Alcohols and Phenols

Question 1

-OH group(s) attached to a benzene ring

Answer 1

phenols

Question 2

Nomenclature of Phenols

Answer 2

Named by the relative position of -OH groups. In order of closest to furthest, it goes ortho, meta, para.

Mnemonic: the -OH groups like to ROMP around the benzene ring.

Question 3

Differences of phenols from other alcohols

Answer 3

Phenols are more acidic because the benzene ring helps stabilize negative charges.

Question 4

Produced by oxidation of phenols.

Answer 4

Quinones

Question 5

A type of quinone, also called coenzyme Q, that is biologically important because it accepts electrons in the ETC and is reduced to ubiquinol.

Answer 5

Ubiquinone

Question 6

Alcohols

Primary alcohol oxidation

Answer 6

Oxidized to aldehyde by PCC.

Oxidized to carboxylic acids by stronger oxidizing agents (ie Jones reagent).

Mild oxidizers like Tollen’s reagent will selectively oxidize aldehydes but not ketones or alcohols

Question 7

Alcohols

Nomenclature

Answer 7

Named using -ol (if highest priority functional group) or otherwise hydroxy-
Primary, secondary, or tertiary depending on how many other C are attached to the carbon with the -OH group.

Question 8

Alcohols

Secondary alcohol oxidation

Answer 8

Oxidized to ketone by any oxidizing agent.

Question 9

Alcohols

Leaving group conversion

Answer 9

Alcohols can be converted to sulfonates such as mesylate or tosylate which are very good leaving groups for nucleophilic substitution reactions.

Question 10

Alcohols

Acetal / ketal conversions

Answer 10

Alcohols protect aldehydes or ketones by reacting and converting them to acetal or ketal, respectively.