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1-Mark questions

Q.1. Give the UIUPAC name of the following compound.

Br

CH3- C = C-CH2-OH

CH3

Q2 Write the structure of the following organic compound:

2- Chloro-3- methyl pentane

Q.3 Why is chloro benzene less reactive towards nucleophilic substitution reactions?

Q4. Which of the following will undergo SN2 reaction faster and why?

Br and I

Q5.Out of C6H5-CH2-Cl & C6H5-CH(Cl)-CH3 which is more easily hydrolyzed with aq. KOH & why?

Q6. Give reason for the following observation:

p-Dichlorobenzene has higher m.p. that its o-and m- isomers.

Q7. Why is (d/l) butane-2-ol is optically inactive?

Q8. C-Cl bond length in chlorobenzene is smaller than the C-Cl bond length in halo alkane. Why?

Q9. Identify the chiral molecule in the following pair.

l Cl
Br

Q10. Complete the following equation:

Acetone
CH3-CH2-Br + NaI --------------------

Q11. Why Grignard reagent should be prepared under anhydrous conditions

2-Mark questions:
Q1. When an alkyl halide is treated with ethanolic solution of KCN, the major product is alkyl cyanide

whereas if alkyl halide is treated with ethanolic AgCN,the major product is alkyl isocyanide. Why?

Q2. Although chlorine is an electron- withdrawing group, yet it is ortho and para directing in
electrophillic aromatic substitution reactions.Why
Q3. Draw the major monohalo product in each of the following products:

SOCl2
(a) - OH -----------------

Peroxide

(b) CH2-CH =CH2 + HBr -------------------

Q4. Complete the following equations:

OH

HCl
(a) - CH2-OH -----------------

(b) CH2-CH =CH2 + HBr -------------------

Q5. Predict the reactivity in SN1

(a) C6H5CH2Br, C6H5CH (C6H5)Br, C6H5CH(CH3)Br, C6H5C(CH3)( C6H5)Br

Q6. Give reason for the following:

(a) Chloroform is stored in dark coloured bottles completely filled so that air is kept out. Also
1% ethanolic solution is added to it.
(b)Chloro ethane is immiscible with water.

Q7. Write following name reactions:

(a)Sandmayer reaction (b)Swart’ sreaction

Q8. Give reasons:

(a)Halo alkanes easily dissolve in organic solvents.

(b) Halogen compounds used in industries as solvent are alkyl chlorides and not bromides
and iodides.

Q9. How does Br2 react with CH3- C CH? How would you justify this reaction?
Q10. What are the enantiomers? Draw the possible enantiomers of 3-Methylpent-1-ene.

3-Mark questions:
Q1. How would you distinguish between following pairs of organic compounds:

(a) Cyclohexyl chloride and chlorobenzene


(b) Ethyl bromide and ethyl iodide
(c) Bromobenzene and bromo ethane

Q2. Arrange in order of boiling points.

(a) Bromobenzene, Bromoform, chloromethane,Dibromo-methane


(b) 1-chloropropane, Isopropyle chloride, 1-Chlorobutane.

Q3) How the following conversions can be carried out?

(i) Chloro ethane to n-butane

(ii)Benzene to diphenyl

(iii) But-1-ene to n-butyliodide

Q4. Write following name reactions:


(1) Wurtz’s raction (2) Gatterman reaction (3) Fittig reaction

Q5 Explain following reactions:


(1) Friedel craft’s alkylation (2) Wurtz- fittig reaction (3) Dow’s process

HOTS
HALOALKANES AND HALOARENES
Q. 1. p-Dichlorbenzene has higher melting point and lower solubility than those of
o- and m- isomers. Discuss.
Q. 2. The treatment of alkyl chlorides with aq KOH leads to the formation of alcohols
but in presence of alcoholic KOH, alkenes are the major products. Explain.
Q. 3. Explain why is Chlorobenzene difficult to hydrolyse than ethyl chloride ?
Q. 4. Tert-butyl chloride reacts with aq. NaOH by SN¹ mechanism while n-butyl chloride
reacts by SN² mechanism. Why ?

