Chap 10 Alcohols

Chap 10 Alcohols - Alcohols Hydrogen Bonding Three ethanol...

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Alcohols
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Hydrogen Bonding Three ethanol molecules.
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Increases boiling point, higher temperature needed to separate the molecules. Hexane 69 deg. 1-pentanol 138 1,4-butanediol 230 Ethanol 78 deg Dimethyl ether 24
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Earlier Discussion of Acidity Methanol Ethanol 2-Propanol 2-Methyl-2-propanol Increasing Hinderance of Solvation RO-H RO (solvated) + H + (solvated) Increasing Acidity of the alcohol Recall: H 2 O + Na Na + + OH - + ½ H 2 (g) Alcohols behave similarly ROH + Na Na + + OR - + ½ H 2 (g) Alkoxide, strong base, strong nucleophile (unless sterically hindered) Also: ROH + NaH Na + + OR - + ½ H 2 (g) Increasing Basicity of Alkoxide Anion, the conjugate base Alkoxide ion, base Alkoxides can be produced in several ways…
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-OH as a Leaving Group R-OH + H + R-OH 2 + Protonation of the alcohol sets-up a good leaving group, water. Poor leaving group, hydroxide ion. Another way to turn the –OH into a leaving group…
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Conversion to Alkyl Halide, HX + ROH RX + H 2 O When a carbocation can be formed (Tertiary, Secondary alcohols) beware of rearangement. S N 1 Expect both configurations. When a carbocation cannot be formed. Methanol, primary. S N 2 RCH 2 OH RCH 2 OH 2 X - H + RCH 2 X R 3 COH R 3 COH 2 R 3 C + + H 2 O X - H + R 3 CX
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This note was uploaded on 12/05/2011 for the course C 341 taught by Professor Skagg during the Spring '11 term at Indiana.

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Chap 10 Alcohols - Alcohols Hydrogen Bonding Three ethanol...

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