Chemistry
Alkyl Halides
4,932 words, 10 sections
This chapter is unit 15 of the PMDC MDCAT chemistry syllabus, Alkyl Halides, and it is where organic chemistry stops being about naming and starts being about mechanism. The bank holds 137 distinct questions drawn from it across 71 official papers between 2002 and 2026, set by six boards, and the 696 active questions here sit at a mean item difficulty of 1.76. Nucleophilic substitution alone accounts for 70 of those questions, 42 more sit on nomenclature and reactivity, and 25 on elimination. Almost everything on the paper turns on one idea, that the carbon-halogen bond is polar and can be broken in two directions, towards substitution or towards elimination, and the examiner keeps asking which one a given reagent chooses. A student who has mastered the chapter can name any haloalkane, predict whether a given substrate meets a given reagent as , , or , rank the halides by reactivity, and use a Grignard reagent to build a specified alcohol.
An alkyl halide is a halogen derivative of an alkane: one or more hydrogens of a saturated hydrocarbon have been replaced by a halogen, and the monohalo family is written , with the general formula . Count the halogens first. A molecule carrying one halogen is a monohaloalkane, two gives a dihaloalkane, three a trihaloalkane, and more a polyhaloalkane. Then classify by the carbon that holds the halogen. That carbon is primary when it carries one alkyl group or none, secondary when it carries two, and tertiary when it carries three. The class belongs to that carbon, never to the molecule's overall shape, which is why neopentyl chloride is a primary alkyl halide even though its skeleton is branched: the halogen sits on a group whose only carbon neighbour is the quaternary centre.
Two naming systems run side by side. The common system names the alkyl group first and the halide second, so is ethyl chloride, and a straight-chain group takes the prefix n-, as in n-butyl bromide. IUPAC treats the halogen as a substituent on the alkane: choose the longest continuous chain that contains the halogen, number it so the halogen has the lowest locant, and write the halogen as a prefix, chloro for and bromo for . That gives 1-bromobutane, 2-bromo-3-methylbutane and 2-methyl-2-chloropropane. Both systems are accepted, and the exam leans on the common names for simple members. Halothane, the inhaled anaesthetic, is , a halo derivative of ethane and not of methane.
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