chapter 9 - alcohol, ether, epoxide rxns Flashcards

1
Q

dehydration rxns that form alkenes and H2O:
1.
2.

A
  1. strong acids: H2SO4 or TsOH

2. POCL3/Pyridine

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2
Q

SOCL2/Pyridine and PBr3 are always what mechanism?

A

SN2
1 degree and 2 degree

SOCl2 –> R-Cl
PBr3 –> R-Br

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3
Q

POCL3/Pyridine is always what mechanism?

A

E2
1 degree and 2 degree
no carbocation rearrangement!

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4
Q

Big bulky bases:

A

Na+-OtButyl
DBU
DBN

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5
Q

R-OH

A
  1. R-X (Cl, Br, I) = SN2

2. strong acid = E2

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6
Q

R2-OH and R3-OH

A
  1. R-X = SN1

2. Strong acid = E1

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7
Q

Tosylate: TsCl/Pyridine

A

makes R-OTs (good LG):

  1. strong nuc = SN2
  2. big bulky base = E2
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8
Q

alkene synthesis

A

E2
uses strong base:
NaNH2 or KOC(CH3)3/DMSO (solvent)

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9
Q

rxn with tosyl chloride to form alkyl tosylates

A

Cl atom is the LG and R-OH bonds to molecule. looses H

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10
Q

ethers

A
  • 2 equivalents (Br or I)
    R-X + R-X + H2O

2 degree and 3 degree = SN1
CH3 and 1 degree = SN2

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11
Q

epoxides

A
  • backside attack forms anti or trans products
  • Strong nuc = SN2 and nuc attack on less sub C
  • H-Nuc = substitution and nuc attack occurs on more sub C
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