WAEC 2022 Chemistry · Question 8
The IUPAC name for CHCHCHCHCLCHCHCHCH is
Options
- A.2, 4 - dimethyl - 3 - chlorohexane
- B.3, 5 - dimethyl - 4 - chlorohexane
- C.4 - chloro - 3, 5 - dirnethylhexane
- 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:
- Give the lowest set of locants to all substituents together.
- 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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