JAMB 2025 Chemistry · Question 88
(CH)CHCH(OH)CHC(CH) The IUPAC name of the compound above is
Options
- A.2,5,5-trimethylhexan-3-ol
- B.1,1-dimethylisopentanol
- C.1,1,4,4-pentamethylbutanol
- D.2,5-dimethylhexan-4-ol
Answer: A. 2,5,5-trimethylhexan-3-ol
Explanation written with AI and checked against the answer key
Analyze the question: We need the IUPAC name of (CH₃)₂CH–CH(OH)–CH₂–C(CH₃)₃.
Concept: To name an alcohol:
- Find the longest carbon chain that contains the carbon bearing the –OH.
- Number from the end that gives the –OH carbon the lowest possible number.
- Name and locate the substituents, then write them in the order: substituents, parent, then -ol with its position.
Solution:
Expand the structure:
(CH₃)₂CH – CH(OH) – CH₂ – C(CH₃)₃
- (CH₃)₂CH– is a carbon with two methyl groups.
- CH(OH) is the carbinol carbon.
- CH₂ is a methylene carbon.
- C(CH₃)₃ is a quaternary carbon with three methyls.
Longest chain: CH₃–CH–CH(OH)–CH₂–C–CH₃ gives 6 carbons, so the parent is hexane.
Numbering from the left (the CH₃ on the isopropyl end):
- C1: CH₃
- C2: CH (with a methyl branch)
- C3: CH(OH)
- C4: CH₂
- C5: C (with two methyl branches)
- C6: CH₃
Numbering from the right would put the –OH at C4, so the left-hand numbering is correct, giving –OH at C3.
Substituents: a methyl at C2 and two methyls at C5, so 2,5,5-trimethyl.
Name: 2,5,5-trimethylhexan-3-ol
Why the others are wrong:
- B and C use non-systematic or incorrectly built names.
- D numbers the chain so that –OH is at position 4, which breaks the lowest-number rule for the functional group.
Tip: In naming alcohols, the –OH gets the lowest number first, before any substituents. Then count the methyl branches carefully and use "tri" for three methyls (here 2, 5, 5).
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