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Ch. 2 - Acids and Bases; Functional Groups
Wade - Organic Chemistry 9th Edition
Wade9th EditionOrganic ChemistryISBN: 9780135213728Not the one you use?Change textbook
All textbooksWade 9th EditionCh. 2 - Acids and Bases; Functional GroupsProblem 57c
Chapter 2, Problem 57c

Many naturally occurring compounds contain more than one functional group. Identify the functional groups in the ­following compounds:
d. Thyroxine is the principal thyroid hormone.

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1
Begin by examining the molecular structure of thyroxine. Look for characteristic groupings of atoms that correspond to known functional groups.
Identify any hydroxyl groups (OH) in the structure. These are typically found as an -OH bonded to a carbon atom and are indicative of alcohols.
Look for any carboxyl groups (COOH). These consist of a carbon double-bonded to an oxygen and single-bonded to a hydroxyl group, characteristic of carboxylic acids.
Check for the presence of amine groups (NH2 or NH). These are nitrogen atoms bonded to hydrogen atoms and are common in amino acids and proteins.
Identify any ether groups (R-O-R'). These are oxygen atoms bonded to two alkyl or aryl groups, which are common in many organic compounds.

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Key Concepts

Here are the essential concepts you must grasp in order to answer the question correctly.

Functional Groups

Functional groups are specific groups of atoms within molecules that are responsible for the characteristic chemical reactions of those molecules. In organic chemistry, identifying functional groups is crucial as they determine the properties and reactivity of the compound. Common examples include hydroxyl, carboxyl, amino, and carbonyl groups.
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Thyroxine Structure

Thyroxine, a principal thyroid hormone, is an organic compound with a complex structure that includes multiple functional groups. Understanding its structure involves recognizing the presence of phenolic hydroxyl groups, ether linkages, and amine groups, which contribute to its biological activity and solubility properties.
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Chemical Reactivity and Biological Function

The chemical reactivity of thyroxine is influenced by its functional groups, which play a role in its interaction with biological systems. These interactions are essential for its function as a hormone, affecting metabolism and growth. Recognizing how these groups contribute to its reactivity helps in understanding its mechanism of action in the body.
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Related Practice
Textbook Question

The pKa of ascorbic acid (vitamin C, page 55) is 4.17, showing that it is slightly more acidic than acetic acid (CH3COOH, pKa 4.74).

a. Show the four different conjugate bases that would be formed by deprotonation of the four different OH groups in ascorbic acid.

b. Compare the stabilities of these four conjugate bases, and predict which OH group of ascorbic acid is the most acidic.

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Textbook Question

The pKa of ascorbic acid (vitamin C, page 55) is 4.17, showing that it is slightly more acidic than acetic acid (CH3COOH, pKa 4.74).

c. Compare the most stable conjugate base of ascorbic acid with the conjugate base of acetic acid, and suggest why these two compounds have similar acidities, even though ascorbic acid lacks the carboxylic acid (COOH) group.

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Textbook Question

Many naturally occurring compounds contain more than one functional group. Identify the functional groups in the ­following compounds:

a. Penicillin G is a naturally occurring antibiotic.

b. Dopamine is the neurotransmitter that is deficient in Parkinson’s disease.

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