Kaplan Organic Chemistry: Chapter 5 Alcohols Flashcards
T/F: Hydroxyl H’s of phenols are more acidic than those of other alcohols. Why or why not
True. they are more acidic because the presence of alkyl groups donate electron density, and they destabilize the negative charge.
the alkoxide ion is resonance stabilized in a phenol ring system, making the OH more likely to deprotonate into O-
primary alcohols can be oxidized to form ____ with PCC
aldehyde
primary alcohols can be oxidized to form ____ with chromates
carboxylic acids.
secondary alcohls can be oxidized to form ___ with PCC
ketones.
What is a jones oxidation
primary alcohols can be oxidized to form carboxylic acids with a strong oxidizer and sulfuric acid. secondary alcohols can be oxidized to ketones.
what is the functional group of mesylate/tosylates
-SOCH3
purpose of mesylates and tosylates
hydroxyl groups are poor leaving groups for a nucleophilic substitution reaction because an OH- is a strong base and unstable. a mesyl or tosyl group can serce as a protecting group when we do not want alcohols to react.
how can an alcohol act as a protecting group for aldehydes and ketones?
aldehydes and ketones can be reacted with TWO equivalents of alcohol, or one diol, to form an acetal and ketal.
acetal and ketals are inert, and will allow you to react(reduce) any carboxylic acids on the same compound while conserving the aldehydes and ketones
after the reaction occurs, the acetal and etal can be reverted back to a carbonyl with ACID –> deprotectation.
the treatment of phenols with oxidizing agents produces compounds called:
QUINONES.
biological purpose of quinones
often as electron acceptors.
quinones can be further oxidized to form. are they more nucleophilic or electrophilic than quinones?
hydroxyquinones. less electrophilic.
