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Chapter 26: Problem 37

Supply condensed structural formulas for the following substances. (a) 2,4,6 -trinitrotoluene (TNT-an explosive) (b) methyl salicylate (oil of wintergreen) [Hint: Salicylic acid is \(o \text { -hydroxybenzoic acid. }]\) (c) 2 -hydroxy-1,2,3-propanetricarboxylic acid (citric \(\left.\operatorname{acid}, \mathrm{C}_{6} \mathrm{H}_{8} \mathrm{O}_{7}\right)\).

Short Answer

Expert verified
(a) 2,4,6 -trinitrotoluene = \(CH_3-C_6H_2(NO_2)_3\)\n(b) methyl salicylate = \(O=C(OCH_3)-C_6H_4-OH\)\n(c) 2 -hydroxy-1,2,3-propanetricarboxylic acid = \(-COOH-CH(OH)-COOH-CH_2-COOH\)

Step by step solution

01

Writing Structure for 2,4,6 -trinitrotoluene

Toluene is a methyl group attached to a benzene ring. Trinitrotoluene has three nitro groups \(-NO_2\).Their positions are indicated by the numbers 2,4 and 6, meaning positions opposite to the methyl groups on the Benzene ring. Thus, we have \(CH_3-C_6H_2(NO_2)_3\)
02

Writing Structure for methyl salicylate

Salicylic acid is ortho-hydroxybenzoic acid which means a carboxylic acid \(-COOH\) and a hydroxyl group \(-OH\) on adjacent positions of a benzene ring. Methyl salicylate replaces the hydrogen in the carboxylic group with a methyl \(-CH_3\) group, giving the formula \(O=C(OCH_3)-C_6H_4-OH.\)
03

Writing Structure for 2 -hydroxy-1,2,3-propanetricarboxylic acid

Propane indicates a 3-carbon backbone. The 1,2,3-tricarboxylic acid indicates three carboxylic acid groups on every carbon atom. The 2-hydroxy indicates a hydroxyl group attached to the second carbon atom. The formula thus becomes \(-COOH-CH(OH)-COOH-CH_2-COOH.\)

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