1. Alcohols, Ethers & Thiols
Singly Bonded Oxygen

2. Alcohols Structure Alcohols contain a hydroxyl group (-OH)
Oxygen is sp3 hybridized, with bent geometry
OH bond is polar, so smaller alcohols are soluble in water
1º, 2º, 3º Alcohols

3. Alcohols

4. Alcohol Nomenclature Suffix –ol
Gets numbering priority over double bonds
Hydroxyl carbon must be numbered (C3 or higher)

5. Nomenclature & Physical Properties
High boiling compared to similar MW alkanes due to hydrogen bonding
Higher MW alcohols have higher MP/BP

6. Physical Properties & Reactions
C1-C3 alcohols miscible with water
Reactions of alcohols
Acid catalyzed dehydration to alkenes

7. Reactions Ease of dehydration: 3º>2º>1º Mechanism – ionic
Water is a good “leaving group”

8. Reactions Orientation of elimination: Zaitsev’s Rule
Elimination will predominately give the most substituted alkene

9. Reactions Oxidation to aldehydes and ketones
During double bond formation both carbons have a partial + charge
Oxidation to aldehydes and ketones
Primary alcohols are oxidized to aldehydes
Secondary alcohols are oxidized to ketones

10. Reactions
Rxn w/ acids esters

11. Ethers Structure – contain C-O-C group – bent geometry like water
Nomenclature
Common names almost always used
Name both groups attached to oxygen, and end both names in –yl

12. ethoxyethane (diethyl ether)
Ethers
Common usage – groups ranked in size order
IUPAC – OR is named as an alkoxy group
CH3CH2OCH2CH3
ethoxyethane (diethyl ether)
Physical properties – lower BP, less solubility in water than isomeric alcohols – no H bonding
Ethers are relatively inert

13. Williamson ether synthesis

14. Thiol structure and nomenclature
Contain sulfydryl group (-SH)
They are sulfur analogs of alcohols
Sulfur is sp3 hybridized, with S-H bond angles of about 100º (big lone pairs)
Nomenclature
Suffix is –thiol. The “e” of the parent carbon chain is not dropped.

15. Thiol nomenclature
Older name – “mercaptan”
CH3SH methyl mercaptan

16. Thiol reactions Precipitation with mercury salts
2CH3SH + Hg+2  (CH3S)2Hg
Oxidation to disulfides