Solution of Chapter 10. Haloalkanes and Haloarenes (Chemistry Part-II Book)

Write structures of the following compounds:

2-Chloro-3-methylpentane

Write structures of the following compounds:

1-Chloro-4-ethylcyclohexane

Write structures of the following compounds:

4-tert. Butyl-3-iodoheptane

Write structures of the following compounds:

1,4-Dibromobut-2-ene

Write structures of the following compounds:

1-Bromo-4-sec. butyl-2-methylbenzene.

Why is sulphuric acid not used during the reaction of alcohols with KI?

Write structures of different halogen derivatives of propane.

Among the isomeric alkanes of molecular formula C₅H₁₂, identify the one that on photochemical chlorination yields

A single monochloride.

Among the isomeric alkanes of molecular formula C₅H₁₂, identify the one that on photochemical chlorination yields

Three isomeric monochlorides.

Among the isomeric alkanes of molecular formula C₅H₁₂, identify the one that on photochemical chlorination yields

Four isomeric monochlorides.

Draw the structures of major monohalo products in each of the following reactions:

Draw the structures of major monohalo products in each of the following reactions:

Draw the structures of major monohalo products in each of the following reactions:

Draw the structures of major monohalo products in each of the following reactions:

Draw the structures of major monohalo products in each of the following reactions:

CH₃CH₂Br + NaI →

Draw the structures of major monohalo products in each of the following reactions:

Which alkyl halide from the following pairs would you expect to react more rapidly by an S_N2 mechanism? Explain your answer.

(i)

(ii)

(iii)

In the following pairs of halogen compounds, which compound undergoes faster S_N1 reaction?

(i)

(ii)

Identify A, B, C, D, E, R and R1 in the following:

Name the following halides according to IUPAC system and classify them as alkyl, allyl, benzyl (primary, secondary, tertiary), vinyl or aryl halides:

(i) (CH₃)₂CHCH(Cl)CH₃

(ii) CH₃CH₂CH(CH₃)CH(C₂H₅)Cl

(iii) CH₃CH₂C(CH₃)₂CH₂I

(iv) (CH₃)₃CCH₂CH(Br)C₆H₅

(v) CH₃CH(CH₃)CH(Br)CH₃

(vi) CH₃C(C₂H₅)₂CH₂Br

(vii) CH₃C(Cl)(C₂H₅)CH₂CH₃

(viii) CH₃CH=C(Cl)CH₂CH(CH₃)₂

(ix) CH₃CH=CHC(Br)(CH₃)₂

(x) p-ClC₆H₄CH₂CH(CH₃)₂

(xi) m-ClCH₂C₆H₄CH₂C(CH₃)₃

(xii) o-Br-C₆H₄CH(CH₃)CH₂CH₃CH₃

Give the IUPAC names of the following compounds:

CH₃CH(Cl)CH(Br)CH₃:2-Bromo-3-chlorobutane

Give the IUPAC names of the following compounds:

CHF₂CBrClF :1-bromo-1-chloro-1,2,2-trifluoroethane

Give the IUPAC names of the following compounds:

ClCH₂C≡CCH₂Br: 1-bromo-4-chlorobut-2-yne

Give the IUPAC names of the following compounds:

(CCl₃)₃CCl

Give the IUPAC names of the following compounds:

CH₃C(p-ClC₆H₄)₂CH(Br)CH₃

Give the IUPAC names of the following compounds:

(CH₃)₃CCH=CClC₆H₄I-p

Write the structures of the following organic halogen compounds.

2-Chloro-3-methylpentane

Write the structures of the following organic halogen compounds.

p-Bromochlorobenzene

Write the structures of the following organic halogen compounds.

1-Chloro-4-ethylcyclohexane

Write the structures of the following organic halogen compounds.

2-(2-Chlorophenyl)-1-iodooctane

Write the structures of the following organic halogen compounds.

2-Bromobutane

Write the structures of the following organic halogen compounds.

4-tert-Butyl-3-iodoheptane

Write the structures of the following organic halogen compounds.

1-Bromo-4-sec-butyl-2-methylbenzene

Write the structures of the following organic halogen compounds.

1,4-Dibromobut-2-ene

Which one of the following has the highest dipole moment?

(i) CH₂Cl₂ (ii) CHCl₃ (iii) CCl₄

A hydrocarbon C₅H₁₀ does not react with chlorine in dark but gives a single monochloro compound C₅H₉Cl in bright sunlight. Identify the hydrocarbon.

Write the isomers of the compound having formula C₄H₉Br.

Write the equations for the preparation of 1-iodobutane from

1-butanol

Write the equations for the preparation of 1-iodobutane from

1-chlorobutane

Write the equations for the preparation of 1-iodobutane from

but-1-ene.

What are ambident nucleophiles? Explain with an example.

Which compound in each of the following pairs will react faster in S_N2 reaction with –OH?

(i) CH₃Br or CH₃I (ii) (CH₃)₃CCl or CH₃Cl

Predict all the alkenes that would be formed by dehydrohalogenation of the following halides with sodium ethoxide in ethanol and identify the major alkene:

1-Bromo-1-methylcyclohexane

Predict all the alkenes that would be formed by dehydrohalogenation of the following halides with sodium ethoxide in ethanol and identify the major alkene:

2-Chloro-2-methylbutane

Predict all the alkenes that would be formed by dehydrohalogenation of the following halides with sodium ethoxide in ethanol and identify the major alkene:

2,2,3-Trimethyl-3-bromopentane.

