1. Carbonyl Compounds

2. Carbonyl Compounds Chap. 12
Carbonyl Containing Compounds
Nucleophilic Addition Reactions
Oxidation-Reduction (Redox) Reactions
Reducing Agents
Oxidation of Alcohols
Organometallic (Grignard Reagents) Note: overview only

3. Carbonyl Compounds

4. Carbonyl Compounds Formula Common Name Source IUPAC Name Melting Point
Boiling Point
HCO2H
formic acid
ants (L. formica)
methanoic acid
8.4 ºC
101 ºC
CH3CO2H
acetic acid
vinegar (L. acetum)
ethanoic acid
16.6 ºC
118 ºC
CH3CH2CO2H
propionic acid
milk (Gk. protus prion)
propanoic acid
-20.8 ºC
141 ºC
CH3(CH2)2CO2H
butyric acid
butter (L. butyrum)
butanoic acid
-5.5 ºC
164 ºC
CH3(CH2)3CO2H
valeric acid
valerian root
pentanoic acid
-34.5 ºC
186 ºC
CH3(CH2)4CO2H
caproic acid
goats (L. caper)
hexanoic acid
-4.0 ºC
205 ºC
CH3(CH2)5CO2H
enanthic acid
vines (Gk. oenanthe)
heptanoic acid
-7.5 ºC
223 ºC
CH3(CH2)6CO2H
caprylic acid
octanoic acid
16.3 ºC
239 ºC
CH3(CH2)7CO2H
pelargonic acid
pelargonium (an herb)
nonanoic acid
12.0 ºC
253 ºC
CH3(CH2)8CO2H
capric acid
decanoic acid
31.0 ºC
219 ºC
Source:

5. Nucleophilic Addition Reactions

6. Nucleophilic Addition Reactions

7. Oxidation-Reduction (Redox) Reactions

8. Redox Reactions Oxidation: Loss of electrons
Increase Oxygen
Decrease Hydrogen
Reduction: Gain of electrons
Increase Hydrogen
Decrease Oxygen

9. Reducing Agents

10. Reducing Agents LiAlH4 NaBH4 Work problem 12.1, Page 540
Lithium Aluminum Hydride
Stronger reducing agent
Reduces all carbonyl groups to alcohols
NaBH4
Sodium Borohydride
Weaker reducing agent
Reduces only ketones & aldehydes to alcohol
Work problem 12.1, Page 540

11. Alcohol Dehydrogenase

12. Oxidation of Alcohols PCC KMnO4 H2CrO4 Primary alcohols to aldehydes
Primary alcohols to carboxylic acids
H2CrO4
Secondary alcohols to ketones

13. Oxidation of Alcohols (PCC)
Primary alcohols to aldehydes

14. Oxidation of Alcohols (KMnO4)
Primary alcohols to carboxylic acids

15. Oxidation of Alcohols (H2CrO4)
Secondary alcohols to ketones

16. Chemical Test for 10 & 20 Alcohols
Distinguishes primary and secondary alcohols from all functional groups except aldehydes
Problem 12.3, Page 547
Problem 12.12, 12.17, Page 563

17. Organomagnesium Compounds
Discovered by the French chemist Victor Grignard in 1900 (Nobel Prize, 1912)
Now called Grignard Reagents
Formed from free radical reactions
Related to organolithium compounds
Create nucleophilic R-groups

18. Organomagnesium Compounds