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Unit 1Lesson 6 2 min read

Organic Chemistry: Functional Groups and Isomers

6/18

Learning Objectives

Define organic chemistry and identify the unique properties of carbon.
Recognize and name major functional groups, including alcohols, aldehydes, ketones, carboxylic acids, and esters.
Distinguish between different types of isomers, specifically structural isomers and stereoisomers.

The Chemistry of Carbon

Organic chemistry is the study of the structure, properties, composition, reactions, and preparation of carbon-containing compounds. Carbon is unique because:

1.It can form four stable covalent bonds.
2.It can form long chains and rings, both single, double, and triple bonds.

This allows for an immense diversity of molecules.

Functional Groups

A functional group is a specific group of atoms or bonds within a molecule that is responsible for the characteristic chemical reactions of that molecule. The rest of the molecule is often referred to as 'R'.

Key Functional Groups:

Alcohol (-OH): Contains a hydroxyl group. (e.g., ethanol, R-OH).
Aldehyde (-CHO): Contains a carbonyl group (C=O) at the end of a carbon chain. (e.g., propanal, R-CHO).
Ketone (-CO-): Contains a carbonyl group (C=O) in the middle of a carbon chain. (e.g., acetone, R-CO-R').
Carboxylic Acid (-COOH): Contains a carboxyl group, which is a carbonyl and a hydroxyl on the same carbon. They are acidic. (e.g., acetic acid, R-COOH).
Ester (-COO-): Similar to a carboxylic acid, but the hydroxyl hydrogen is replaced by another carbon group. They often have fruity smells. (e.g., ethyl acetate, R-COO-R').
Amine (-NH₂): Contains a nitrogen atom bonded to carbon. They are basic. (R-NH₂).
Ether (-O-): An oxygen atom bonded to two carbon groups. (R-O-R').

Isomers: Same Formula, Different Structure

Isomers are molecules that have the same molecular formula but a different arrangement of atoms.

1. Structural (or Constitutional) Isomers:

Atoms are connected in a different order.
They have different physical and chemical properties.
Example: Butane and Isobutane both have the formula C₄H₁₀. Butane is a straight chain, while isobutane is branched.

2. Stereoisomers:

Atoms are connected in the same order, but have a different spatial arrangement.
Geometric Isomers (cis-trans): Occur due to restricted rotation, usually around a double bond.
cis isomer: The two higher-priority groups are on the same side of the double bond.
trans isomer: The two higher-priority groups are on opposite sides.
Enantiomers (Optical Isomers): Molecules that are non-superimposable mirror images of each other, like a left and right hand. They occur in molecules with a chiral center (a carbon atom bonded to four different groups).

Key Terms

Isomers
Molecules that have the same molecular formula but a different arrangement of atoms in space.
Functional Group
A specific group of atoms within a molecule that is responsible for the characteristic chemical reactions of that molecule.
Structural Isomers
Isomers that differ in the covalent arrangements of their atoms (i.e., the connectivity is different).
Stereoisomers
Isomers that have the same molecular formula and sequence of bonded atoms (constitution), but differ in the three-dimensional orientations of their atoms in space.
Enantiomers
A pair of molecules that are non-superimposable mirror images of each other.

Check Your Understanding

1

Name the functional group present in CH₃COOH and classify it as acidic or basic.

2

What is the key structural requirement for a molecule to have enantiomers (optical isomers)?

3

Draw and name two structural isomers with the molecular formula C₃H₈O.