BLS INTERNATIONAL SCHOOL, HATHRAS

(Affiliated to CBSE, New Delhi, Affiliation No.-2131917, School Code-60805)

QUESTION BANK- 2024-25
Subject: Chemistry (043)
Class – XII Topic: Haloalkanes and Haloarenes
----------------------------------------------------------------------------------------------------------------------------- -----
Section – A (2 Marks each)

Q1. Complete the following reactions :

Q2. What happens when :

(i) Propene is treated with HBr in presence of peroxide.
(ii) Benzene is treated with methyl chloride in presence of AlCl3

Q3. (i) Although chlorine is an electron withdrawing group, yet it is o, p-directing in electrophilic aromatic
substitution reactions. Explain, why is it so?
(ii) Why is sulphuric acid not used during the reaction of alcohols with KI?

Q4. Complete the reactions :

Q5. Identify the products :

Q6. An organic compound A reacts with PCl5 to give compound B. Compound B reacts with Na/ether to give n-
butane. What are compounds A and B ?

Q7. Name the reagents used to convert :

(i) 2-chloropropane to 2-nitropropane (ii) Chloroethane to n-butane

Q8. Write short note on : (i) Sandmeyer reaction (ii) Finkelstein reaction

Section – B (3 Marks each)

Q9. Answer the following :

(i) Haloalkanes easily dissolve in organic solvents, why ?
(ii) What is known as racemic mixture ? Give example.
(iii) Of the two bromo derivatives, C6 H5 CH(CH3 )Br and C6 H5 CH(C6 H5 )Br, which one is more reactive in SN 1
substitution reaction and why ?

Q10. How the following conversions can be carried out ?

(i) But-1-ene to n-butyl iodide
(ii) Tert-butyl bromide to isobutyl bromide
(iii) Ethanol to but-1-yne.

Q11. An organic compound ‘A’ having molecular formula C 4 H8 on treatment with dil. H2 SO4 give another compound
‘B’. B on treatment with conc. HCl and anhyd. ZnCl 2 gives ‘C’. C on treatment with sodium ethoxide gives back
‘A’. Identify the compound. Write the equations involved.
Q12. Account for the following :
(i) A small amount of ethyl alcohol is added to CHCl3 stored for use as an anaesthetic.
(ii) The Chloroform is often filled in dark coloured bottles.
(iii) The use of DDT as an insecticide is banned by Indian Government.

Q13. (i) What are ambident nucleophiles ? Explain with an example.

(ii) Convert ethyl bromide to diethyl ether.
(iii) What are freons ?

Q14. (i) Which isomer of C4 H9 Cl will have the lowest boiling point ?
(ii) Predict the alkenes that would be formed by dehydrohalogenation with sodium ethoxide and ethanol.
Predict major alkenes : (a) 2-chloro-2-methylbutane (b) 3-bromo-2, 2, 3-trimethylpentane

Q15. Write the main products when :

(i) n-butyl chloride is treated with alcoholic KOH
(ii) 2, 4, 6-trinitrochlorobenzene is subjected to hydrolysis.
(iii) Methyl chloride is treated with AgCN

Q16. Write the major product in each of the following reaction:

Section – C (5 Marks each)

Q17. How would you bring about the following conversions :

(i) Propene to 2-bromopropane (ii) Bromoethane to propanoic acid
(iii) 1-chloropropane to 1-propanol (iv) Ethanol to chloroethane
(v) 1-iodopropane to propene

Q18. What happens when : (Give chemical reactions)

(i) Cyclohexanol is treated with thionyl chloride
(ii) p-hydroxybenzyl alcohol is heated with HCl.
(iii) Ethyl bromide is refluxed with NaI in acetone.
(iv) Ethyl bromide is treated with mercurous fluoride
(v) Chlorobenzene is subjected to hydrolysis.

Q19. Account for the following :

(i) Haloalkenes undergo nucleophillic substitution whereas haloarenes undergo electophillic substitution
(ii) p-methoxybenzyl bromide reacts faster than p-nitrobenzyl bromide with sodium ethoxide to form an
ether product.
(iii) Organic halogen compounds used as solvents in industry are chlorides rather than bromides and iodides.
(iv) When an alkyl halide is treated with ethanolic solution of KCN, the major product is alkyl cyanide where
as if alkyl halide is treated with AgCN, the major product is alkyl isocyanide.
(v) Alkyl halides are insoluble in water though they contain a polar C – X bond.
(vi) SN1 reactions are accompanied by racemization in optically active alkyl halides
 Section – D (4 Marks case based question)

Read the following paragraph and answer the following questions:

Q20. Polarity of carbon halogen bond is responsible for the SN reactions of alkyl halides which mostly occur by SN 1
and SN2 mechanism. The rates of SN2 reactions among other things are governed by steric factors while that of
SN1 reactions are governed by the stability of the intermediate carbocations. Chirality has a profound rule in
understanding the mechanism of SN1 and SN2 reactions. Whereas the SN2 reactions of chiral alkyl halides are
accompanied by inversion of configuration and that of SN1 reactions are characterised by racemization.
(i) An SN2 reaction at an asymmetric carbon of a compound always give:
(a) An enantiomer of the substrate (b) a product with opposite optical rotation
(c) A mixture of diastereomers (d) a single stereoisomer

