Hydrocarbon Derivatives:

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Hydrocarbon Derivatives

• Halocarbons, Alcohols, Ethers

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Hydrocarbons

• Contain only carbon hydrogen
• But carbon can also form strong covalent bonds
  with other elements such as
• O, N, F, Cl, Br, I, S, P

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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

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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

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Functional Groups

1. Halocarbons
2. Alcohols
3. Ether
4. Aldehydes
5. Ketones
6. Carboxylic Acid
7. Ester
8. Amines
9. Amide
10. Amino Acid

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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

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Naming Halides

• Figure out backbone name
• prefixes specify substituent
• fluoro, chloro, bromo, iodo
• use di, tri, tetra (if more than one same thing)
• Give location(s) of halogen(s)
• tell C attached to in backbone

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• CH3Cl CH3CHFCH3

H H H HCCCH H F H
H HCCl H
2-fluoropropane
chloromethane
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Ranking Halogens

• If more than 1 kind halogen atom present name
  them alphabetically
• Cs so lowest number goes to halogen
  alphabetically first

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Different Halogens
4 3 2
1
Chlorine is 1st alphabetically, so it determines
numbering
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Name
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Properties of Halocarbons

• alkane alkyl halide of similar size shape
• alkyl halide has higher bp higher density
• Why?
• CH4 bp -162?C
• density 0.423 g/ml
• CH3Cl bp -24?C
• density 0.911 g/ml

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Uses of Alkyl Halides

• Cleaners solvents
• Examples
• Teflon PVCs
• Refrigerants (used to be chlorofluorocarbons-
  now hydrofluorocarbons)

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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

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Table R

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

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Alcohols

• OH group replaces H in hydrocarbon
• OH group called hydroxyl group

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Alcohols are nonelectrolytes!

• hydroxyl group hydroxide ion of inorganic bases
  
• - does not form ions in water!
• The hydroxyl group is polar
• alcohols soluble in water

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Naming AlcohOLs

• Based on alkane name
• Name parent chain
• Drop the e and add ol
• If parent chain has 3 Cs, which C
• OH group(s) attached to

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Naming
H H H H H?C?C?C?C?H H OH H H
1-Butanol bp 100?C
2-Butanol Bp 115?C
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More than 1 hydroxyl group

• Prefixes di-, tri-, tetra- used before ol ending
  tell of hydroxyl groups

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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

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Monohydroxy Alcohols

• Primary hydroxyl group attached to end C of
  chain or branch
• Secondary hydroxyl group attached to C in chain
  bonded to 2 other Cs
• Tertiary hydroxyl group attached to C at a
  branch point (C bonded to 3 other Cs)

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Properties of Alcohols

• Contain H bonded to O atom
• Hydrogen Bonding
• Alcohols have higher bp than corresponding
  alkane
• Like dissolves Like
• Alcohols tend to be very soluble in water

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Which compound has the highest boiling point?

• CH4
• C2H6
• C3H8
• C3H7OH

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Table R

• General Formula Alcohols R?OH
• R represents entire hydrocarbon part of molecule
• OH is hydroxyl group

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Ethers

• General formula R?O?R?
• 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

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Properties of Ethers

• Pure ether no hydrogen bonding
• weak dipole-dipole interactions
• bent, like H2O
• Ethyl ether once used as anesthesia

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Properties of Ethers

• Compared to alkanes (same Cs)
• Higher bps than similar alkanes
• More soluble in water than alkanes
• Compared to alcohols (same Cs)
• Lower bps than similar alcohols
• Much less soluble in water than alcohols

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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

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H H H?C?O?C?H H H
H H H H H H H?C?C?C?O?C?C?C?H
H H H H H H
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H H H H H?C?O?C?C?C?H H H
H H