1. Oxidation of alcohols [O] = oxidizing agent dichromate Cr 2 O 7 2- permanganateMnO 4 - oxidation = aldehyde 1 o alcohol carboxylic acid 1. binding O 2. removing H loss of e - density from C 1+ 2- 1+ 3+ 2- 1+ 1- 1+ 2- Cr 3+

2. Alcohols oxidation of alcohols: [O] = Cr 2 O 7 2- or MnO 4 2- 1 o alcohols [O] aldehydecarboxylic acid [O] Cr 2 O 7 2- + +Cr 3+ [O] methanol formaldehyde [O] formic acid methanal methanoic acid

3. Alcohols oxidation of alcohols: [O] = Cr 2 O 7 2- or MnO 4 2- 2 o alcohols [O] ketoneno reaction [O]

4. Alcohols oxidation of alcohols: [O] = Cr 2 O 7 2- or MnO 4 2- 3 o alcohols [O] no reaction

5. H 2 SO 4 Condensation two molecules combine to form larger molecule + water alcohol ether H2OH2O + + CH 3 – OH + HO – CH 3 CH 3 – O – CH 3 + H 2 O Reaction Alcohols

6. Ethers R water alcohol ether -- H-bond acceptor O-O- no H-bond donordipole-dipole interactions low b.p. soluble in polar solvents

7. Ethers Common nomenclature :name both R groups + ether 1 2 3 1 propyl methy l ethermethyl propyl methyl dimethyl ether propyl peopleether O “ether” bunny..

8. Ethers Reactions Formation: H 2 SO 4 condensation reaction Peroxide formation: peroxide

9. Aldehydes and Ketones C=O carbonyl group aldehyde ketone C and O are sp 2 hybridized 120 o

10. Aldehydes and Ketones Nomenclature 1. Longest chain with C=O is parent 2. Suffix is “-al” or “-one” 3. C 1 is always C=O in aldehydes In ketones, C=O is given lowest number 4. C=O has precedence over -OH (called “hydroxy”)

11. 1 2 3 4 albutan2-bromo-3-methyl one 1 2 3 4 5 pentan 3- cyclobutanone 1 2 3 2-methyl 3-hydroxy- trans-

12. Physical properties -- ++ polar higher b.p. than alkanes H-bond acceptor soluble in polar solvents no H-bond donor lower b.p. than alcohols O.. C H H O C H H : + -

13. Reactions Reduction [R] = reducing agent LiAlH 4 NaBH 4 H 2 /Pt [R][R] [R][R] al one CH 3 - 1 2 34 butan CH 2 - CHOCH 2 - OH 1 2 34 butan2-