Upload
grant-lynch
View
259
Download
3
Tags:
Embed Size (px)
Citation preview
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
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
Intermolecular Forces
• Determine Boiling Point & Solubility• Van der Waals or dispersion: weakest
– nonpolar molecules
• Dipole-dipole: intermediate strength– molecule has atoms with different
electronegativities– atomsatoms not not arranged symmetrically
• Hydrogen bonding: strongest – molecules contain H bonded to F, O, or N
Functional Groups
1.Halocarbons
2.Alcohols
3.Ether
4.Aldehydes
5.Ketones
6.Carboxylic Acid
7.Ester
8.Amines9.Amide
10.Amino Acid
Halocarbons/Halogens/Organic Halides
• One (or more) hydrogen atoms in alkane is replaced with halogen atom
(F, Cl, Br, or I)
• No longerNo longer hydrocarbons! • called halocarbons, alkyl halides or organic
halides
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
Naming Halides
CH3CCl2CHClCH3 C4H7Cl3
H Cl Cl H H
H – C C – – C C – – C C – – CC – H H Cl ClCl Cl H
2,2,3-trichlorotrichlorobutanebutane
Ranking Halogens
• If more than 1 kind halogen atom present – name them alphabetically
• # C’s so lowest number goes to halogen alphabetically first
Different Halogens
Chlorine 1st alphabetically: determines numbering
4 3 2 1
2-chloro-4-fluoro-3-iodobutane
Properties of Halocarbons
• alkane & alkyl halide of similar size & shape:– alkyl halide has higher bp & higher density
Why?
• CH4: bp = -162C
density = 0.423 g/ml
• CH3Cl: bp = -24C
density = 0.911 g/ml
Stronger intermolecular forcesStronger intermolecular forces
1.516155CH3CH2CH2CH2CH2I
1-iodopentane
1.218130CH3CH2CH2CH2CH2Br
1-bromopentane
0.882108CH3CH2CH2CH2CH2Cl
1-chloropentane
0.79163CH3CH2CH2CH2CH2F
1-fluoropentane
0.62636CH3CH2CH2CH2CH3
pentane
Density
(g/ml)
Boiling Point
(C)
Inc Inc
Uses of Alkyl Halides
• Cleaners & solvents
• Examples: – Teflon & PVC’s – Refrigerants (used to be chlorofluorocarbons-
now hydrofluorocarbons)
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
Table R
• General Formula halocarbons: R-X
– R represents entire hydrocarbon part of molecule
– X represents halogen (F, Cl, Br, or I)
Alcohols
• OH group replaces H in hydrocarbon
• OH group called: hydroxyl group
HHCH H
OHOH HHCOHOH H
Alcohols are non-non-electrolytes!
• hydroxyl group = hydroxide ion of bases - does not form ions in water!
• hydroxyl group is polar – alcohols soluble in water
Naming AlcohOLOLs
• Based on alkane name
• Name parent chain– drop –e ending & add –olol
• If parent chain has 3+ C’s, # which C
OH group(s) attached to
Naming
H H H HHCCCCH OH H H H
1-Butanolbp = 100C
H H H HHCCCCH H OH H H
2-ButanolBp = 115C
Note: Never more than one OH group per C
More than 1 hydroxyl group
• Prefixes di-, tri-, tetra- – used before -ol ending – tell # of hydroxyl groups
Classifying Alcohols
• By # of hydroxyl groups
–Monohydroxy: 1 hydroxyl group
–Dihydroxy: 2 OH groups
–Trihydroxy: 3 OH groups
• By position of each hydroxyl group on main carbon chain
Monohydroxy Alcohols
• PrimaryPrimary: OH group attached to end C of chain or branch
• SecondarySecondary: OH group attached to chain C bonded to 2 other C’s
• TertiaryTertiary: OH group attached to C at branch point (C bonded to 3 other C’s)
Properties of Alcohols
• Contain: H bonded to O atom
– Hydrogen Bonding Hydrogen Bonding
• Alcohols: higher bphigher bp than corresponding alkane
• ‘‘Like dissolves LikeLike dissolves Like’’ – Alcohols tend to be very soluble in water
Table R
• General Formula Alcohols: ROH• R represents entire hydrocarbon part of
molecule
• OH is hydroxyl group
Ethers
• General formula ROR – 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
Properties of Ethers
• PurePure ether: no hydrogen bonding – weak dipole-dipole interactions
– bent, like H2O
• Ethyl ether once used as anesthesia
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
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