Ch 11 carbon a multifarious element
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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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Ch 11 carbon a multifarious element l.jpg

Ch. 11: Carbon A Multifarious Element


Why carbon l.jpg
Why Carbon?

  • Versatility

  • Single, double, triple bonds

  • Structural diversity


Short hand for expressing carbon based compounds l.jpg
Short-hand for expressing carbon-based compounds

  • C4H10: butane

  • Structural formula

  • Condensed structural formula

  • Carbon skeleton formula

  • C4H8

  • C4H6


Isomers l.jpg
Isomers

  • Isomers – same composition, diff. structures

  • Structural isomers: same # atoms, diff. structures

    Ethanol (C2H6O) vs. dimethylether (C2H6O)


Problems l.jpg
Problems

  • Draw all isomers of C3H8O. There are 3.

  • Draw all isomers of C4H8Br2. There are 9.


Stereoisomers l.jpg
Stereoisomers

  • Same formula, diff. orientation

  • Two types:

  • 1) geometric

  • 2) optical isomers


Geometric isomers l.jpg
Geometric isomers

  • Require double bond!

  • Cis vs. trans


Optical isomers l.jpg
Optical isomers

  • Nonsuperimposable mirror images

  • Called chiral molecules (chirality)

  • Pairs of chiral molecules = enantiomers


Classes of carbon containing cmpds l.jpg
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 l.jpg
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 l.jpg
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 l.jpg
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 l.jpg
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 l.jpg
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 l.jpg
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 l.jpg
Naming Halohydrocarbons structures and name them

  • 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 l.jpg
Naming Aromatic Cmpds structures and name them

  • Monosubstitution:

    • Methylbenzene  toluene

    • Phenol

    • Aniline

  • Disubstitution:

  • o- = ortho

  • m- = meta

  • p- = para


Practice l.jpg
Practice structures and name them

  • 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 l.jpg
Other functional groups structures and name them

  • 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 l.jpg
Practice: rename if necessary structures and name them

  • 1-propanol

  • 2-propanol

  • 3-propanol

  • Now, I’ll draw some and you name them


Other functional groups21 l.jpg
Other functional groups structures and name them

  • 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 l.jpg
Practice structures and name them

  • Dimethylether

  • Butoxyhexane

  • methoxyethane

  • Now, I’ll draw some and you name them


Other functional groups23 l.jpg
Other functional groups structures and name them

  • Amines

  • RNH2

  • Putrescine = 1,4-butanediamine

  • Cadaverine = 1,5-pentanediamine


Practice24 l.jpg
Practice structures and name them

  • Triethylamine

  • Triisopropylamine

  • Now, I’ll draw some and you name them


Other functional groups25 l.jpg
Other functional groups structures and name them

  • 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 l.jpg
Practice structures and name them

  • Methanal

  • Hexanal

  • 2-pentanone

  • 4-decanone

  • Now, I’ll draw some and you name them


Other functional groups27 l.jpg
Other functional groups structures and name them

  • 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 l.jpg
Practice structures and name them

  • 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 l.jpg
Other functional groups structures and name them

  • Amides

  • RCONR2

  • Ex: methanamide, ethanamide


Polymers l.jpg
Polymers structures and name them

  • 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


Styrofoam teflon silicone kevlar l.jpg
Styrofoam, Teflon, silicone, Kevlar structures and name them


Condensation polymers l.jpg
Condensation Polymers structures and name them

  • Combining monomers and splitting out small molecules (like water)

    • Demo

      • Making nylon

  • Demo

    • Green “snot”


Green snot l.jpg
Green “snot” structures and name them


Copolymers l.jpg
Copolymers structures and name them

  • 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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