Q.Give the structure of 2-chloro-3-methylpentane.
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🔒 Start your 14-day free trial to unlock the full solution →Concept understanding — Nomenclature of Haloalkanes
Haloalkanes carry two naming systems side by side. The common system names the alkyl group first, then adds 'halide' -- methyl iodide, ethyl bromide, tert-butyl chloride, neo-pentyl bromide -- and is still widely used for simple, well-known compounds. The IUPAC system treats the halogen exactly like any other substituent: find the longest chain containing the halogen-bearing carbon, number it to give the lowest locant set overall, and cite the halogen as a fluoro-/chloro-/bromo-/iodo- prefix in alphabetical order alongside any other substituents, e.g. CH3-CH(Cl)-CH2-CH3 is 2-chlorobutane, and (CH3)3C-CH2-Br is 1-bromo-2,2-dimethylpropane (common name neopentyl bromide). Two refinements matter for exam questions: (1) when the halogen sits on an unsaturated chain, the double/triple bond gets priority for the lowest locant over the halogen, e.g. CH2=C(CH3)-CH2-Cl is numbered from the alkene end to give 3-chloro-2-methylprop-1-ene, not the other way round; (2) for a polyhalogenated ring or chain, every halo …
Numbering the five-carbon pentane chain so that position 2 carries the chlorine substituent and position 3 carries the methyl branch reproduces exactly what …
2-chloro-3-methylpentane is a 5-carbon chain (pentane) with Cl on C2 and a methyl branch on C3.
Numbering the parent pentane chain C1 to C5:
- C1: CH₃
- C2: CHCl (chloro substituent here)
- C3: CH(CH₃) (methyl branch here)
- C4: CH₂
- C5: CH₃ …
- CBSE 2026Set ANNUAL1 markQ.Give the structure of 2-chloro-3-methylpentane.
›Reveal solutionSolution
2-chloro-3-methylpentane is a 5-carbon chain (pentane) with Cl on C2 and a methyl branch on C3.
Numbering the parent pentane chain C1 to C5:
- C1: CH₃
- C2: CHCl (chloro substituent here)
- C3: CH(CH₃) (methyl branch here)
- C4: CH₂
- C5: CH₃ …
- CBSE 2024Set ANNUAL1 markQ.Write the structure of the following organic halogen compound. 1, 4-Dibromobut-2-ene
›Reveal solutionSolution
But-2-ene is numbered C1-C4 with the double bond at C2=C3; substituting Br at C1 and C4 gives the structure.
Step 1: Draw the parent chain but-2-ene (4 carbons, double bond between C2 and C3):
CH3-CH=CH-CH3, numbered C1-C2=C3-C4.
Step 2: '1,4-dibromo' means a bromine substituent replaces one H each at C1 and C4.
Step 3: Combine — the structure is: …
- CBSE 2023Set ANNUAL1 markQ.Write structural formula and IUPAC name of chloroform.
›Reveal solutionSolution
Chloroform's structural formula is CHCl₃ and its IUPAC name is trichloromethane.
Chloroform is a haloalkane in which three of the four hydrogen atoms of methane (CH₄) are replaced by chlorine atoms.
Structural formula: three Cl atoms and one H atom attached to a single central carbon — written linearly as CHCl₃.
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- CBSE 2021Set OC1 markQ.Write the IUPAC name of CH3−CH(Cl)−CH(CH3)−CH2−CH3 (drawn with the Cl below the second carbon and the CH3 branch above the third carbon of the chain).
›Reveal solutionSolution
The parent chain is pentane, bearing a chlorine and a methyl group on adjacent carbons; numbering from the end that gives the lower locant set names it 2-chloro-3-methylpentane.
Working out the IUPAC name
The given compound CH3−CH(Cl)−CH(CH3)−CH2−CH3 has a continuous 5-carbon chain, so the parent hydrocarbon is pentane.
Numbering from the left: C1 (CH3), C2 (bears Cl), C3 (bears CH3), C4 (CH2), C5 (CH3) → substituent locants {2 (chloro), 3 (methyl)}.
Numbering from the right instead would give locants {3 (methyl), 4 (chloro)}.
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- CBSE 2018Set ANNUAL1 markQ.Write IUPAC name of CH3.C(C2H5)2.CH2Br.
›Reveal solutionSolution
IUPAC naming always starts by finding the LONGEST continuous carbon chain in the structure; here that chain runs through both ethyl branches (5 carbons, a pentane), leaving -CH3 and -CH2Br as two substituents on its middle carbon.
STRUCTURE: CH3-C(C2H5)2-CH2Br is a central carbon bonded to four groups: a -CH3, two -C2H5 (ethyl) groups, and a -CH2Br group. Total: 7 carbon atoms, 1 bromine.
STEP 1 - Find the longest chain: Tracing a path through the two ethyl branches AND the central carbon gives a continuous run of 5 carbons: CH3-CH2-C(...)-CH2-CH3. This is longer than the alternative path through the central carbon plus the -CH2Br arm (only 4 carbons). By the rule 'always select the longest possible continuous chain first,' the parent chain is this 5-carbon PENTANE, with the original central carbon becoming C-3 (the middle carbon, by symmetry).
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