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Chapter 10: Problem 21

Write down the IUPAC name of citric acid. O=C(O)CC(O)(CC(=O)O)C(=O)O (A) 2-Carboxy-2-hydroxy pentandioic acid (B) 2-Carboxy-3-hydroxy propane-1,3-dicarboxylic acid (C) 2 -hydroxy propane- \(1,2,3\)-tricarboxylic acid (D) Propane-1,2,3-tricarboxylic acid

Short Answer

Expert verified
The short answer is: \( 2\text{-hydroxy propane-}1,2,3\text{-tricarboxylic acid} \) (option C).

Step by step solution

01

Analyze the molecule structure from SMILES representation

SMILES (Simplified Molecular Input Line Entry System) representation of citric acid is given as: O=C(O)CC(O)(CC(=O)O)C(=O)O. It shows the following functional groups: - 3 carboxylic acid groups (COOH) - 1 hydroxyl group (OH)
02

Assigning positions to the functional groups

To assign positions to the functional groups, draw the structure of the citric acid molecule. \( O=C(O)CC(O)(CC(=O)O)C(=O)O \) becomes the structure: HOOC-CH2-C(OH)(COOH)-CH2-COOH From this structure, it's clear that the molecule has: - A hydroxyl group at carbon 2 - Carboxylic acid groups attached to carbons 1, 3 and 5.
03

Match the structure with the correct IUPAC name

Now, let's analyze the options: (A) 2-Carboxy-2-hydroxy pentandioic acid: This option indicates a pentane structure, which is incorrect. (B) 2-Carboxy-3-hydroxy propane-1,3-dicarboxylic acid: This option implies a carboxy group attached to carbon 2, which is incorrect. (C) 2-hydroxy propane-1,2,3-tricarboxylic acid: This option correctly matches our drawn structure for citric acid. It has a hydroxyl group at carbon 2 and carboxylic acid groups at carbons 1, 3, and 5. (D) Propane-1,2,3-tricarboxylic acid: This option is missing the hydroxyl group at carbon 2. The correct IUPAC name for citric acid is: 2-hydroxy propane-1,2,3-tricarboxylic acid (option C).

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Most popular questions from this chapter

For correct IUPAC name \(\mathrm{P}_{1}\)-methyl pent- \(\mathrm{P}_{2}\)-yne. How many pairs of \(\left(\mathrm{P}_{1}, \mathrm{P}_{2}\right)\) are possible? (A) 2 (B) 1 (C) \(\infty\) (D) 3

The IUPAC name of the following compound is CCC(C)C(C)CC (A) 2,3 -diethyl butane (B) 2 -ethyl- 3 -methyl pentane (C) 3-methyl-2-ethyl pentane (D) 3,4 -dimethyl hexane

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The general formula \(\mathrm{C}_{n} \mathrm{H}_{2 n-2}\) may represent (A) Allene (B) Alkyne (C) Bicycloalkane (D) Cycloalkene

The correct order for ortho xylene and para xylene is/are (A) \((\sigma \text {-bond })_{\text {oxylene }}>(\sigma \text {-bond })_{p \text {-xylene }}\) (B) \((\pi \text {-bond })_{o \text {-xylene }}<(\pi \text {-bond })_{p \text {-xylene }}\) (C) \(\mathrm{IHD}_{o \text {-xylene }}>(\pi \text {-bond })_{p \text {-xylene }}\) (D) \((\sigma \text {-bond })_{o \text {-xylene }}>(\pi \text {-bond })_{p \text {-xylene }}\)
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