How will you bring about the following conversions?

Ethanol to but-1-yne

How will you bring about the following conversions?

Ethane to bromoethene

How will you bring about the following conversions?

Propene to 1-nitropropane

How will you bring about the following conversions?

Toluene to benzyl alcohol

How will you bring about the following conversions?

Propene to propyne

How will you bring about the following conversions?

Ethanol to ethyl fluoride

How will you bring about the following conversions?

Bromomethane to propanone

How will you bring about the following conversions?

But-1-ene to but-2-ene

How will you bring about the following conversions?

1-Chlorobutane to n-octane

How will you bring about the following conversions?

Benzene to biphenyl.

Explain why

The dipole moment of chlorobenzene is lower than that of cyclohexylchloride?

Explain why

Alkyl halides, though polar, are immiscible with water?

Explain why

Grignard reagents should be prepared under anhydrous conditions?

Give the uses of Freon 12, DDT, carbon tetrachloride and iodoform.

Write the structure of the major organic product in each of the following reactions:

Write the structure of the major organic product in each of the following reactions:

(CH₃)₃CBr + KOH

Write the structure of the major organic product in each of the following reactions:

CH₃CH(Br)CH₂CH₃ + NaOH

Write the structure of the major organic product in each of the following reactions:

CH₃CH₂Br + KCN

Write the structure of the major organic product in each of the following reactions:

C₆H₅ONa + C₂H5Cl

Write the structure of the major organic product in each of the following reactions:

CH₃CH₂CH₂OH + SOCl₂

Write the structure of the major organic product in each of the following reactions:

CH₃CH₂CH = CH₂+ HBr

Write the structure of the major organic product in each of the following reactions:

CH₃CH = C(CH₃)₂ + HBr

Write the mechanism of the following reaction:

nBuBr + KCN nBuCN

Arrange the compounds of each set in order of reactivity towards S_N2 displacement:

2-Bromo-2-methylbutane, 1-Bromopentane, 2-Bromopentane

Arrange the compounds of each set in order of reactivity towards S_N2 displacement:

1-Bromo-3-methylbutane, 2-Bromo-2-methylbutane, 2-Bromo-3-methylbutane

Arrange the compounds of each set in order of reactivity towards S_N2 displacement:

1-Bromobutane, 1-Bromo-2,2 dimethylpropane, 1-Bromo-2-methylbutane, 1-Bromo-3-methylbutane.

Out of C₆H₅CH₂Cl and C₆H₅CHClC₆H₅, which is more easily hydrolysed by aqueous KOH.

p-Dichlorobenzene has higher m.p. than those of o- and m-isomers. Discuss.

How the following conversions can be carried out?

Propene to propan-1-ol

How the following conversions can be carried out?

Ethanol to but-1-yne

How the following conversions can be carried out?

1-Bromopropane to 2-bromopropane

How the following conversions can be carried out?

Toluene to benzyl alcohol

How the following conversions can be carried out?

Benzene to 4-bromonitrobenzene

How the following conversions can be carried out?

Benzyl alcohol to 2-phenylethanoic acid

How the following conversions can be carried out?

Ethanol to propanenitrile

How the following conversions can be carried out?

Aniline to chlorobenzene

How the following conversions can be carried out?

2-Chlorobutane to 3, 4-dimethylhexane

How the following conversions can be carried out?

2-Methyl-1-propene to 2-chloro-2-methylpropane

How the following conversions can be carried out?

Ethyl chloride to propanoic acid

How the following conversions can be carried out?

But-1-ene to n-butyliodide

How the following conversions can be carried out?

2-Chloropropane to 1-propanol

How the following conversions can be carried out?

Isopropyl alcohol to iodoform

How the following conversions can be carried out?

Chlorobenzene to p-nitrophenol

How the following conversions can be carried out?

2-Bromopropane to 1-bromopropane

How the following conversions can be carried out?

Chloroethane to butane

How the following conversions can be carried out?

Benzene to diphenyl

How the following conversions can be carried out?

tert-Butyl bromide to isobutyl bromide

How the following conversions can be carried out?

Aniline to phenylisocyanide

The treatment of alkyl chlorides with aqueous KOH leads to the formation of alcohols but in the presence of alcoholic KOH, alkenes are major products. Explain.

Primary alkyl halide C₄H₉Br (a) reacted with alcoholic KOH to give compound (b). Compound (b) is reacted with HBr to give (c) which is an isomer of (a). When (a) is reacted with sodium metal it gives compound (d), C₈H₁₈ which is different from the compound formed when n-butyl bromide is reacted with sodium. Give the structural formula of (a) and write the equations for all the reactions.

What happens when

n-butyl chloride is treated with alcoholic KOH,

What happens when

bromobenzene is treated with Mg in the presence of dry ether,

What happens when

chlorobenzene is subjected to hydrolysis,

What happens when

ethyl chloride is treated with aqueous KOH,

What happens when

methyl bromide is treated with sodium in the presence of dry ether,

What happens when

methyl chloride is treated with KCN?

Arrange each set of compounds in order of increasing boiling points.

(i) Bromomethane, Bromoform, Chloromethane, Dibromomethane.

(ii) 1-Chloropropane, Isopropyl chloride, 1-Chlorobutane.