1. Hydrocarbon Derivatives:
Halocarbons, Alcohols, & Ethers

2. Hydrocarbons Contain only carbon & hydrogen
But carbon can form strong covalent bonds to other elements, incl. O, N, F, Cl, Br, I, S, & P

3. Functional Group
One or more H’s in a hydrocarbon can be replaced by an atom or group of atoms.
An atom or group of atoms in an organic molecule that always behaves in the same way is called a functional group.
Adding a functional group changes the chemical & physical properties in specific ways, depending on the functional group.

4. Intermolecular Forces
Determine Boiling Point & Solubility
Van der Waals or dispersion – nonpolar – weakest.
Dipole-dipole – intermediate. Molecule must have atoms with different electronegativities & not arranged symmetrically.
Hydrogen bonding – strongest. Molecules must contain H bonded to F, O, or N.
Memory Jogger

5. Functional Groups Halocarbons Alcohols Ethers Amines Aldehydes Ketones
Carboxylic Acid
Ester
Amide
Amino Acid

6. Functional Group #1
Halocarbons

7. Organic Halides
One or more of the hydrogen atoms in an alkane is replaced with a halogen (F, Cl, Br, or I).
Not hydrocarbons! Often called halocarbons or alkyl halides.

8. Naming Halides Figure out the base name.
Use prefixes to specify substituent: fluoro, chloro, bromo, iodo
If more than one, use di, tri, etc. to specify # of substituents.
If necessary, give locations of halogens by numbering C-atoms in backbone.

9. CH3Cl CH3CHFCH3 H H H H–C–C–C–H H–C–Cl H F H 2-fluoropropane       
2-fluoropropane
chloromethane
C3H7F

10. Naming Halides 2,2,3-trichlorobutane CH3CCl2CHClCH3 C4H7Cl3 H Cl H H
H – C – C – C – C – H
H Cl Cl H
2,2,3-trichlorobutane
C4H7Cl3

11. Ranking Halogens
If more than 1 kind of halogen atom, list them alphabetically.
Chain is numbered to give lowest number to halogen that comes first in alphabet.

12. Different Halogens
Chlorine is 1st alphabetically, so it determines numbering.
2-chloro-4-fluoro-3-iodobutane

13. Name: Br CH3CH2CHCHCH3 I 3-bromo 2-iodo pentane F Cl HCCH
1,1-dichloro-2,2-difluoroethane

14. Properties of Halocarbons
For an alkane & an alkyl halide of similar size & shape, the alkyl halide has the higher boiling point & higher density. Why?
CH4: bp = -162C & density = g/ml
CH3Cl: bp = -24C & density = g/ml
Stronger intermolecular forces.
What intermolecular forces for CCl4?

15. Inc Inc Boiling Point (C) Density (g/ml) CH3CH2CH2CH2CH3 pentane 36
0.626
CH3CH2CH2CH2CH2F
1-fluoropentane 63
0.791
CH3CH2CH2CH2CH2Cl
1-chloropentane
108
0.882
CH3CH2CH2CH2CH2Br
1-bromopentane
130
1.218
CH3CH2CH2CH2CH2I
1-iodopentane
155
1.516
Inc
Inc

16. Uses of Alkyl Halides Cleaners & solvents
Teflon & PVC’s are alkyl halides.
Refrigerants. (used to be chlorofluorocarbons. Now hydrofluorocarbons.)
Starting materials in many reactions.

17. Halogen Derivatives CH3Cl = local anesthetic
CHCl3 = solvent, general anesthetic
CHI3 = antiseptic
CCl4 = dry cleaning solvent
CF2Cl2 = refrigerant
Fluorocarbons = teflon, lubricants, synthetic blood
Chlorofluorocarbons = aerosol propellants, refrigerants

18. Table R General Formula for halocarbons: R-X
R represents the entire hydrocarbon part of the molecule. (The alkyl part.)
X represents the halogen (F, Cl, Br, or I).

19. Functional Group #2
Alcohols

20. Alcohols -OH H H HCOH HCH
An –OH group replaces a H in a hydrocarbon.
The –OH group is called the hydroxyl group.
-OH H
HCOH H
HCH    

21. Alcohols are nonelectrolytes!
The hydroxyl group resembles the hydroxide ion of inorganic bases, but it does not form ions in water!
The hydroxyl group is polar. So alcohols are soluble in water.

22. Naming AlcohOLs Based on alkane name. Name the parent chain.
Drop the –e and add –OL.
If the parent chain has 3 or more C atoms, number the C’s & give the location of the –OH group.

23. Naming H H H H HCCCCH OH H H H H H H H HCCCCH H OH H H
1-Butanol
bp = 100C
2-Butanol
Bp = 115C
Note: Never more than 1 –OH group per C

24. More than 1 hydroxyl group
Prefixes di-, tri-, tetra- used before the –ol ending to tell the # of hydroxyl groups.
So don’t drop the -e from the alkane name.
These hydroxyls are on different C atoms!

25. Classifying Alcohols By # of hydroxyl groups
Monohydroxy: 1 hydroxyl group
Dihydroxy: 2 “ “
Trihydroxy: 3 “ “
By position of each hydroxyl group on main carbon chain.

26. Monohydroxy Alcohols
Primary: hydroxyl group attached to end C of chain or branch.
Secondary: hydroxyl group attached to C in a chain – C is bonded to 2 other C’s.
Tertiary: hydroxyl group attached to C at a branch point – C is bonded to 3 other C’s.

27. Monohydroxy H H H H H-C-C-C-C-O-H 1-butanol primary H H H H
H-C-C-C-C-H
H H O H H
2-butanol
secondary
Monohydroxy

28. H
H-C-H
H H
H-C-C-C-H
H O H
2-methyl 2-propanol
Tertiary
Monohydroxy

29. H H
H-C-C-H
O O
H H H
H-C-C-C-H
O O O
Dihydroxy
Trihydroxy

30. Properties of Alcohols
Contain a H bonded to an O atom.
Therefore Hydrogen Bonding occurs.
Alcohols have a higher boiling point than the corresponding alkane.
Like dissolves Like. Alcohols tend to be very soluble in water.

31. R - O R - H O + H +

32. Which compound has the highest boiling point?
C3H7OH
Correct response = D.

33. Table R General Formula for Alcohols: ROH.
R represents the entire hydrocarbon part of the molecule.
OH is the hydroxyl group.

34. Functional Group #3
Ethers

35. Ethers
General formula is ROR where R may or may not be the same as R.
R and R are hydrocarbon branches.
O is an oxygen bridge.
Ethers are not linear. They are bent, like water.

36. Properties of Ethers
In a pure ether, no hydrogen bonding – no H bonded to O. Do have weak dipole-dipole interactions – bent, like H2O.
Dipole-dipole interactions are between dispersion forces & hydrogen bonding.
Ethyl ether once used as anesthesia

37. Properties of Ethers Compared to alkanes: Compared to alcohols:
Higher boiling pts than similar alkanes.
More soluble in water than alkanes.
Compared to alcohols:
Lower boiling pts than similar alcohols.
Much less soluble in water than alcohols.

38. Naming Ethers
If the 2 hydrocarbon branches are identical, name the branch (once) & add the word ether.
If the 2 branches are different, list them in alphabetical order followed by the word ether.

39. H H
HCOCH
Methyl Ether
H H H H H H
HCCCOCCCH
Propyl Ether

40. H H H H
HCOCCCH
Methylpropyl Ether