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. C 6 H 12 + 9 O 2 6 CO 2 + 6 H 2 O Write the equation for the complete combustion of ethylbutanoate. O C 6 H 12 O 2 + 8 O 2 6 CO 2 + 6 H 2 O O
substitution: an H atom is removed and “something else” is put in its place halogen atom replaces an H. -- In halogenation, a _______ Write an equation for the reaction between ethane and chlorine. H H H –C–C–H + Cl 2 H–C–C–Cl + HCl H H If more chlorine is provided, the reaction will produce. . . H H H –C–C–Cl + Cl 2 Cl–C–C–Cl + HCl H H AND SO ON.
Substitution occurs with aromatic compounds, too. Br + Br 2 + CH 3 CH 2 Cl catalyst + 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.
addition: a multiple bond is broken and two “things” are inserted (p(s) is/are broken, s remains intact) H H Br–C–C–Br + Br 2 C=C H H H H H–C–C–Br + HBr C=C H H H H H 2 SO 4 H–C–C–OH + H 2 O C=C H H H H Cl H H–C–C–H + Cl 2 H –C–C=C–C– H H Cl H H H
A specific addition rxn is hydrogenation, in which __ H is added across a multiple C-C bond. -- requires a catalyst (usually a finely-divided _____) metal to rupture the multiple bond H H C=C H H + H 2 catalyst H H H–C–C–H H H Another addition reaction is polymerization. H H H C=C H H –C–C– C=C H HH H H C=C H H “lots” of ethylene polyethylene
condensation (or elimination, or dehydration): water is a product _____ -- One reactant provides an __, H the other provides an ___. OH Complex protein molecules are made from condensation reactions of amino acids. NO 2 + HNO 3 H 2 SO 4 CH 3 CH 2 OH + CH 3 OH alcohol m’c + H 2 O CH 3 CH 2–O–CH 3 + H 2 O an ether water
-- Condensation reactions polymerize amino acids into. . . proteins. R” O H–N–C–C–OH H H amino acid #1 R’ O Note that amino + H–N–C–C–OH acids have amine groups attached H H to the C NEXT TO amino acid #2 the carboxyl group. R” O R’ O H–N–C–C–OH H H “a bit of a” protein + H 2 O water
-- Amides can be formed in condensation rxns between carboxylic acids and amines. Write the equation for the reaction between butanoic acid and ammonia. Ammonia is the simplest amine. O O + NH 3 + H 2 O OH carboxylic acid amine NH 2 amide water
Esterification is a condensation reaction between a carboxylic acid an alcohol. Write the equation for the reaction between butanoic acid and 1 -butanol. O + OH HO O O butylbutanoate + H 2 O (the active substance in the characteristic flavor/odor of pineapple)
Write the equation for the reaction between 3 -phenyl-2 -propenoic acid and ethanol. O + HO OH O + H 2 O (the active substance in O ethyl-3 -phenyl-2 -propenoate (i. e, ethyl cinnamate ) the characteristic flavor/odor of cinnamon) “When in doubt, make water. ” Mr. B