Hydrocarbon Derivatives:

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Hydrocarbon Derivatives

• Halocarbons
• Alcohols
• Ethers

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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

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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 of molecule in specific ways
• changes depend on type functional group added

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Intermolecular Forces

• determine boiling point solubility
• van der Waals (dispersion) weakest
• nonpolar molecules
• dipole-dipole intermediate strength
• molecule has atoms with different
  electronegativities
• molecules not symmetrical
• hydrogen bonding strongest
• molecules contain H bonded to F, O, or N

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Functional Groups

• see Table R

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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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

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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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Naming Halides

• figure out backbone name
• prefixes specify halogen
• fluoro, chloro, bromo, iodo
• di, tri, tetra if more than one same halogen
• state C attached to in backbone
• gives location(s) of halogen(s)
• 0
• Note follow same basic rules learned so far
• chain so halogen has lowest
• halogen takes precedent over multiple bonds
  and branches

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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
• lowest goes to halogen alphabetically first

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Different Halogens
4 3 2
1
chlorine 1st alphabetically 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 hydrocarbon (non-polar)
• bp -162?C
• density 0.423 g/ml
• CH3Cl halogen (polar)
• bp -24?C
• density 0.911 g/ml

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Uses of Alkyl Halides

• cleaners, solvents, plastics
• examples
• Teflon PVCs
• refrigerants (used to be chlorofluorocarbons-
  now hydrofluorocarbons)

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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

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Alcohols

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

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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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alcohols are non-electrolytes!

• hydroxyl group (hydroxide ion of bases)
• - does not form ions in water! (no metal like
  bases)
• hydroxyl group is polar
• alcohols soluble in water

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Naming AlcohOLs

• based on alkane name
• name parent chain
• drop e ending replace with ol
• C OH group(s) attached to (if 3 carbons)

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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

• use prefixes di-, tri-, tetra-
• put before -ol ending
• tell of hydroxyl groups

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Classifying Alcohols

1. by of hydroxyl groups
2. by position of each hydroxyl group on main carbon
   chain

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hydroxyl groups

• monohydroxy alcohol 1 hydroxyl group
• dihydroxy alcohol 2 OH groups
• trihydroxy alcohol 3 OH groups

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position of hydroxyl group monohydroxy alcohols

• primary alcohol
• -OH group attached to end C of chain
• secondary alcohol
• -OH group attached to C bonded to 2 other Cs
• tertiary alcohol
• -OH group attached to C at branch point
  
• (C bonded to 3 other Cs)

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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

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H-bond
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Which compound has the highest boiling point?

• CH4
• C2H6
• C3H8
• C3H7OH

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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 since polar
• bent, like H2O
• ethyl ether once used as anesthesia

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Properties of Ethers

• compared to alkanes with same Cs
• higher bps than alkanes
• (ethers have greater mass due to O)
• more soluble in water than alkanes
• (ethers are polar, alkanes are not)
• compared to alcohols with same Cs
• lower bps than similar alcohols
• (ethers dont have H-bonds, alcohols do)
• much less soluble in water than alcohols
• (ethers less polar than alcohols)

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Naming Ethers

• if both hydrocarbon branches identical
• name branch only once followed by ether
• if 2 branches are different
• list names alphabetically followed by 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