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Exercises · 8.7

Q.Give condensed and bond-line structural formulas and identify the functional group(s) present, if any, for:

(a) 2,2,4-Trimethylpentane
(b) 2-Hydroxy-1,2,3-propanetricarboxylic acid
(c) Hexanedial.
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(a) 2,2,4-Trimethylpentane is a branched alkane — no functional group. (b) 2-Hydroxy-1,2,3-propanetricarboxylic acid (citric acid) has one alcohol and three carboxylic-acid groups. (c) Hexanedial is a dialdehyde — two aldehyde groups.

Decode each IUPAC name into its carbon skeleton, write the condensed formula, sketch the bond-line (skeletal) form, and read off the functional groups.

(a) 2,2,4-Trimethylpentane

A five-carbon (pentane) main chain carrying two methyl branches on C-2 and one on C-4.

Condensed formula: (CH3)3C–CH2–CH(CH3)–CH3\text{(CH}_3)_3\text{C--CH}_2\text{--CH(CH}_3)\text{--CH}_3

Bond-line: a five-carbon zig-zag; two extra bonds meet at the second carbon (a quaternary carbon) and one extra bond at the fourth carbon. Every vertex and chain end is a carbon, hydrogens implicit.

Functional group: none — it is a saturated hydrocarbon (alkane).

(b) 2-Hydroxy-1,2,3-propanetricarboxylic acid

A three-carbon (propane) backbone bearing a –COOH\text{--COOH} on each of C-1, C-2 and C-3 and an –OH\text{--OH} on C-2. This is citric acid.

Condensed formula: HOOC–CH2–C(OH)(COOH)–CH2–COOH\text{HOOC--CH}_2\text{--C(OH)(COOH)--CH}_2\text{--COOH}

Bond-line: the central carbon carries an –OH\text{--OH} and a –COOH\text{--COOH}; each of the two arms is a –CH2–COOH\text{--CH}_2\text{--COOH}, the carboxyls drawn as CO2H\text{CO}_2\text{H}.

Functional groups: three carboxylic-acid (–COOH\text{--COOH}) groups and one alcohol (–OH\text{--OH}).

(c) Hexanedial

A six-carbon (hexane) chain with an aldehyde (–CHO\text{--CHO}) at each end (the "-dial" suffix; aldehydes must be terminal).

Condensed formula: OHC–(CH2)4–CHO\text{OHC--(CH}_2)_4\text{--CHO}

Bond-line: a six-carbon zig-zag with a carbonyl (= ⁣O=\!\text{O}) at each terminal carbon. …

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