ALKYL AND ARYL HALIDES
Very short answer type questions
Q.1. Which of the following is most reactive towards SN2 reaction : CH3Br, (CH3)2CHBr, (CH3)3 CBr.
Q.2. Organic halogen compounds used in industry as solvents are chlorides rather than bromides and iodides.
Q.3. How can you test the purity of chloroform?
Q.4. The use of chloroform as anaesthetic is decreasing. Why?
Q.5. What is the structure of an alkyl halide with molecular formula C4H9 Br is optically active.
Q.6. What is chirality?
Q.7. Which will have a higher boiling point :
l-chloroethane or 2-methyl -2- chlorobutane? Give reasons.
Q.8. An acid having molecular formula C3H5O2 Br is optically active. What is its structure.
Q.9. Which effect will the resonance have on the dipole moment of vinyl chloride?
CH2 = CH – Cl– ↔ CH2 – CH = Cl+
Q.10. Ethyl chloride is a gas, whereas ethyl iodide is a liquid at room temperature. Explain.
Q.11. What is meant by resolution?
Q.12. Write the IUPAC name of : CH3CH2CHCl2
Q.13. Derive the structure of : 2-chloro-2, 3-dimethyl pentane.
Short answer type questions
Q.1. Chloroform contains chlorine but gives no reaction with AgNO3 solution. Why?
Q.2. Why is chloroform stored in dark coloured bottles?
Q.3. Iodoform gives a precipitate with silver nitrate on heating while chloroform does not.
Q.4. Predict whether the following substitutions are likely to be SN1 or SN2
Q.5. A hydrocarbon C5H12 gives only the chlorination product. Identify the compound.
Q.6. Arrange the following halides in order of increasing SN2 reactivity :
CH3CH2Cl, CH3 Br, (CH3)2,CHCl, CH3Cl.
Q.7. Allyl chloride is more reactive than n-propyl chloride towards nucleophilic substitution reaction. Explain. Why?
Q.8. Which out of the two : 2-cyclopentanol or 3-cyclopentenol has chiral centre.
Q.9. 2-Hexulose has the formula
How many chiral carbon atoms does it have?
Q.10. What are enantiomers? Draw the structure of the possible enatiomers of 3-methylpent-1-ene.
Q.11 Why is sulphuric acid not used during the reaction of alcohols with KI?
Q.12. Write the structural isomers of the compound having formula C4H9Br.
Q.13. Covert
(i) Propene to prop-1-ol (ii) 1-Bromopropane to 2 Bromo propane
Q.14. Out of HCI (g) and SOCl2 which is preferred for converting ethanol into chloroethane?
Long answer type questions
Q.1. Write the various isomers of C7H7Cl containing benzene ring. Which of these has weakest C – CI bond?
Q.2. An alkyl halide (A) on reaction with magnesium in dry ether followed by treatment with ethanol gave 2- methylbutane. Write all the structure of [A].
Q.3. Among the isomeric alkanes of molecular formula C5H12 Identify the one that on photochemical chlorination yields:
(i) A single monochloride.
(ii) Three isomeric monochlorides, [Consider only structural isomers]
(iii) Four isomeric monochlorides. [Consider only structural isomers]
Q.4. Which alkyl halides from the following pairs would you expect to react more rapidly by SN2 mechanism? Explain your answer,
(i) CH3 CH2CH2CH2 Br or 
(ii) 
or 
Q.5. A hydrocarbon, does not react with chlorine in dark but gives a single monochloro compound C5H9Cl in sunlight. Identify the hydrocarbon.
Q.6. p-Dichlorobenzene has higher m.p. and solubility than those of o-and m-isomers. Discuss.
Q.7. Explain the following reaction :
n-BuBr +KCN EtOH-H2O n-BuCN
Q.8. Write the structure of the major organic product in each of the following reactions:
(a) CH3 CH2CH2 Cl + NaI (b) C6H5ONa + C2H5Cl →
(c) CH3CH = C (CH3)2 + HBr →
Q.9. Explain the formation of two products in the following reaction:
CH3 CH = CH CH2 Cl + H2O →
Very long answer type question
Q.1. Out of C6H5CH2Cl and C6H5CHCl C6H5, which is more easily hydrolysed by aquous KOH?
Q.2. Explain why
(a) the dipole moment of chlorobenzene is lower than that of cyclohexyl chloride,
(b) alkyl halides, though polar, are immiscible with water,
(c) Grignard reagents should be prepared under anhydrous conditions?
Q.3. Identity A. B, C, D. E, R and K in the following :
(i) 
(ii) 
(iii) 
Q.4. Give the structure of the main organic substitution product expected from the reaction of 1o bromobutane with
(i) (CH3)3N (ii) (CH3)2S
(iii) CH3COOAg (iv) LiAlH4
(v) C2H5ONa
