WAEC 2022 Chemistry · Question 8

The IUPAC name for CH3_{3}CHCH3_{3}CHCLCHCH3_{3}CH2_{2}CH3_{3} is

Options

  1. A.2, 4 - dimethyl - 3 - chlorohexane
  2. B.3, 5 - dimethyl - 4 - chlorohexane
  3. C.4 - chloro - 3, 5 - dirnethylhexane
  4. D.3 - chloro - 2, 4 - dimethylhexane

Answer: D. 3 - chloro - 2, 4 - dimethylhexane

Explanation written with AI and checked against the answer key

Analyze the question

The formula is CH₃CH(CH₃)CHClCH(CH₃)CH₂CH₃. We need to find the main chain, number it, and name the substituents.

Structure

Writing it out carbon by carbon:

  • C1: CH₃
  • C2: CH (with a CH₃ branch)
  • C3: CHCl
  • C4: CH (with a CH₃ branch)
  • C5: CH₂
  • C6: CH₃

The longest chain has 6 carbons, so the parent is hexane. The substituents are two methyl groups and one chlorine.

Numbering

The rules for numbering are:

  1. Give the lowest set of locants to all substituents together.
  2. Name the substituents in alphabetical order (chloro before methyl; "di" is ignored for alphabetising).
  • Numbering from the left: substituents are at 2 (methyl), 3 (chloro), 4 (methyl), so the locant set is {2,3,4}.
  • Numbering from the right: C1 = CH₃, C2 = CH₂, C3 = CH(CH₃), C4 = CHCl, C5 = CH(CH₃), C6 = CH₃. The locants are {3,4,5}.

{2,3,4} is lower, so we number from the left.

Name

  • Chloro at C3
  • Methyl at C2 and C4

Alphabetical order puts chloro first: 3-chloro-2,4-dimethylhexane

Checking the options

  • A: The locants are right, but the alphabetical order is wrong (it lists methyl before chloro).
  • B: The numbering is wrong.
  • C: The numbering is wrong (4-chloro-3,5-dimethyl).
  • D: 3-chloro-2,4-dimethylhexane. This is correct.

Tip: First find the longest chain. Then number so the substituent locants are as low as possible, and write the names alphabetically (ignoring di-, tri-). Option A is a common trap: the numbers are correct, but the name is not in alphabetical order.

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