1. Carboxylic Acids - Reactions
Acid-base reactions:
LDF
H-bonding
ion
+ NaOH
Na+
+ H2O
octanoic acid
sodium octanoate + water
insoluble in H2O
soluble
dipole

2. Reactions Reduction: 5-oxo hexanoic acid 1,5- hexanediol 5-hydroxy
LiAlH4 6 5 4 3 2 1
5-oxo
hexanoic acid
1,5-
hexanediol
H2/ Pt
NaBH4
5-hydroxy
hexanoic acid

3. Reactions nucleophilic substitution condensation reaction reverse =+
+ H2O
carboxylic acid
alcohol
ester
condensation reaction
reverse =
hydrolysis H+ +
ester
+ H2O
carboxylic acid
alcohol

4. Esters from alcohol from acid name = alkyl group from alcohol (yl)
acid name changed to “oate”
methyl
butanoate
apple
pentyl
butanoate
peaches

5. Esters H-bond acceptors O O no H-bond donor dipole-dipole interactions
water soluble
low b.p.

6. Carboxylic acids nucleophilic substitution condensation reaction..
activator +
+ H2O
carboxylic acid
amine
amide
condensation reaction
carboxylic acid +
amine
amide
+ H2O
hydrolysis reaction
amide
+ H2O
carboxylic acid +
amine

7. Amines N- H+ organic analogs of ammonia ammonia 1o amine 2o amine
all have H-bond acceptor
N-
1o and 2o have H-bond donor
H+
high b.p.
electronegativity
O N
liquid at room T
>
gas at room T

8. Amines nomenclature 1. Name and alphabetize R groups and add “amine”
methylamine 1o
ethyl
methyl
amine 2o
ethyl
dimethyl
amine 3o
low b.p.

9. Amines + H2O + OH- [R-NH3+] [OH-] smaller Kb weaker base Kb = [R-NH2]
weak bases
+ H2O
+ OH-
[R-NH3+]
[OH-]
smaller Kb
weaker base
Kb =
[R-NH2]

10. Amines Condensation reaction nucleophilic substitution +H2O +H2O
activator
+H2O
+H2O
no reaction +
amide
carboxylic acid
2o amine
1o amine
3o amine
amide
Condensation reaction

11. Amides C-O and C-N double bond character
very high b.p.
C-O
and C-N
double bond character
no rotation about C-O or C-N bonds
molecule is flat and rigid
structure of proteins