1. FUNCTIONAL GROUPS

2. ORGANIC HALIDES Properties
Halogen makes the molecule more polar, increasing strength of the intermolecular forces
Higher boiling points than their corresponding hydrocarbons
More soluble in polar solvents
Molecules with more halogens are more polar

3. Preparing Organic Halides
Recall: Substitution reaction produce halides in alkanes and aromatic hydrocarbons

4. Preparing Organic Halides
Recall: alkyl halides are produced in halogenation reactions (addition) with alkenes/alkynes

5. Elimination Reactions
Preparing alkenes from alkyl halides
Most common method of preparing alkenes
Alkyl halides can eliminate a hydrogen and a halide ion from adjacent carbon atoms forming a double bond.
Presence of a hydroxide ion is required

6. ALCOHOLS Organic compounds containing a hydroxyl group -OH
E.g. ethanol, cholesterol, retinol (vitamin A)
Naming:
-ol suffix e.g. methane + OH = methanol

7. Polyalcohols Alcohols containing more than one -OH group
-diol, -triol suffix
Or hydroxy prefix
1,2-dihydroxyethane
1,2,3-trihydroxypropane

8. Properties of Alcohols
More polar and can hydrogen bond
Higher boiling points
More soluble in polar solvents
Long-chain alcohols are nonpolar (hydrocarbon portion) and polar (-OH)
Ideal solvents in organic reactions because they will dissolve both polar and nonpolar compounds

9. Hydration Reactions (Addition) (Formation of Alcohol)
REACTIONS INVOLVING ALCOHOLS
Hydration Reactions (Addition) (Formation of Alcohol)
Alkene + water --> alcohol
Follows Markovnikov’s rule
Combustion of Alcohols

10. Elimination Reactions
Dehydration (Condensation) Reactions:
Under certain conditions alcohols can decompose to produce alkenes and water
A catalyst (sulfuric acid) removes a hydrogen atom and a hydroxyl group from neighbouring carbons
Resulting in C=C and H2O

11. ETHERS Molecules with C-O-C group More polar than hydrocarbons
But, unlike alcohols, ethers cannot hydrogen bond
Naming:
Add oxy to the prefix of the smaller hydrocarbon group and join it to the alkane name of the larger hydrocarbon group
E.g. CH3-O-C2H5 is methoxyethane

12. Condensation Reactions (Formation of Ethers)
When two alcohols combine, an ether and water are formed

13. ALDEHYDES AND KETONES
Ketone: Molecule with a carbonyl group (C=O) between two carbon atoms. Alkane name with -one suffix
Aldehyde: Molecule with a carbonyl group (C=O) on a terminal carbon. Alkane name with -al suffix

14. Properties of Aldehydes and Ketones
Polar but no Hydrogen Bonding
Lower boiling point and less soluble in water than alcohols (no -OH)
More polar than hydrocarbons (higher boiling points and more soluble)
Good solvents (both polar and nonpolar)

15. Oxidation Reactions
Alcohol + an oxidizing agent (removes electrons) to form an aldehyde or ketone and water
The oxidizing agent removes two H-atoms (one from the -OH group and one from the adjacent carbon) resulting in C=O and H2O

16. Oxidizing agent
No available H-atom

18. Hydrogenation Reactions
The C=O double bond can undergo an addition reaction with hydrogen to form an -OH group.
Aldehydes always produce 1˚ alcohols
Ketones always produce 2˚ alcohols

19. CARBOXYLIC ACIDS Molecules with a carboxyl group -COOH
E.g. lactic acid, citric acid
NAMING:
Alkane name with -oic acid
E.g. methanoic acid

20. Properties of Carboxylic Acids
Polar
Can hydrogen bond
Similar properties to alcohols (smaller members are soluble in water, larger members are insoluble)
pH < 7 (H-atom in -OH group)

21. Oxidation Reactions
Recall: A 1˚ alcohol can be oxidized to form an aldehyde.
An aldehyde can be further oxidized to form a carboxylic acid
A ketone cannot be oxidized because there is no free H-atom

22. Oxidation Reaction

23. ESTERS NAMING: 1st name is the part single bonded to only 1 Oxygen
(the part that was originally the alcohol)  it gets named like a side chain with the ending ‘-yl’
2nd name is the part double bonded to the Oxygen  it is named with the ending ‘-oate’

24. EXAMPLES

25. Esterfication (Formation of Esters)
Recall: acid + base --> salt + water (neutralization reaction)
Carboxylic acid alcohol --> ester water
Properties of Esters
Similar to carboxylic acids, but lacking -OH group
Esters are less polar (less soluble in water), lower boiling points (no H-bonds)
Not acidic
Many have characteristic scents

26. AMINES
An ammonia molecule in which one or more H-atoms are substituted by alkyl or aromatic groups
Naming:
Amino + alkane name OR
Alkyl group + amine

27. Naming 2˚ and 3˚ Amines
N- prefix used for the substituted groups on the nitrogen atom
Alkyl groups are listed alphabetically
N,N-dimethyl-2-aminopropane

28. Properties of Amines N-C, and N-H polar bonds
H-bonding occurs but N-H is less polar than O-H

29. Synthesizing Amines from Alkyl Halides
Alkyl halide + ammonia --> 1˚ amine + HX
Alkyl halide + 1˚ amine --> 2˚ amine + HX
Alkyl halide + 2˚ amine --> 3˚ amine + HX

30. Synthesizing Amines from Alkyl Halides

31. AMIDES Similar to esters, except N instead of O
Recall: Carboxylic acids + alcohols --> esters + water
Carboxylic acids + ammonia/1˚/2˚ amines--> amides + water

32. Naming Amides 1st part is the name is from the amine
2nd part is the ending of the acid name changed from -oic to -amide
Alphabetical order with N- groups
N-ethyl propanamide

33. Summary