. Solution B gave a yellow precipitate. Which one of the following is true for the experiment?
addition of HNO3 is unnecessary
A was C6H5I
A was C6H5 CH2I
A&B cant be predicted by this experiment
Cyclobutyl bromide on treatment with Mg in dry ether forms an organometallic compound (A). the organometallic compound reacts with ethanal to give an alcohol(B) after mild acidification. Prolonged treatment of OH (B) with an equivalent amount of HBr gives (C). What will be the product ‘C?
1-chloro-1-ethylcyclopentane
1-bromo-1-methylcyclopentane
3-bromo-2-methylcyclopentane
none of these
Arrange the following compounds in the increasing order of their densities.
(I)<(II)<(III)<(IV)
(I)<(III)<(IV)<(II)
(IV)<(III)<(II)<(I)
(II)<(IV)<(III)<(I)
Cholormethane on treatment with excess of ammonia yields mainly
N-methylmethanamine (CH3-NH-CH3)
methanamine (CH3NH2)
mixture containing all these in equal proportion
