ALCOHOLS, ESTHER, AND THIOLS:

Alcohols:
 Organic compounds that contain a hydroxyl group (-OH)
 Classified by the number of carbon atoms directly bonded to the carbon attached to the
hydroxyl group
o Primary alcohol - 1 C atom bonded to C-OH
o Secondary alcohol - 2 C atoms bonded to C-OH
o Tertiary alcohol - 3 C atoms bonded to C-OH

Properties of Alcohols:
 Polar molecule
o b/c of ΔEN of C-O bond and O-H bond
 Capable of hydrogen bonding
 High boiling point and melting point
o Due to strong intermolecular forces and high polarity
 Alcohols with short hydrocarbon chains are soluble in water
o Less soluble with longer hydrocarbon chains

Naming Alcohols:
 Use the same rules as alkanes, alkenes, and alkynes
 Replace the final –e with –ol 
o Use di, tri, etc. to indicate the number of –OH
o Use numbers to indicate the carbon the –OH is bonded to
 For rings, -OH is on the first carbon

Practice for Alcohols:

Example:
a) 5,6-diethyl-2,7-dimethyloctane-3,4-diol 

b) 4-chloro-5-cyclopentyl-2-hexanol 

E T H E R S:

 Organic compounds that has an oxygen atom bonded between two carbon atoms

Properties of Ethers:
 Slightly higher m.p. and b.p. but lower than alcohols
o C – O bond is polar, but not capable of H-bonding
 Useful Solvents
o Can dissolve highly polar substances and Less polar substances

Naming Ethers:
 Method #1:
o Find the longest chain
o Name both hydrocarbon chains 
o Consider shorter chain to be substituent and end with “oxy” instead of “yl”
 Remember to add the C number
o Longer chain is treated as the parent chain

 Method #2:
o Name both hydrocarbon chains 
 Longer chain ends with “ane/ene/yne”
o Add word “ether” 
 Cyclic ethers are named as oxacycloalkanes with the oxygen being at position 1 of the
chain

Practice for Ethers:

Examples:
a) 2-bromo-4-ethyl-3-(1-methylethoxy)hexane 

b) 2-ethyloxacyclohexan-3-ol 

T H I O L S:

 Organic compounds containing a sulfhydryl group (S-H)

Properties of Thiols:
 Strong odors
o Ex. Garlic, skunk smell, sewage
 B.p. and m.p. close to alkanes
o b/c nonpolar bonds and same intermolecular forces

Naming Thiols:
 Use the same rules as alkanes, alkenes, and alkynes
 To the ending (keep the e), add –thiol 
o Use di, tri, etc. to indicate the number of –SH
o Use numbers to indicate the carbon the –SH is bonded to
 For rings, -SH is on the first carbon