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In primary (1°) haloalkanes, the carbon that carries the halogen atom is only attached to one other alkyl group. An example is chloroethane (CH 3 CH 2 Cl). In secondary (2°) haloalkanes, the carbon that carries the halogen atom has two C–C bonds. In tertiary (3°) haloalkanes, the carbon that carries the halogen atom has three C–C bonds.
The reaction involves a carbocation intermediate and is commonly seen in reactions of secondary or tertiary alkyl halides under strongly basic conditions or, under strongly acidic conditions, with secondary or tertiary alcohols. With primary and secondary alkyl halides, the alternative S N 2 reaction occurs.
Experiments have shown that all halogenation produces a mixture of all possible isomers, indicating that all hydrogen atoms are susceptible to reaction. The mixture produced, however, is not statistical: Secondary and tertiary hydrogen atoms are preferentially replaced due to the greater stability of secondary and tertiary free-radicals.
Secondary alcohols react within five or so minutes (depending on their solubility). Primary alcohols do not react appreciably with Lucas reagent at room temperature. [ 3 ] Hence, the time taken for turbidity to appear is a measure of the reactivity of the class of alcohol, and this time difference is used to differentiate among the three ...
The experimental relative chlorination rates at primary, secondary, and tertiary positions match the corresponding radical species' stability: tertiary (5) > secondary (3.8) > primary (1). Thus any single chlorination step slightly favors substitution at the carbon already most substituted.
In addition, each position on an alkyl chain can be described according to how many other carbon atoms are attached to it. The terms primary, secondary, tertiary, and quaternary refer to a carbon attached to one, two, three, or four other carbons respectively.
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The alkoxide (or aryloxide) may be primary and secondary. Tertiary alkoxides tend to give elimination reaction because of steric hindrance. The alkylating agent, on the other hand is most preferably primary. Secondary alkylating agents also react, but tertiary ones are usually too prone to side reactions to be of practical use.