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Write Brief Answer · Q38

Q.Give the IUPAC names of the following compounds.

(i) (CH3)2CH-CH2-CH(CH3)-CH(CH3)2
(ii) CH3-CH(CH3)-CH(Br)-CH3
(iii) CH3-O-CH3
(iv) CH3-CH2-CH(OH)-CHO
(v) CH2=CH-CH=CH2
(vi) CH3-C≡C-CH(Cl)-CH3
(vii) CH3-CH=CH-CH2Br, drawn with the CH3 and the CH2Br chain both on the same (lower) side of the double bond and both alkene-carbon H's on the upper side (a cis/Z-configured allylic bromide)
(viii) HOOC-CH2-CH2-CH2-CO-CH3
(ix) CH3-CH2-CH2-CH(CH=CH2)-CH(CH2CH3)-CH2-CH3 (a heptane-type chain bearing a vinyl (-CH=CH2) branch on one carbon and an ethyl branch on the adjacent carbon, with an ethyl group also continuing the chain)
(x) (CH3)3C-CH=C(CH3)-CH3
(xi) C6H5-CH(NH2)-CH(CH3)2
(xii) CH3-CO-CH2-C(CH3)2-CN
(xiii) CH3-CH2-O-CH(CH3)-CH3 (ethyl isopropyl ether; printed twice under the same "(xiii)" label in the source textbook, an apparent numbering slip)
(xiv) a benzene ring bearing -NO2 and two -CH3 groups, with one -CH3 ortho to -NO2 and the other -CH3 meta to -NO2 (and para to the first -CH3)
(xv) OHC-CH(CH3)-CH(CH3)-CH(Br)-CH2-CH3
(xvi) C6H5-CO-CH3 (acetophenone; printed twice under the same "(xvi)" label in the source textbook, an apparent numbering slip)
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Step 1 (i). (CH3)2CH-CH2-CH(CH3)-CH(CH3)2: longest chain 5C with methyls at C2 and C4 -> 2,4-dimethylpentane.

Step 2 (ii). CH3-CH(CH3)-CH(Br)-CH3: 4C chain, methyl at C2 (from the COOH-free lowest-locant rule, giving bromo priority for lowest number since it is cited first alphabetically among equal-priority substituents) -> 3-bromo-2-methylbutane (bromo and methyl at adjacent locants 2,3; numbering chosen so the substituent cited first alphabetically, bromo, need not get the lower number here since the true tie-break is the lowest LOCANT SET {2,3} either way -- 2-methyl-3-bromobutane and 3-bromo-2-methylbutane name the same molecule, alphabetical citation gives 3-bromo-2-methylbutane).

Step 3 (iii). CH3-O-CH3: the simplest ether, IUPAC methoxymethane (common name dimethyl ether).

Step 4 (iv). CH3-CH2-CH(OH)-CHO: 4C chain, principal group CHO fixes C1, OH at C3 -> 3-hydroxybutanal... re-counting the chain (CH3-CH2-CH(OH)-CHO is 4 carbons: C1=CHO, C2=CH2, C3=CH(OH)... wait the OH sits on the carbon adjacent to CHO) -> 3-hydroxybutanal is for a 4-carbon count; matching the drawn 5-atom (C1 CHO, C2 CH(OH), C3 CH2, C4 CH3) reading gives 3-hydroxypentanal only if 5 carbons are present -- here CH3-CH2-CH(OH)-CHO has exactly 4 carbons (CHO, CH(OH), CH2, CH3), so the correct name is 3-hydroxybutanal.

Step 5 (v). CH2=CH-CH=CH2: 4C chain, double bonds at 1,3 -> buta-1,3-diene.

Step 6 (vi). CH3-C≡C-CH(Cl)-CH3: 5C chain, triple bond needs the lower locant over the chloro substituent per the unsaturation-before-substituent rule, numbering from the triple-bond end gives yne at C2 and chloro at C4 -> 4-chloropent-2-yne.

Step 7 (vii). CH3-CH=CH-CH2Br, drawn with CH3 and the CH2Br chain on the same side (Z-configuration): but-2-ene chain, bromo at C1 (or C4 depending on direction; numbering from the Br end gives lowest locant to the substituent since there is no higher-priority group) -> (Z)-1-bromobut-2-ene.

Step 8 (viii). HOOC-CH2-CH2-CH2-CO-CH3: 6C chain, COOH fixes C1, ketone at C5 -> 5-oxohexanoic acid.

Step 9 (ix). A heptane-type chain bearing a vinyl branch on one carbon and an ethyl branch on the adjacent carbon (with the chain continuing as ethyl on both ends): naming the longest chain through the propyl and ethyl-bearing ends gives 4-ethyl-3-vinylheptane (vinyl cited as a substituent prefix for -CH=CH2).

Step 10 (x). (CH3)3C-CH=C(CH3)-CH3: extending through a terminal methyl (as in Q9's logic) gives a 5C chain, double bond at C2, gem-dimethyl at C4, one more methyl at C2 -> 2,4,4-trimethylpent-2-ene.

Step 11 (xi). C6H5-CH(NH2)-CH(CH3)2: propan-1-amine chain with phenyl and the two branch methyls resolving to an isopropyl-bearing carbon -> 2-methyl-1-phenylpropan-1-amine. …

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