1. Organic Reactions combustion of hydrocarbons OR compounds w /only C, H, and O: products are… CO 2 and H 2 O Write the equation for the complete combustion of 2-methyl-2-pentene. Write the equation for the complete combustion of ethylbutanoate.  C 6 H 12 + O 2 CO 2 + H 2 O 669 O O  C 6 H 12 O 2 + O 2 CO 2 + H 2 O 668

2. substitution: an H atom is removed and “something else” is put in its place -- In halogenation, a _______ atom replaces an H. halogen Write an equation for the reaction between ethane and chlorine. + Cl 2  –C–C–H HH H HH –C–C–Cl HH H HH + HCl If more chlorine is provided, the reaction will produce... AND SO ON. –C–C–Cl HH H HH + Cl 2  –C–C–Cl HH Cl HH + HCl

3. Substitution occurs with aromatic compounds, too. + Br 2 catalyst + CH 3 CH 2 Cl catalyst Br + HBr+ HCl Ethylbenzene is an important intermediate in the production of styrene which, in turn, is used to make polystyrene. Roughly 25 million tons of ethylbenzene are produced and used every year.

4. addition: a multiple bond is broken and two “things” are inserted (  (s) is/are broken,  remains intact) –C–C–Br HH Br HH –C–C–Br HH H HH –C–C–OH HH H HH + Br 2 H C=C H HH + HBr H C=C H HH + H 2 O H C=C H HH H 2 SO 4 H–C–C–C–C–H H H H H + Cl 2 –C–C=C–C– ClHH HH HH

5. A specific addition rxn is hydrogenation, in which __ is added across a multiple C-C bond. H -- requires a catalyst (usually a finely-divided _____) to rupture the multiple bond metal –C–C–H HH H HH + H 2 H C=C H HH catalyst Another addition reaction is polymerization. “lots” of ethylene H C=C H HH H H HH H H HH polyethylene –C–C–C–C– HH HH HH HH

6. condensation (or elimination, or dehydration): _____ is a product water -- One reactant provides an __, the other provides an ___. H OH CH 3 CH 2 OH + CH 3 OH NO 2 + H 2 O + HNO 3 H 2 SO 4 CH 3 CH 2 –O–CH 3 + H 2 O wateralcohol m’c an ether Complex protein molecules are made from condensation reactions of amino acids.

7. -- Condensation reactions polymerize amino acids into... proteins. H–N–C–C–OH OR” HH amino acid #1 H–N–C–C–OH OR’ HH amino acid #2 + H–N–C–C– OR” HH N–C–C–OH OR’ HH “a bit of a” protein + H 2 O water Note that amino acids have amine groups attached to the C NEXT TO the carboxyl group.

8. -- Amides can be formed in condensation rxns between carboxylic acids and amines. Write the equation for the reaction between butanoic acid and ammonia. O OH + NH 3 O NH 2 + H 2 O carboxylic acidamineamidewater Ammonia is the simplest amine.

9. Esterification is a condensation reaction between a carboxylic acid and an alcohol. Write the equation for the reaction between butanoic acid and 1-butanol. O OH HO + O O + H 2 O butanoate butyl (the active substance in the characteristic flavor/odor of pineapple)

10. Write the equation for the reaction between 3-phenyl-2-propenoic acid and ethanol. O OH HO + H2OH2O + -3-phenyl-2-propenoate (the active substance in the characteristic flavor/odor of cinnamon) ethyl (i.e, ethyl cinnamate ) “When in doubt, make water.” Mr. B O O