3. 4. Hydrolysis of alkyl halides (CH3 or 1o) 5. 6. 7. 8. R-H R-X R-OH Acids NR NR Bases NR some
Active metals NR Oxidation NR NR 1o/2o Reduction NR NR Halogens
NR NR NR Alcohols, reactions: R-|-OH 1. With HX 2. With PX3 3. (later) RO-|-H 4. As acids 5. Ester formation 6. Oxidation 1. Reaction of alcohols with HX: (#1 synthesis of RX) R-OH + a) HX: HX
R-X + H2O HI > HBr > HCl b) ROH: 3o > 2o > CH3 > 1o c) May be acid catalyzed d) Rearrangements are possible except with most 1o alcohols. CH3CH2CH2CH2-OH + NaBr, H2SO4, heat CH3CH2CH2CH2-Br n-butyl alcohol n-butyl bromide 1-butanol
CH3CH2-OH + HI, H+, heat CH3CH2-I ethyl alcohol ethyl iodide ethanol iodoethane Mechanism? CH3-OH and most 1o alcohols react with HX via SN2 mechanism 3o and 2o react with HX via SN1 mechanism Both mechanisms include an additional, first step, protonation
of the alcohol oxygen: R-OH + H+ R-OH2+ oxonium ion Whenever an oxygen containing compound is placed into an acidic solution, the oxygen will be protonated, forming an oxonium ion. Mechanism for reaction of an alcohol with HX: CH3OH or 1o alcohols: SN2 1) 2) R-OH X + +
R-OH2 HX R-OH2 RDS R-X + + X H2O Mechanism for reaction of an alcohol with HX: 2o or 3o alcohols: SN1 1) R-OH
2) R-OH2 3) R + + HX RDS X R-OH2 R R-X + H2O
+ X May be catalyzed by acid. SN2 rate = k [ ROH2+ ] [ X- ] SN1 rate = k [ ROH2+ ] Acid protonates the -OH, converting it into a better leaving group (H2O), increasing the concentration of the oxonium ion, and increasing the rate of the reaction. Rearrangements are possible (except with most 1o alcohols): CH3 CH3CHCHCH3 + HBr CH3 CH3CCH2CH3 OH Br
CH3 CH3CHCHCH3 OH2+ Br- CH3 [1,2-H] CH3 CH3CHCHCH3 CH3CCH2CH3 + + 2o carbocation 3o carbocation In the reaction of most 1o alcohols with HX you don't have to worry about the possibility of rearrangements. The mechanism is SN2 and does not involve carbocations. CH3CH2CH2CH2CH2-OH +
HBr, H+, heat 1-pentanol CH3CH2CH2CH2CH2-Br 1o alcohol: No rearrangement, SN2 1-bromopentane Most 1o? If large steric requirement CH3 CH3CCH2-OH + CH3 neopentyl alcohol HBr CH3 CH3CCH2CH3 Br 2-bromo-2-methylbutane
Acids. Taste sour (do NOT taste a chemical to test this) React with certain metals (Zn, Fe, Mg, etc.) to produce hydrogen gas . Changes litmus paper red. Conduct electricity. React with bases to form salts and water
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