Organic Chem Chapt 17

 

 

What is an alcohol

 compounds that have their -OH group bonded to a saturated sp3 hybirdized carbon atom
What is a enol?
compounds with their OH group bonded to a vinylic sp2 hybirdized carbon
Does hydrogen bonding cause higher boiling points in alcohols and phenols or their alkane counterpart?
Alcohol and phenol have higher boiling point 
How do  alchols act as weak acids?
The dissaciate slightly in aqueous solution by donating a proton to water generating H3O and a Alkoxide (RO-) ion or phenoxide (ArO-) ion…
 
How do alcohols and phenols act as weak bases?
the reversibly protonated by strong acids to yield oxonium ions (ROH2 +) 
Smaller Ka & Larger pKa = more or less acidic?

 

 

Less Acidic

Are sterically hindered alkoxides more or less acidic than unhindered alkoxides?
Less acidic
Halogen substituents increase or decrease the acidity of an alcohol?
INCREASES acidity
-stabilizes an alkoxide ion by spreading out the charge over a larger volume
-Lowers pKa value 
Which are more acidic alcohols or phenols?
Phenols bc their corresponding phenoxide ions are resonance-stabilized
What type of reagents do alcohols react with?
alkali metals and strong bases [NaH, NaNH2, RMgX] 
Phenols that have substitients can be more or less acidic than phenols itself if….

the subs are…
e- withdrawing=more acidic (delocalize the neg charge)

e-donating=less acidic(bc concentrate the charge) 

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