Organic Chemistry Chapter 2

Organic Functional Groups

R – WHAT???

R – OH

C – OHC – C – OH C – C – C – C – OH

Ohh, I get it – They are all alcohols???

Naming Strait Chains

Substituents

Halogen Substituents - F(Floro) Cl (Chloro) Br (Bromo) I (Iodo)

Naming Rules

1. Find the longest carbon chain

2. Circle the longest chain

3. Number the chain starting at the end with closest substituent

4. Name the substituents

5. Name the longest chain

Naming Tips

• When two or more substituents are on the same carbon, use the number twice.

• When two or more substituents are identical, use prefixes

• When two chains are the same length, use the one with the most substituents on it.

• If substituents are at equall distances from the ends of the chain, go to the next substituent.

• Iso and cyclo are included alphabetically, di, tri, tetra, sec, tert are not

Using Common Names

The alkyl group followed by the name

of the functional groupCH3CH2CH2CH2CH2OH – pentyl alcohol

CH3CH2CH2OH – propylalcohol

Notice no space in propyl

CH3CH2CH2CH2NH2 – butyl amine

Degree Designation

Naming Cyclics• Add the prefix cyclo to the name of the

number of carbons• If there are substituents, name them

first with numbers producing the lowest value

• If the carbon chain has more carbons than the cyclic, name it as a substituent

Br1

2

3

4

5

1-bromo-3-ethylcyclopentane

12

34 5 6

7

3-cyclopropylheptane

Naming Ethers

• Name the two alkyl substituents in alphabetical order and then add either.

• If identical use di, tri,…..

• IUPAC – replace yl ending with oxy

OO

butyl hexyl ether

1-butoxy-2,3-dimethylpentane

Degree of alcohol

Naming Alcohols

• Longest chain should include the OH group• Number chain giving the alcohol the lower number• To name, replace e to ol

OH

Br

Br

12

34

5

76

5,6-dibromo-3-heptanol

Br

OH1

2

34

5

7

6

3-bromocycloheptanol

OH

12

34

5 76 8

9

3-propyl-2-nonanol

Degree of Amine

Naming Amines

• List the name of each alkyl group attached to the nitrogen and then add amine

• Name is written as one word• For four groups attached to a nitrogen, use

alkyl groups and then ammonium• IUPAC – replace the e with amine• N – designates the alkyl group is attached to

the N and not a C

Naming Amines

Naming Amines

Structure of Alkyl Halides, Alcohols, Ethers and Amines

• Read through pages 92-93 in book

Boiling Points

• The larger the molecular weight the greater the boiling point

• The greater the number of branches the lower the boiling point

• The greater number of electronegative atoms the higher the boiling point

Intermolecular Forces

Hydrogen bondAttraction between molecules that have a Hydrogen connected to a F, O or NVery strong attractive force – breaks pipes in the winterResponsible for Surface Tension

Dipole Force – Attraction due to different electronegativities

Disperson, london, or van der Waals forceProduced from temporary dipoles

Read through section in book and be familiar

Surface Tension

Melting Points

• Melting points follow the same rules as boiling points with the addition of crystal packing.

• This makes them less predictable

Solubility

• The rough rule for organic solubility is that it takes one polar group for each 4 carbons to get it to dissolve in water

Rotation in Ethane

Rotation in Butane

Cyclohexane

Cis and Trans

Axial / Equatorial