ALCOHOLS

Chapter 21

Alcohols

Alcohols occur widely in nature and have many industrial, pharmaceutical, and biological applications:
Fuel

Additive Industrial Solvents Beverages Food Flavoring and Supplements

Objectives

To be able to name simple alcohols according to IUPAC system

To be able to know the general properties of alcohols

Functional Groups and Classes of Organic Compounds

Functional group an atom or group of atoms that is responsible for specific properties of an organic compound Bonds in the functional group are usually the site of chemical reactivity Given functional group undergoes same rxns in every molecule that it is found All compounds that have same functional group have similar properties and can be classified together

Alcohols

Alcohols organic compounds that contain one or more hydroxyl groups General formula made of functional group and R which stands for rest of compound R-OH There are rules for naming alcohols

Naming Simple Alcohols

Sample Problem

Name the organic compound shown.

1. Name the parent alkane.

Sample Problem

The chain has 4 C atoms, so the alkane is butane. Then change the e to ol:

butanol 2. Number the carbon atoms in the parent chain

Sample Problem

Number the carbon atoms in the parent chain:

Sample Problem

Remember, the hydroxyl groups should have the lowest numbers possible:

3. Insert position numbers.

Sample Problem

4. Punctuate the name.

Example, name the alcohol:

Example of a correctly named alcohol:

Given the name of the organic compount, construct the (line-bond) chemical structure:

Give me the chemical structure of:

Some common names

Ethylene glycol: 1,2-Ethanediol

Glycerol: 1,2,3-Propanetriol

General Properties of Alcohols

Boiling Point

Boiling points of alcohols usually higher than alkanes of similar molar mass

The increase in Boiling points is explained by hydrogen bonding:

Compared to alkanes extra energy needed to break H-bonds between alcohol molecules before conversion from liquid-gas

Boiling points increase as number of hydroxyl groups increase

When more than 1 OH present, molecule can form multiple H-bonds Even more energy is needed

Solubility

Remember the rule of thumb in solubility of organic compounds base on their polarity:
Like dissolves Like - Polar (hydrophilic) solutes are soluble with polar solvents, and Non-polar (hydrophobic) solutes are soluble with non-polar solvents.

Alcohols have special property, they have polar and non-polar parts.

Alcohols soluble in water b/c of H-bonding Solubility of alcohols in water usually decreases with increase in size of molecule The longer H-C chain in alcohol, the larger the nonpolar, insoluble part of molecule

Summary

Alcohols have higher boiling points than alkanes with the same MM or HC-chain Boiling point increases as number of hydroxyl group increases Solubility of alcohols to polar solvents increases as the number of hydroxyl group inreases Alcohols become insoluble to polar solvents in longer H-C chains Solubility of alcohols to non-polar solvents increases as the H-C chains becomes longer

H-bonding in alcohols also explains other properties and uses like cold creams, lipsticks, body lotions, etc.
All

include 1,2,3-propanetriol (glycerol) to keep them moist Multiple OH groups allow glycerol to form many H-bonds with water in air

Alcohols sometimes used as alternative fuels and octane enhancers, ethanol combined with gasoline in 1:9 ratio to make gasohol
Burns

more cleanly Helps save petroleum reserves Reduces dependence on oil Produces only 60% as much energy per gram as gasoline Ethanol increases water absorption in fuel

Sample Problems

Rank the following substances according to boiling point:

Butane 1-Butanol 2,3-Butanediol

Rank the following substances according to solubility with water (least soluble to most soluble):
1,2-ethanediol
Ethanol Propanol

THE END