Orgo 2 Chp 17: Alcohols and Phenols

OH attached to primary carbon

primary alcohol

OH attached to secondary carbon

secondary alcohol

OH attached to tertiary carbon

tertiary alcohol

hybridization of carbons to identify alcohols

sp3 hybridized

alcohols and phenols have high boiling points due to

hydrogen bonding

boiling points ____ as the number of carbons increase

increase

branching _____ boiling points

decreases

factors that affect alcohol activity

1. bulky alkyl groups: decrease acidity

2. electron withdrawing groups: increase acidity

phenols are more acidic than alcohols because the conjugate base is

stabilized by resonance

substituted phenols:

1. electron donating groups ? acidity due to…?

1. decrease acidity due to not helping in spreading out the negative charge (with resonance, electrons go towards the negative charge not good)

substituted phenols:

1. electron withdrawing groups ? acidity due to…?

1. increase acidity at the ortho and/or para position; these groups spread out the negative charge of the conjugate base through resonance. 

phenols are more acidic than alcohols

true

alcohols reduction of carbonyl compounds 

1. reagent: NaBH4, EtOH in H20 or acid

• only reduces ketones and aldehydes 

• uses any solvent (wet or dry)

• mild reducing agent

alcohols reduction of carbonyl compounds 

1. reagent: LiAlH4, dry ether in H20 or acid

• reduce ketones, aldehydes, carboxylate acids, and esters 

• dry solvents 

• strong reducing agent

alcohols reduction of carbonyl compounds 

1. ketones reduce to?

2. COOH reduces to?

3. aldehydes reduce to?

4. esters reduce to?

1. secondary alcohol

2. primary alcohol

3. primary alcohol

4. primary alcohol

alcohols from carbonyl + grignard reagent

1. alkyl halides give what as the product

2. esters give what as the product

3. carboxylate acids give what as the product

1. tertiary alcohols 

2. tertiary alcohols

3. alkanes