1. Hydrocarbon Derivatives:
Halocarbons, Alcohols, & Ethers

2. Hydrocarbons Contain only carbon & hydrogen
carbon can also form strong covalent bonds with other elements such as:
O, N, F, Cl, Br, I, S, & P

3. Functional Group functional group:
atom or group atoms in organic molecule that always behaves the same way
Adding functional group changes chemical & physical properties in specific ways
depends on type functional group added

4. Intermolecular Forces
Determine Boiling Point & Solubility
Van der Waals or dispersion: weakest
nonpolar molecules
Dipole-dipole: intermediate strength
molecule has atoms with different electronegativities
atoms not arranged symmetrically
Hydrogen bonding: strongest
molecules contain H bonded to F, O, or N

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

7. Halocarbons/Halogens/ Organic Halides
One (or more) hydrogen atoms in alkane is replaced with halogen atom
(F, Cl, Br, or I)
No longer hydrocarbons!
called halocarbons, alkyl halides or organic halides

8. Naming Halides figure out backbone name prefixes specify substituent:
fluoro, chloro, bromo, iodo
use di, tri, tetra
if more than one same thing
tell location(s) of halogen(s)
state # C attached to 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

11. Ranking Halogens
If more than 1 kind halogen atom present – name them alphabetically
# C’s so lowest number goes to halogen alphabetically first

12. Different Halogens Chlorine 1st alphabetically: determines numbering
Chlorine 1st alphabetically: 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
alkane & alkyl halide of similar size & shape:
alkyl halide has higher bp & higher density
Why?
CH4: bp = -162C
density = g/ml
CH3Cl: bp = -24C
density = g/ml
Stronger intermolecular forces

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

16. Uses of Alkyl Halides Cleaners & solvents Examples: Teflon & PVC’s
Refrigerants (used to be chlorofluorocarbons- now hydrofluorocarbons)

17. Halogen Derivatives CH3Cl = local anesthetic (chloromethane)
CHCl3 = solvent, general anesthetic (trichloromethane)
CHI3 = antiseptic (tri-iodomethane)
CCl4 = dry cleaning solvent (tetrachloromethane)
CF2Cl2 = refrigerant (dichloro,difluoromethane)
Fluorocarbons = teflon, lubricants, synthetic blood
Chlorofluorocarbons = aerosol propellants,
refrigerants

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

21. Alcohols OH H H HCOH HCH OH group replaces H in hydrocarbon
OH group called: hydroxyl group OH H
HCOH H
HCH    

22. Alcohols are non-electrolytes!
hydroxyl group = hydroxide ion of bases
- does not form ions in water!
hydroxyl group is polar
alcohols soluble in water

23. Naming AlcohOLs Based on alkane name Name parent chain
drop –e ending & add –ol
If parent chain has 3+ C’s, # which C
OH group(s) attached to

24. 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 one OH group per C

25. More than 1 hydroxyl group
Prefixes di-, tri-, tetra-
used before -ol ending
tell # of hydroxyl groups

26. Classifying Alcohols By # of hydroxyl groups
Monohydroxy: 1 hydroxyl group
Dihydroxy: OH groups
Trihydroxy: OH groups
By position of each hydroxyl group on main carbon chain

27. Monohydroxy Alcohols
Primary: OH group attached to end C of chain or branch
Secondary: OH group attached to chain C bonded to 2 other C’s
Tertiary: OH group attached to C at branch point (C bonded to 3 other C’s)

28. 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)

29. H
H-C-H
H H
H-C-C-C-H
H O H
2-methyl 2-propanol
(Tertiary)

30. H H
H-C─C-H
O O
H H H
H-C─C─C-H
O O O
H H H
Dihydroxy
Trihydroxy

31. Properties of Alcohols
Contain: H bonded to O atom
Hydrogen Bonding
Alcohols: higher bp than corresponding alkane
‘Like dissolves Like’
Alcohols tend to be very soluble in water

32. R - O R - H O + H
H-bond +

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

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

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

38. Properties of Ethers Pure ether: no hydrogen bonding
weak dipole-dipole interactions
bent, like H2O
Ethyl ether once used as anesthesia

39. Properties of Ethers Compared to alkanes (same # C’s):
Higher bp’s than similar alkanes
More soluble in water than alkanes
Compared to alcohols (same # C’s):
Lower bp’s than similar alcohols
Much less soluble in water than alcohols

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

41. 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

42. H H H H
HCOCCCH
Methylpropyl Ether