Organic Chemistry II
Organic Chemistry II
Organic Chemistry II
I. Nomenclature
A. Functional Groups
1) RCH2—OH = Hydroxy functional group
2) Alcohol = organic molecule having a hydroxy group
3) Replace one H of water with R: H—O—H R—O—H
4) Ether = replace both H’s of water with R: R—O—R
B. Naming Alcohols
1) Modify the alkane name by dropping –e and adding –ol
a) CH3OH = methanol
b) CH3CH2CH2CH2OH = butanol
c) R-OH = alkanol
2) Branched Alcohols OH OH
OH
HO H OH
1-propanol (S)-3-hexanol 2,2,5-trimethyl-3-heptanol
-
B. Hydrogen Bonding
1) Hydrogen bond = weak, partial bond between a heteroatom bound H and
another heteroatom (N, O, X, S, etc…)
2) DHo(OH…..H) = 5 kcal/mol
~ 0% 99.999%
5) Acidity: MeOH > 2-Propanol > t-Butyl Alcohol (1o > 2o > 3o)
Steric disruption of solvation
of deprotonated product
6) Inductive Effects = transmission of charge through s-bonds
a) Electronegative substituents increase an alcohol’s acidity
CCl3CH2OH > CHCl2CH2OH > CH2ClCH2OH > CH3CH2OH
C. Basicity of Alcohols
1) Lone pairs of electrons will accept H+ from strong acids
ROH + HA ROH2+ + A-
weak Strong
base Conjugate
Acid pKa = -2
O -
O
OH
CH3CH2O CCH3 CH3CH2OH + HO C CH3
Ester Hydrolysis Acetic acid
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