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14 Cards in this Set
- Front
- Back
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Which is more acidic phenol or cyclohexanol and why
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Phenol is because the lone pair on the oxygen when the H+ leaves is stabalized with the delocalized electrons in the benzene ring.
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Name 5 ways to make an alcohol
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SN2 rxn where OH- attacks.
Acid catalyzed hydration oxymercuration-demercuration hydroboration-oxidation Syn di-hydroxolation from an alkene addition of acetylides to a ketone of aldehyde. Grignard reagent (R-Mg-X)in an ether Organolithium reagent with an alkyl halide |
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What is an organolithium reagent and how does it act
what is it used for |
R-Li
It acts like R- Li+ resembles a carbanion and is a strong nucleophile and a strong base. When 2Li are added to an alkyl halide one will take the halide and the other will replace it. Making something that acts like a carbanion. This can be used to add to a ketone and will add the R-group and turn the ketone into an alcohol. |
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How do organolithium agents and Grignard reagents produce alcohols
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They are strong nucleophiles that attack a carbon with a =O making an alkoxide. It will take H+ from water or an acid making the alcohol.
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What are Grignard reagents
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Alkyl halides that that have Mg added.
R-X goes to R-Mg-X which acts like a carbanion and becomes strongly nucleophilic and basic. |
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What happens if you add a Grignard reagent to an acid chloride or an ester
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It makes a tertiary alcohol.
1st time the reagent attacks carbon and makes the =O into -O. Then the R group attached by the ester leaves with the oxygen as R-O(-1). Another Grignard reagent attacks the carbon again making the =O a -O(-1). Then it gets protonated to make the tertiary alcohol. |
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Describe the reaction of a Grignard reagent with an ethylene oxide
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Attack by Grignard reagent on a carbon. This opens the ring and adds the R group is attached to one and O- is attached to the first carbon. When protonated in acid it becomes a primary alcohol
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What solvent do you need for Grignard reagents
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An ether (R-O-R)
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How do you reduce an alkyl halide to an alkane?
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Add Mg and it becomes a Grignard reagent. Add water and it reacts to make XMgOH and the alkane.
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What are some reducing agents and what will they reduce
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NaBH4 - aldehydes and ketones
LiAlH4 - aldehydes, ketones, acid chloride, esters |
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What will sodium borohydride reduce
What kind of solution can you use |
aldehydes and ketones
Many types including water and alcohols |
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What will lithium aluminum hydride reduce
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Aldehydes and ketones, esters, and carboxylic acids
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What is the result of adding LiAlH4
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everything except ethers become a primary alcohol. Ethers become secondary alcohols
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What is Raney nickel
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Reducing agent that reduces, aldehydes, ketones, and carbon carbon double bonds.
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