AS 9701 Organic Chemistry Part 13 | Halogenoalkanes | Nucleophilic Substitution

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15 Halogen compounds
15.1 Halogenoalkanes
Learning outcomes
Candidates should be able to:
1 recall the reactions (reagents and conditions) by which halogenoalkanes can be produced:
(a) the free-radical substitution of alkanes by Cl 2 or Br2 in the presence of ultraviolet light, as exemplified by
the reactions of ethane
(b) electrophilic addition of an alkene with a halogen, X2, or hydrogen halide, HX(g), at room temperature
(c) substitution of an alcohol, e.g. by reaction with HX or KBr with H2SO4 or H3PO4; or with PCl 3 and heat;
or with PCl 5; or with SOCl 2
2 classify halogenoalkanes into primary, secondary and tertiary
3 describe the following nucleophilic substitution reactions:
(a) the reaction with NaOH(aq) and heat to produce an alcohol
(b) the reaction with KCN in ethanol and heat to produce a nitrile
(c) the reaction with NH3 in ethanol heated under pressure to produce an amine
(d) the reaction with aqueous silver nitrate in ethanol as a method of identifying the halogen present as
exemplified by bromoethane
15.1 Halogenoalkanes (continued)
4 describe the elimination reaction with NaOH in ethanol and heat to produce an alkene as exemplified by
bromoethane
5 describe the SN1 and SN2 mechanisms of nucleophilic substitution in halogenoalkanes including the inductive
effects of alkyl groups
6 recall that primary halogenoalkanes tend to react via the SN2 mechanism; tertiary halogenoalkanes via the
SN1 mechanism; and secondary halogenoalkanes by a mixture of the two, depending on structure
7 describe and explain the different reactivities of halogenoalkanes (with particular reference to the relative
strengths of the C–X bonds as exemplified by the reactions of halogenoalkanes with aqueous silver nitrates

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