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Ch. 11: Carbon A Multifarious Element. Why Carbon?. Versatility Single, double, triple bonds Structural diversity. Short-hand for expressing carbon-based compounds. C 4 H 10 : butane Structural formula Condensed structural formula Carbon skeleton formula C 4 H 8 C 4 H 6. Isomers.

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why carbon
Why Carbon?
  • Versatility
  • Single, double, triple bonds
  • Structural diversity
short hand for expressing carbon based compounds
Short-hand for expressing carbon-based compounds
  • C4H10: butane
  • Structural formula
  • Condensed structural formula
  • Carbon skeleton formula
  • C4H8
  • C4H6
isomers
Isomers
  • Isomers – same composition, diff. structures
  • Structural isomers: same # atoms, diff. structures

Ethanol (C2H6O) vs. dimethylether (C2H6O)

problems
Problems
  • Draw all isomers of C3H8O. There are 3.
  • Draw all isomers of C4H8Br2. There are 9.
stereoisomers
Stereoisomers
  • Same formula, diff. orientation
  • Two types:
  • 1) geometric
  • 2) optical isomers
geometric isomers
Geometric isomers
  • Require double bond!
  • Cis vs. trans
optical isomers
Optical isomers
  • Nonsuperimposable mirror images
  • Called chiral molecules (chirality)
  • Pairs of chiral molecules = enantiomers
classes of carbon containing cmpds
Classes of Carbon-Containing Cmpds
  • Hydrocarbons
  • Only C & H
  • Alkane: CnH2n+2
  • (Saturated every C-C bond single)
  • Alkene: CnH2n (at least one double bond btwn C’s)
  • (Unsaturated  double, triple bonds)
classes of carbon containing cmpds10
Classes of Carbon-Containing Cmpds
  • Alkyne: CnH2n-2 (at least one triple bond btwn C’s)
  • Cyclohydrocarbons: rings of carbon
  • Aromatic: rings w/pi-bonding
    • benzene
naming alkanes
Naming Alkanes
  • Suffix: -ane
  • Count out longest carbon chain
  • Prefixes:
  • 1C meth-
  • 2C eth-
  • 3C prop-
  • 4C but-
  • 5C pent-
  • 6C hex-
  • 7C hept-
  • 8C oct-
  • 9C non-
  • 10C dec-
naming alkanes12
Naming Alkanes
  • Hydrocarbon substitution = alkyl groups
  • Meth  methyl, etc.
  • Use number, followed by “-”, to designate placement of substituent
    • 2-methylpentane
  • If 2 or more of same subs.  di, tri, tetra, etc.
    • 2,3-dimethylpentane
  • If more than one different alkyl group, use alphabetic ordering
    • Butyl precede ethyl precedes methyl
      • 4-ethyl-3-methylheptane
  • In naming hydrocarbons always go with longest carbon-chain
draw out the following alkanes and rename them if needed
Draw out the following alkanes and rename them, if needed
  • Hexane
  • 2-methylhexane
  • 2,2-diethylpropane
  • 4-ethyl-2-methylnonane
  • Now, I’ll draw some and you name them
naming alkenes alkynes
Naming Alkenes, alkynes
  • Start counting carbon chain from lowest carbon containing double/triple bond
  • 1-propene, not 2-propene
  • Use number, followed by “-”, to designate placement of double or triple bond
    • 1-butene
    • 2-octyne
draw the following and if there is isomerism draw both structures and name them
Draw the following and if there is isomerism draw both structures and name them
  • 1-hexene
  • 2-hexene
  • 3-heptyne
  • 2-methyl-3-heptyne
  • Now, I’ll draw some and you name them
naming halohydrocarbons
Naming Halohydrocarbons
  • Same rules apply
    • In alphabetical order
    • Bromine  bromo
    • chlorine  chloro
    • fluorine  fluoro
    • iodine  iodo
  • Ex: 2-chlorobutane
  • Practice (fix if necessary):
  • 3-bromo-2-chloropentane
  • 3,3-diiodobutane
  • Now, I’ll draw some and you name them
naming aromatic cmpds
Naming Aromatic Cmpds
  • Monosubstitution:
    • Methylbenzene  toluene
    • Phenol
    • Aniline
  • Disubstitution:
  • o- = ortho
  • m- = meta
  • p- = para
practice
Practice
  • Chlorobenzene (does it make a difference where you put the Cl?)
  • Draw all isomers (and name them) of a benzene that has 1 bromine and one fluorine
    • Which combinations are disallowed and why?
other functional groups
Other functional groups
  • Functional group = characteristic grouping or arrangement of atoms
  • Alcohols = R-OH
  • Methanol, ethanol, propanol, etc.
  • Structural isomers of alcohols
  • 1,2-ethanediol = ethylene glycol
practice rename if necessary
Practice: rename if necessary
  • 1-propanol
  • 2-propanol
  • 3-propanol
  • Now, I’ll draw some and you name them
other functional groups21
Other functional groups
  • Ether: ROR’

1) Select the longest carbon chain and name it as the correct alkane.

2) Change the “-yl” ending of the other (shorter) hydrocarbon group to “-oxy” to

obtain the alkoxy group name.

3) Combine the two names giving the alkoxy group name first.

practice22
Practice
  • Dimethylether
  • Butoxyhexane
  • methoxyethane
  • Now, I’ll draw some and you name them
other functional groups23
Other functional groups
  • Amines
  • RNH2
  • Putrescine = 1,4-butanediamine
  • Cadaverine = 1,5-pentanediamine
practice24
Practice
  • Triethylamine
  • Triisopropylamine
  • Now, I’ll draw some and you name them
other functional groups25
Other functional groups
  • Aldehydes
  • RCOH
  • Start counting the carbon-chain from the C=O
  • Methanal, butanal, hexanal
  • Ketones
  • RCOR’
  • Start counting the carbon-chain from the C=O
  • 2-propanone, 3-heptanone
practice26
Practice
  • Methanal
  • Hexanal
  • 2-pentanone
  • 4-decanone
  • Now, I’ll draw some and you name them
other functional groups27
Other functional groups
  • Carboxylic acids
  • RCOOH
  • Start counting the carbon-chain from the C=O
  • Methanoic acid, ethanoic acid, etc.
  • Esters
  • RCOOR’
  • Start counting the carbon-chain from the C=O
  • -OR’  takes on alkyl name
  • RCO  takes on –oate suffix
  • Thus, HCOOCH3 methyl methanoate
  • By the way, acetate = ethanoate
practice28
Practice
  • Hexanoic acid
  • 2-methylpropanoic acid (give its other name)
  • Hexyl ethanoate
  • Butyl butanoate
  • 3-methylbutyl ethanoate (has a more common name)
  • Now, I’ll draw some and you name them
other functional groups29
Other functional groups
  • Amides
  • RCONR2
  • Ex: methanamide, ethanamide
polymers
Polymers
  • Huge molecules with repeating monomers (subunits)
  • Thermoplastics (polyethylene, styrofoam): respond to heating
  • Soften and flow when heated, harden when cooled; reversible
    • Over 60 million tons of polyethylene produced annually!
  • Thermosetting plastics (Formica-brand): initially soft, but solid when heated; irreversible
condensation polymers
Condensation Polymers
  • Combining monomers and splitting out small molecules (like water)
    • Demo
      • Making nylon
  • Demo
    • Green “snot”
copolymers
Copolymers
  • Polymerization of 2 (or more) diff. monomers
  • Such as:
    • Styrene-butadiene rubber (SBR)
      • Predominately used for car and light-truck tires
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