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18 Cards in this Set

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  • Back
alkene to alcohol
1. OsO4, NaHSO4 for two alcohols.
2. Hg(OAc)2, H2O, NaBH4 for OH on more substituted cation
3. BH3, H2O2, OH- for alcohol on less substituted cation
alkyl halides to alcohol
1 degree halide
SN@ reaction where OH- replaces halide on end and changes stereochemistry
alkyl halide to alcohol
3 degree halide
SN1 reaction
halide leaves leaving cation where water comes in an H+ leaves
alkyl halide to alcohol
2 degree halide
use carboxylic acid anion, replaces halide and changes stereochemistry
OH- then replaces the anion and keeps stereochemistry
Elimination of alcohols
3 degree alcohols
use H2SO4
makes double bond
elimination of alcohol
2 or 3 degree
-use POCl3 and pyradine
-lone pair on OH binds to P, releases a Cl
-loses H+
-lone pair on N on pyradine reacts with H to make double bond to release molecule on top = E2
Substitution
1 to 2 degree alcohols to halides
-use SOCl2 for Cl
-use PBr3 for Br
-both change stereochemistry
-lone pair on OH binds to S and loses Cl, releases H+ and takes back Cl to make the molecule leave
substitution
3 degree alcohols to halides
-use HBR or HCL
-lone pair on OH binds to H, makes it leave, and BR comes in to cation
Synthesis of sulfonates
use SO2ClCH3
-lone pair onOH binds to S, Cl leaves and so does H+
-makes good leaving group
-doesn't change stereochemistry until it leaves and you bring in a halide such as Br or Cl
alkene to alcohol
1. OsO4, NaHSO4 for two alcohols.
2. Hg(OAc)2, H2O, NaBH4 for OH on more substituted cation
3. BH3, H2O2, OH- for alcohol on less substituted cation
alkyl halides to alcohol
1 degree halide
SN@ reaction where OH- replaces halide on end and changes stereochemistry
alkyl halide to alcohol
3 degree halide
SN1 reaction
halide leaves leaving cation where water comes in an H+ leaves
alkyl halide to alcohol
2 degree halide
use carboxylic acid anion, replaces halide and changes stereochemistry
OH- then replaces the anion and keeps stereochemistry
Elimination of alcohols
3 degree alcohols
use H2SO4
makes double bond
elimination of alcohol
2 or 3 degree
-use POCl3 and pyradine
-lone pair on OH binds to P, releases a Cl
-loses H+
-lone pair on N on pyradine reacts with H to make double bond to release molecule on top = E2
Substitution
1 to 2 degree alcohols to halides
-use SOCl2 for Cl
-use PBr3 for Br
-both change stereochemistry
-lone pair on OH binds to S and loses Cl, releases H+ and takes back Cl to make the molecule leave
substitution
3 degree alcohols to halides
-use HBR or HCL
-lone pair on OH binds to H, makes it leave, and BR comes in to cation
Synthesis of sulfonates
use SO2ClCH3
-lone pair onOH binds to S, Cl leaves and so does H+
-makes good leaving group
-doesn't change stereochemistry until it leaves and you bring in a halide such as Br or Cl