Alkyl and Aryl Halides Reasoning

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Alkyl halides and aryl halides (reasoning)

Q(1) Explain : Peroxide effect is only observed in case of HBr and not in case
of Hf, HCl or HI.
Q(2) Darzen’s method is best method to prepare alkyl halides.
Q(3) Arrange in increasing order of boiling point :
(a) RCl, RBr, RI, RF
(b) CH3Cl, C2H5Cl, C3H7Cl, C4H9Cl
(c) Bromobutane, 2-Bromo2-methylpropane, Bromo-2-methylpropane.
Q(4) Why alkyl halides are insoluble in water?
Q(5) Arrange in increasing order of their stability: RCl, RBr, RI, RF
Q(6) Out of CH3CHCH2Cl & CH3CH2CHCl which is more reactive towards
CH3 CH3
SN1 reaction & why ?
Q(7) which would undergo SN2 reaction Faster in the following pair and why ?
(a)CH3CH2Br &

(b) CH3CH2Br & CH3CH2I


Q(8)Which would undergo SN1reaction faster in the following pair and why ?
&

Q(9)Which will react faster towards SN 2 displacement 1-Bromopentane or 2-


Bromopentane and why?
Q(10) Account for:
(a) The C-Cl bond length in chlorobenzene is shorter than that in CH 3-Cl .
(b) Chloroform is stored in dark brown bottles.
(c) (c) C6H5Cl is less reactive towards nucleophilic substitution.
(d) p-dichlorobenzene has higher M.P than ‘o’ and ‘m’ isomers.
(e) The treatment of alkyl chloride with aq KOH leads to the formation of
alcohol but in presence of Alc KOH alkene is the major product.
(f) Ethyl iodide becomes violet on standing in presence of light.
(g) Iodoform gives the ppt of AgI with silver nitrate while heating but
chloroform does not give any ppt with AgI.
(h) Aryl halides cannot be prepared by the reaction of phenol with HCl in
presence of anhy ZnCl2.
(h) A small amount of ethanol is added to chloroform bottles.
(i) haloalkanes react with Alc KCN to form alkyl cyanide as main product while
AgCN forms isocyanides as the chief product.
Q(11) Which one in the following pairs undergoes SN1 substitution reaction
faster and why ?
(a)
&

(b)
&

Q(12) Rearrange in order of reactivity towards SN2 reaction


(a) 2-Bromo2-methylbutane, 1-Bromopentane, 2-Bromopentane
(b) 1-Bromo-3-methylbutane, 2-Bromo2-methylbutane, 3-Bromo2-
methylbutane.
(c) 1-Bromobutane, 1-Bromo-2,2 –dimethylpropane, 1-Bromo-3 –
methylbutane, 1-Bromo-2 –methylbutane.
Q(13) Haloarenes are less reactive than haloalkane towards nucleophilic
substitution.
Q(14) Ethyl iodide undergoes SN2 reaction faster than ethyl chloride.
Q(15) Although chlorine is an electron withdrawing group but it is ortho and para
directing towards electrophilic substitution.
Q(16) Neopentyl chloride (CH3)3-CH2Cl does not follow SN2 reaction.
Q(17) Arrange in increasing ease towards nucleophilic substitution reaction:
(a) 4-Chloronitrobenzene, Chlorobenzene, 2,4,6 trinitrocholorobenzene,
2,4,dinitrocholorobenzene.
Q(24) which alkyl halide would you expect to react more rapidly by an SN 2
reaction:
(a) CH3CH2CH2Br & (CH3)2CHBr
(b) CH3CH2CH2CH2Cl & CH3CH2CH2CH2I.
(c) CH3)2CHCH2Cl & CH3CH2CH2CH2Cl
(d) CH3)2CHCH2CH2Cl & CH3CH2CHCH3CH2Cl
Q(25) Arrange in ease of dehydrohalogenation

(a) , C2H5Br ,

(b) Increasing bp: Propane, chloropropane,


isopropyl chloride,chlorobutane

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