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Reactions
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18
Chemistry
Not Applicable
05/15/2005

Additional Chemistry Flashcards

 


 

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Term
Acid-Base Properties of Alcohols
Definition
Alkloxonium ions
(H+)
ROH
(B- (base))
Alkoxide
Term
Acidity levels
Definition
R-OH ~ HO-H > H2N > H3CH
Term
Bascitiy
Definition
RO- ~ HO- > H2NH > H3CH
Term
Nucleophilic displacement of Halides and Other leavying groups by hydroxide :
Definition
RCH2CX + HO- goes to RCH2 OH + X- through water and Sn2 rxn
Term
Reduction of Aldehydes
Definition
Use: NaBH4 in CH3CH2OH to get a primary alcohol

Use: LiAlH4 in (CH3CH2)2 and water work up to get a primary alchol
Term
Reduciton of Ketones
Definition
Use: NABH4 in CH3Ch2OH
Use: LiAlH4 in (Ch3Ch2)2O and water work up

This process yields a secondary alchol
Term
Oxidation of Primary Alchols
Definition
Use PCC In CH2Cl2 to get an aldehyde
Term
Oxidation of Secondary Alchols
Definition
Use Na2Cr2O7 in H2So4 to get a ketone
Term
Organometallic Reacents- reaciton of metals with haloalkanes
Definition
RX + Li in (CH3Ch2)2O yieldds a RLi which is a alkyllitium reagent
Term
organometallic reacents
Definition
RX + Mg yields RMgX in (Ch3Ch2)O R cannot contain acidic groups sh=uch as OH or electrophilic groups such as c=O
Term
Hydrolysis
Definition
RLi or RMGX + water yields RH

RLi or RMgX + D2O yields RD

Aldehyde or ketone cannot contain other groups tha treact with organometallic reagents such as OH or othe rC=O groups
Term
Reaction of Organometallic Compounds to Aldehydes and Ketones
Definition
RLi or RMgX + CH2=O yields primary alchols

RLi or RMgX + Aldehyde yields secondary alcohols

RLi or RMgX + Ketone yields a tertiary alcohol
Term
Alkanes from Haloalkane and Litium Aluminum Hydride
Definition
RX + LiAlH4 yields RH (in Ch3CH2)2o
Term
Alkanes from Haloalkane and Litium Aluminum Hydride
Definition
RX + LiAlH4 yields RH (in Ch3CH2)2o
Term
Alkoxides from alcholss:
Definition
ROH + M yields ROM + 1/2 H2

M= Li, Na, K
Term
Using Hydrogen Halides to give you HBaloalkanes from Alchols
Definition
Primary ROH uses a concentrated haloalkene (HX, where H is Br or I , in an Sn2 mechanism)

Secondary or Tertiary ROH in concentrated HX ( where X is Cl, BR, or I as a SN1 mechanism) to yield RX
Term
Using phospohorous reagents:
Definition
3 ROH + PBr3 yields 3RBr + H3PO3
6ROH + 2 P + 3I2 yields ^ RI 2 H3PO3

Sn2 mechanism with primary and scondary ROH
less likelihood of carbocation rearrangements that with HX
Term
Using Sulfur Reagents
Definition
ROH + SOCL3 in ( N Ch2CH3)2 yields RCl + SO2 + (CheCh2)3 NHCl

ROH + R'So2Cl yields ROSO2R' yields NuDMSO RNu + R'So3-
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