What is the IUPAC name of tertiarybutyl alcohol?
- (a)1-propylpropan-3-ol
- (b)1-ethylpropan-3-ol
- (c)1-Methylpropan-3-ol
- (d)2-Methylpropan-2-ol
Answer
Why
Correct — D. tert-Butyl alcohol is (CH₃)₃C–OH — one carbon carrying the –OH and three methyl groups.
Rule: the parent chain is the longest chain through the carbon that bears the –OH.
Longest chain here = three carbons → propane.
The third methyl becomes a methyl branch.
–OH takes the lower locant → C2, methyl at C2.
Name: 2-methylpropan-2-ol → option (d).
The prefix tert is itself the clue: the carbinol carbon is joined to three other carbons.
Why the others are wrong
- (a)1-propylpropan-3-ol — Not a legal name. Write it out — propyl on C1 of propane, –OH on C3 — and the chain through the –OH runs six carbons, so the compound is hexan-1-ol, a primary alcohol.
- (b)1-ethylpropan-3-ol — Five carbons, so it is out before you check the class. Ethyl on propane gives pentan-1-ol; tert-butyl alcohol has four carbons in all.
- (c)1-Methylpropan-3-ol — Primary, and 'tert' rules that out. Methyl on propane is butan-1-ol misnumbered — a genuine isomer of tert-butyl alcohol, both C₄H₁₀O, but its –OH sits on a terminal carbon.
Concept
Two rules settle almost every alcohol-naming question.
Parent chain — the longest carbon chain containing the carbon that bears the –OH. Anything left over is a substituent.
Numbering — the chain is numbered so the –OH takes the lowest possible locant. Substituent numbers follow from that choice, never the reverse.
The four alcohols of formula C₄H₁₀O are worth memorising outright:
n-butyl alcohol = butan-1-ol
sec-butyl alcohol = butan-2-ol
isobutyl alcohol = 2-methylpropan-1-ol
tert-butyl alcohol = 2-methylpropan-2-ol
Options (a) to (c) are not merely wrong answers — none of them is a legal IUPAC name. Each keeps a three-carbon parent when a longer chain through the –OH exists.
Key facts
- tert-Butyl alcohol, (CH₃)₃C–OH, is 2-methylpropan-2-ol in IUPAC nomenclature.
- An alcohol is primary, secondary or tertiary according to whether the –OH carbon is bonded to one, two or three other carbons.
- The parent chain is the longest chain containing the –OH carbon, and that carbon takes the lowest locant.
- C₄H₁₀O has four alcohol isomers: butan-1-ol, butan-2-ol, 2-methylpropan-1-ol and 2-methylpropan-2-ol.
Study next
Common traps
- Naming the longest chain in the molecule instead of the longest chain through the –OH carbon.
- Fixing the substituent's number first and letting the –OH take whatever locant is left.
- Picking the most complicated-looking option because the common name sounds complicated.
SSC's chemistry in General Awareness stays at naming and everyday identity — a common name to convert, a formula to match, a use to recall. Never mechanisms.
Related PYQs
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