Chapter 14

Organic Compounds with Oxygen and Halogens

CHEM 2124 – General Chemistry II

Alfred State College

Professor Bensley

Learning Objectives

Identify alcohols, ethers and alkyl halides. Classify alcohols and alkyl halides as 1° 2°

or 3° Determine the properties of alcohols, ethers,

and alkyl halides. Name alcohols, ehters, and alkyl halides. Draw the products of the dehydration of

alcohols. Determine the products of alcohol oxidation.

Alcohols

1o

I. Structure and PropertiesA. Classification

2o 3o

Alcohols

B. Shape and bond angle:

C. Polarity:

D. Intermolecular Forces:

Alcohols

E. Melting points and boiling points:

F. Solubility:

2 C’s in chainwater soluble

8 C’s in chainwater insoluble

Alcohols

Example

Give the IUPAC name of the following alcohol.

II. Nomenclature

• Common Names

• Diols and Triols

Alcohols

•Methanol (CH3OH)

•Ethanol (CH3CH2OH)

•2-Propanol (CH3)2CHOH), isopropyl alcohol

III. Interesting Common Alcohols

•Ethylene glycol (HOCH2CH2OH)

•Glycerol [(HOCH2)2CHOH]

Alcohols

A. Oxidation

• # of C—O bonds, # of C—H bonds

IV. Reactions of Alcohols

Alcohol Oxidation

AlcoholsB. Dehydration (Elimination Reaction) – Major Lab #2

Alcohols

C1 C2 C3 CH3H

H H H

H HOH

2-butanol

H2SO4

C1 C2 C3 CH3H

H H H

H

C1 C2 C3 CH3H

H H H

H

+ H2O

+ H2O

1-butene

2-butene

•Asymmetric alcohols can form two possible products.

• Zaitsev Rule

major product:

EthersI. Structure and Properties

A. Shape and bond angle:

B. Polarity:

C. Intermolecular Forces?

Ethers

D. Melting and Boiling Points:

E. Solubilities:

Ethers

Simple ethers are usually assigned common names:

CH3 O CH2CH3

methyl ethyl

ethyl methyl ether

CH3CH2 O CH2CH3

ethyl ethyl

diethyl ether

II. Nomenclature

More complex ethers are named using the IUPAC system:

CH3O—methoxy

CH3CH2O—ethoxy

Alkyl Halides

1o

I. Structure and Properties

2o 3o

• Polarities, Intermolecular forces, Melting and Boiling Points, Solubility

Alkyl Halides

ExampleGive the IUPAC name of the followingalkyl halide.

II. Nomenclature