Chapter 10 - Haloalkanes and Haloarenes
Pages 285 - 307
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 dihalogen derivatives of propane.
Among the isomeric alkanes of molecular formula C5H12, identify the one that on photochemical chlorination yields
(i) A single monochloride.
(ii) Three isomeric monochlorides.
(iii) 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:
`CH_3CH_2Br + NaI ->`
Draw the structures of major monohalo products in each of the following reactions
Arrange each set of compounds in order of increasing boiling points
Bromomethane, Bromoform, Chloromethane, Dibromomethane.
Arrange each set of compounds in order of increasing boiling points.
1-Chloropropane, Isopropyl chloride, 1-Chlorobutane.
Which alkyl halide from the following pairs would you expect to react more rapidly by an SN2 mechanism? Explain your answer.
`CH_3CH_2CH_2CH_2Br` or
In the following pairs of halogen compounds, which compound undergoes faster SN1 reaction?
In the following pairs of halogen compounds, which compound undergoes faster SN1 reaction?
Identify A, B, C, D, E, R and R1 in the following:
Pages 310 - 312
Name the following halides according to IUPAC system and classify them as alkyl, allyl, benzyl (primary, secondary, tertiary), vinyl or aryl halides:
(CH3)2CHCH(Cl)CH3
Name the following halides according to IUPAC system and classify them as alkyl, allyl, benzyl (primary, secondary, tertiary), vinyl or aryl halides:
CH3CH2CH(CH3)CH(C2H5)Cl
Name the following halides according to IUPAC system and classify them as alkyl, allyl, benzyl (primary, secondary, tertiary), vinyl or aryl halides:
CH3CH2C(CH3)2CH2I
Name the following halides according to IUPAC system and classify them as alkyl, allyl, benzyl (primary, secondary, tertiary), vinyl or aryl halides:
(CH3)3CCH2CH(Br)C6H5
Name the following halides according to IUPAC system and classify them as alkyl, allyl, benzyl (primary, secondary, tertiary), vinyl or aryl halides:
CH3CH(CH3)CH(Br)CH3
Name the following halides according to IUPAC system and classify them as alkyl, allyl, benzyl (primary, secondary, tertiary), vinyl or aryl halides:
CH3C(C2H5)2CH2Br
Name the following halides according to IUPAC system and classify them as alkyl, allyl, benzyl (primary, secondary, tertiary), vinyl or aryl halides:
CH3C(Cl)(C2H5)CH2CH3
Name the following halides according to IUPAC system and classify them as alkyl, allyl, benzyl (primary, secondary, tertiary), vinyl or aryl halides:
CH3CH=C(Cl)CH2CH(CH3)2
Name the following halides according to IUPAC system and classify them as alkyl, allyl, benzyl (primary, secondary, tertiary), vinyl or aryl halides:
CH3CH=CHC(Br)(CH3)2
Name the following halides according to IUPAC system and classify them as alkyl, allyl, benzyl (primary, secondary, tertiary), vinyl or aryl halides:
p-ClC6H4CH2CH(CH3)2
Name the following halides according to IUPAC system and classify them as alkyl, allyl, benzyl (primary, secondary, tertiary), vinyl or aryl halides:
m-ClCH2C6H4CH2C(CH3)3
Name the following halides according to IUPAC system and classify them as alkyl, allyl, benzyl (primary, secondary, tertiary), vinyl or aryl halides:
o-Br-C6H4CH(CH3)CH2CH3
Give the IUPAC name of the following compounds:
CH3CH(Cl)CH(Br)CH3
Give the IUPAC name of the following compounds
CHF2CBrClF
Give the IUPAC name of the following compounds:
ClCH2C≡CCH2Br
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.
p-Bromochlorobenzene
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 structures of the following 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 SN2 reaction with OH−?
CH3Br or CH3I
Which compound in each of the following pairs will react faster in SN2 reaction with OH−?
(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?
Benzene to biphenyl.
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
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:
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
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:
CH3CH2CH = CH2 + HBr 
Write the structure of the major organic product in each of the following reactions:
`CH_3CH = C(CH_3)_2 + HBr ->`
Write the mechanism of the following reaction:
nBuBr + KCN 
nBuCN
Arrange the compounds of each set in order of reactivity towards SN2 displacement:
2-Bromo-2-methylbutane, 1-Bromopentane, 2-Bromopentane
Arrange the compounds of each set in order of reactivity towards SN2 displacement:
1-Bromo-3-methylbutane, 2-Bromo-2-methylbutane, 3-Bromo-2- methylbutane
Arrange the compounds of each set in order of reactivity towards SN2 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. and lower solubility 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?
Benzene to 4-bromonitrobenzene
How the following conversions can be carried out?
Benzyl alcohol to 2-phenylethanoic acid
How do you convert the following:
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
Write the main products 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.
Write the structure of the major organic product in each of the following reactions:
CH3CH2CH2OH + SOCl2 →