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29 Cards in this Set

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Why are the hydroxyl hydrogens of phenols more acidic than those of alcohols?
B/c of resonance structures that distribute the negative charge throughout the ring, thus stabilizing the anion.
A phenol will have a higher/lower Ka than a straight chained alcohol.
Higher Ka, smaller pKa.
Strong acids have high Ka's and small pKa's.
Electron withdrawing groups increase/decrease acidity.
Increase. They stabilize the anion, making the alcohol more acidic.
Electron donating groups increase/decrease acidity.
Decrease.
1' ROH are mildly oxidized to...
Aldehydes
2' ROH are mildly oxidized to ....
Ketones
1' ROH are strongly oxidized to ....
Carboxylic acids
Carboxylic acids are mildly reduced to...
Aldehydes
Carboxylic acids are strongly reduced to ...
1' Alcohols
Ketones are reduced to ...
2' Alcohols
What are the 2 most frequently used reducing reagents?
1. NaBH4 - more selective, easier to handle
2. LAH - more powerful and difficult to work with
Phenols can be synthesized via hydrolysis of ...
diazonium salts
Alcohols can be dehydrated in a stongly acidic solution to produce alkenes. The mechanism of this dehydration is E1/E2 SN1/SN2.
E1 and proceeds via the protonated alcohol. Major product is the more substituted.
Protonating an alcohol makes water the leaving group, which is good for SN1 reactions, even better, the alcohol can be converted to ______ which is good for SN2 rxns.
Tosylate aka p-toluenesulfonate
PCC role in reactions
mild oxidant
KMnO4 role in reactions
strong oxidant
Na2Cr2O7 role in reactions
strong oxidant
What is a Jones Reagent?
CrO3, H2SO4 in acetone
very strong oxidant
What oxidizes 1' ROH to COOH and 2' ROH to RCOR?
Jones Reagent
Treatment of phenols with oxidizing agents produces...
quinones
Ethers are __________ polar and therefore ____________ soluble in water.
Slightly/slightly
Williamson Ether synthesis creates ethers from ...
the reaction of metal alkoxides with 1' alkyl halides or tosylates
Williamson Ether synthesis proceeds via E1/E2 SN1/SN2
SN2. Alkoxides only attack nonhindered halides. Thus to synthesize a methyl ether, an alkoxide must attack a methyl halide; not the other way around (too hindered).
Oxidation of an alkene with a peroxy acid such as mcpba produces...
Oxirane
Which of the following reagents should be used to convert CH3(CH2)3CH2OH into CH3(CH2)3CHO?
a. KMnO4
b. Jone's reagent
c. PCC
d. LAH
C. The best way to prepare RCOH from 1' ROH is to use PCC. KMnO4 is a strong oxidizing agent and converts a 1' to a COOH. Jone's reagent is a very strong oxidizer. LAH is a reducing agent, and will not oxidize an alcohol.
Since epoxides are highly strained cyclic ethers, they are susceptible to cleavage via E1/E2 SN1/SN2 reactions.
SN2. Can be acid or base catalyzed.
Epoxide cleavage can be acid or base catalyzed. The most substituted carbon is attacked in the presence of an....
Acid
Epoxide cleavage can be acid or base catalyzed. The least substituted carbon is attacked in the presence of an....
Base. Base catalyzed cleavage has the most SN2 character, so it occurs at the least hindered carbon.
Tertiary ROH's are oxidized with difficulty because
There is no hydrogen attached to the carbon with the hydroxyl group.