Ch. 3 - An Introduction to Organic Compounds:Nomenclature, Physical Properties, and Structure

Bruice8th EditionOrganic ChemistryISBN: 9780135213711Not the one you use?Change textbook

Bruice 8th Edition

Ch. 3 - An Introduction to Organic Compounds:Nomenclature, Physical Properties, and Structure

Problem 65

Chapter 4, Problem 65

Ansaid and Motrin belong to the group of drugs known as nonsteroidal anti-inflammatory drugs (NSAIDs). Both are only slightly soluble in water, but one is a little more soluble than the other. Which of the drugs has the greater solubility in water?

Verified step by step guidance

Begin by examining the chemical structures of Ansaid and Motrin. Look for functional groups that can interact with water molecules, such as hydroxyl (-OH), carboxyl (-COOH), or amine (-NH2) groups.

Consider the polarity of each molecule. Polar molecules tend to be more soluble in water due to their ability to form hydrogen bonds with water molecules. Identify any polar functional groups in each drug.

Evaluate the overall molecular size and shape. Larger molecules or those with extensive hydrophobic regions may have reduced solubility in water.

Analyze the presence of any ionic groups. Ionic compounds generally have higher solubility in water due to the strong electrostatic interactions with water molecules.

Compare the solubility-enhancing features of each drug. The drug with more polar or ionic groups, or fewer hydrophobic regions, is likely to have greater solubility in water.

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Key Concepts

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

Solubility

Solubility refers to the ability of a substance to dissolve in a solvent, typically water. It is influenced by factors such as temperature, pressure, and the chemical nature of the solute and solvent. In organic chemistry, understanding solubility is crucial for predicting how compounds will behave in biological systems and their effectiveness as drugs.

Nonsteroidal Anti-Inflammatory Drugs (NSAIDs)

NSAIDs are a class of medications that reduce inflammation, pain, and fever. They work by inhibiting enzymes called cyclooxygenases (COX), which are involved in the production of prostaglandins, compounds that mediate inflammation. Knowledge of NSAIDs is essential for understanding their pharmacological properties and therapeutic uses.

Chemical Structure and Polarity

The chemical structure of a compound, including its functional groups and overall polarity, significantly affects its solubility in water. Polar molecules tend to be more soluble in polar solvents like water, while nonpolar molecules are less soluble. Analyzing the structures of Ansaid and Motrin will help determine which has greater solubility based on their polarity.

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Related Practice

Textbook Question

A student was given the structural formulas of several compounds and was asked to give them systematic names. How many did the student name correctly? Correct those that are misnamed.

c. 5-methylcyclohexanol

d. 1,1-dimethyl-2-cyclohexanol

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Textbook Question

Draw a picture of the hydrogen bonding in methanol.

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Textbook Question

Which has

i. the greater density: heptane or octane?

j. the higher boiling point: isopentyl alcohol or isopentylamine?

k. the higher boiling point: hexylamine or dipropylamine?

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Textbook Question

Which has

h. the higher boiling point: diethyl ether or butyl alcohol?

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Textbook Question

c. Draw Newman projections of the two conformers of the trans isomer.

d. Which of the conformers predominates at equilibrium?

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Textbook Question

A student was given the structural formulas of several compounds and was asked to give them systematic names. How many did the student name correctly? Correct those that are misnamed.

a. 4-bromo-3-pentanol

b. 2,2-dimethyl-4-ethylheptane

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