(ii) SN reaction will be fastest in case of:

(a) 1-Chloro-2,2-dimethyl propane (b) 1-Iodo-2,2-dimethyl propane
(c) 1-Bromo-2,2-dimethyl propane (d) 1-Flouro-2,2-dimethyl propane

(iii) SN1 reaction will be favoured in which of the following solvents:

(a) Benzene (b) carbon tetrachloride
(c) Acetic acid (d) Carbon disulphide

(iv) In the hydrolysis of 3-methyl-3-bromohexane, which if the following statement is not correct?
(a) It involves carbocation intermediate (b) the intermediate involves sp2 carbon
(c) Polar solvents accelerate the reaction (d) it involves inversion of configuration
 Topic: Alcohols, Phenols and Ethers

Section – A (2 Marks each)

Q1. Etherial solution of an organic compound ‘X’ when heated with Mg gave ‘Y’. ‘Y’ on treatment with CH 3 CHO
followed by acid hydrolysis gave 2-propanol. Identify the compound ‘X’. What is ‘Y’ known as ?

Q2. While separating a mixture of o- and p-nitrophenols by steam distillation name the isomer which is steam
volatile. Give reason.

Q3. Give equations of the following reactions :

(i) Oxidation of propan-1-ol with alkaline KMnO4 solution.
(ii) Bromine in CS2 with phenol.

Q4. Show how are the following alcohols prepared by the reaction of a suitable Grignard reagent on methanal?

Q5. Complete the following questions:

Q6. Predict the major product of acid catalysed dehydration of:

(i) 1-methylcyclohexanol (ii)
butan-1-ol

Q7. Arrange the following in the increasing order of the property indicated:
(i) p- nitrophenol, ethanol, phenol, p- cresol (acidic character)
(ii) propanol, propane, propanal (boiling point)

Q8. Give reasons:

(a) Alcohols are more soluble in water than the corresponding ethers.
(b) The pka value of o-nitrophenol is greater than the pka value of p-nitrophenol.

Section – B (3 Marks each)

Q9. How will you convert :

(i) Phenol to cyclohexanol (ii) Benzyl chloride to benzyl alcohol (iii) Anisole to phenol

Q10. Describe the following reactions with examples :

(i) Reimer-Teimann reaction (ii) Kolbe’s reaction (iii) Williamson Synthesis of ethers

Q11. Write the mechanism of acid dehydration of ethanol to yield ethene

Q12. Show how will you synthesise:

(i) 1-phenylethanol from a suitable alkene.
(ii) Cyclohexyl methanol using an alkyl halide by an SN2 reaction.
(iii) pentan-1-ol using a suitable alkyl halide?
Q13. Give the major products that are formed by heating each of the following ethers with HI.
 Q14. Predict the products of the
following reactions:

Q15. Phenol, C6 H5 OH when it first reacts with concentrated sulphuric acid, forms Y. The compound, Y is reacted
with concentrated nitric acid to form Z. Identify Y and Z and explain why phenol is not converted commercially
to Z by reacting it with conc. HNO3.

Q16. Account for the following:

(i) Protonation of phenols is difficult whereas ethanol easily undergoes protonation
(ii) Anisole on reaction with HI gives phenol and CH3-I as the main product and iodobenzene and CH3-OH
(iii) Preparation of ethers from secondary or tertiary alcohols by acid dehydration is not a suitable method.

Section – C (5 Marks each)

Q17. Name the reagents used in the following reactions:

(i) Oxidation of a primary alcohol to carboxylic acid.
(ii) Oxidation of a primary alcohol to aldehyde.
(iii) Bromination of phenol to 2,4,6-tribromophenol.
(iv) Benzyl alcohol to benzoic acid.
(v) Dehydration of propan-2-ol to propene..

Q18. An alcohol A (C4 H10O) on oxidation with acidified K2 Cr2 O7 gives carboxylic acid ‘B’ (C4 H8 O2 ). Compound ‘A’
when dehydrated with conc. H2 SO4 at 443 K gives compound ‘C’ with aqueous H2 SO4 . ‘C’ gives compound ‘D’
(C4 H10O) which is an isomer of ‘A’. Compound ‘D’ is resistant to oxidation but compound ‘A’ can be easily
oxidized. Identify A, B, C and D and write their structure.

Q19. Complete the following reactions:

 Section – D (4 marks Case based question)

Read the following paragraph and answer the following questions:

Q20. An owner of the paint company who was using ethanol as solvent noted that his stock of ethanol was misused
by his coworkers. To prevent this, he decided to add small amount of blue coloured compound (A) and another
nitrogen containing heterocyclic base (B) which gives a foul smell to the alcohol.

(i) Do you think that he took right decision and mention the value with this decision.

(ii) Write the names of the compounds (A) and (B).

(iii) What is denatured alcohol?

(iv) Consumption of methylated ethanol by a person can cause blindness and even death. How is methanol
poisoning treated?