Q. 5. Allyl Chloride is more reactive than n-propyl Chloride towards nucleophilic


substitution reactions. Explain.

Q. 6. R—Cl is hydrolysed to R—OH slowly but the reaction is rapid if a catalytic


amount of KI is added to the reaction mixture.
Q. 7. Why alkyl halides are generally not prepared in laboratory by free radical
halogenation of alkanes ?
Q. 8. Why preparation of aryl iodide by electrophilic substitution requires
presence of an oxidising agent ? Why can aryl flouride not be prepared by this
method ?
Q. 9. Why aryl halides are extremely less reactive towards nucleophilic
substitution ?
Q. 10. Why does 2 bromopentane gives pent-2-ene as major product in
elimination reaction ?

WORKSHEET FOR HALOALKANES & HALOARENES


WORKSHEET NO.1

Q.1 Chloro benzene is less reactive towards nucleophilic substitution


reactions Because of --------------------------.
Q 2 SN2 reaction is given faster by -----------------
( 1-Bromobutane / 2- Bromobutane)
Q 3 SN2 reaction is given faster by -----------------
( 2-Iodobutane / 2- Bromobutane)
Q 4 Pentavalent transition state is formed in……………….. ( SN1/SN2)
Q 5 Inversion of configuration takes place in ……………….. ( SN1/SN2)
Q 6 Racemisation occurs in ………………… ( SN1/SN2)
Q 7 Bimolecular reaction takes place in …………..
(tert. Butyl bromide / 1-Bromobutane)
Q 8 Which has highest boiling points.
Bromomethane, Bromoform, Chloromethane, Dibromomethane.
Q 9 Which has lowest boiling points.
1-Chloropropane, Isopropyl chloride, 1-Chlorobutane
Q 10 Order of reactivity of SN2 reactions:
C6H5CH2Br, C6H5CH(C6H5)Br, C6H5CH(CH3)Br,
C6H5C(CH3)(C6H5)Br

WORKSHEET NO.2
Q1 Haloalkanes gives elimination reaction with ------------------
( Alc. KOH / Aquous KOH )
Q2 From haloalkanes alkenes are obtained by ………………….
( Alc. KOH / Aquous KOH )
Q3 More substituted alkene is formed as per -------------------
( Saytzeff / Markovnikoff’s rule)
Q4 dipole moment of chlorobenzene is lower than that of
cyclohexyl chloride due to ------------------
Q5 Grignard reagents should be prepared under -----------------
(anhydrous conditions / Hydrous condition)
Q6 -------------------- have higher melting point
( p-Dichlorobenzene / m-Dichlorobenzene)

Q7 Iodoform can be used as


(a) Anaesthetic (b) Antiseptic
(c) Analgesic (d) Antifebrin
Q8 The commercial uses of DDT and benzene hexachloride
are….(Hrbicides/Insecticides)
Q9 The compound added to prevent chloroform to form
phosgene gas is………. ( Ethanol/ Ethanal)
Q 10 The reaction, CH Br  Na  Product , is called…………………… ( Wurtz /
3

Finkelstein reaction)

WORKSHEET NO.3

Q1 Chloroform, when kept open, is oxidised to …………………….


Q2 For a given alkyl halide the highest density is of……………..
(RI/RCl/RBr)
Q3 Ambident nucleophile is………………. ( OH- , CN-)
Q4 CH2= CH CH3 + HBr ?
Q5 Peroxide
CH2= CH CH3 + HBr ?
Q6 On monochlorination single chloro alkane is given by
……………….. (n/Iso/Neo pentane)
Q7 CH 3 CH 2 CH 2 Br  ( A) 
KOH(alc)
(B) 
HBr
 (C ),
KOH (aq .)

Q8 Alkyl halides react with Mg in dry ether to form……………


Q9 Allyl halides gives…………. Reaction (SN1/SN2)
Q 10
Heat / Light
CH2= CH CH3 + Br2