organic chemistry 5: Alcohols

[...] use suffix –ol or prefix hydroxy-

alcohols

• contains an -OH group

• - alcohols have a higher priority than double or triple bonds

1º, 2º, and 3º alcohols are named according to the number of carbons attached to [which carbon]

the carbon bearing the hydroxyl group

• in other words where the hydroxyl is bound to a primary, secondary, or tertiary carbon

This is a [primary, secondary, or tertiary] alcohol

primary

This is a [primary, secondary, or tertiary] alcohol

secondary

This is a [primary, secondary, or tertiary] alcohol

tertiary

This compound is known as a/an [...]

phenol

• benzene ring with -OH group attached

• - named for the relative position of the -OH group

The substituents on this benzene ring are in [...] position

ortho position

The substituents on this benzene ring are in [...] position

meta

The substituents on this benzene ring are in [...] position

para

[...] are conjugated cyclic diketones but are not aromatic

quinnes

• synthesized through oxidation of phenols

• examples

  • vitamin k1 (phylloquinone)

  • vitamin k2 (the menaquinones)

[...] are produced by oxidation of quinones

hydroquinones

• adds a variable number of hydroxyl groups

[...] is a biologically active quinone that acts as an electron acceptor in complexes I, II, and III of the electron transport chain

ubiquinone

• also called coenzyme q

• it is reduced to ubiquinol

When an alcohol is oxidized it becomes one of the following compounds:

[...]

[...]

[...]

aldehyde

ketone

carboxylic acid

• oxidation of an alcohol removes the H and adds a second bond to the O to make a carbonyl

Treatment of an alcohol with pyridinium chlorochromate (PCC) leads to the formation of a/an [...]

aldehyde

• any stronger xidinind agent will oxidize the alcohol all the way to carboxylic acid

-OH is a [good or bad] leaving group

bad

Alcohols can be converted to [...] or [...] to make them better leaving groups for nucleophilic substitution reactions

mesylates or tosylates

Aldehydes and ketones be protected by converting them into [...] or [...]

acetals or ketals

This is a/an [...]

acetal

• a primary carbon with two -OR groups anad a hydrogen atom

This is a/an [...]

ketal

• a secondary carbon with two -OR groups