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CHEM231 :D > Exam III > Flashcards

Exam III Flashcards

1
Q

SN2

A

bimolecular
inversion of configuration (R -> S)
1 step done
aprotic solvent

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2
Q

SN1

A

unimolecular
step-wise
racemic
protic solvent

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3
Q

Alcohols & PCC

A

1 Aldehyde
2 Ketone
3 no rxn

weaker than Jones Reagent

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4
Q

E2

A

anti-periplanar
strong bases
one step

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5
Q

E1

A

presence of weak bases (CH3-OH, H2O)
two step
LG better on axial position (idc about antiperiplanar)

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6
Q

Strong Nucleophiles

A

Br-, I-, CH3S-, OH-,
RS-, OR-, R-C=_C-,
CN-, N3-

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7
Q

Good Nucleophiles

A

Cl-, F-, CH3-C(=O)-O-, R-C(=O)-O-
CH3SH, RSH, R2S,
NH3

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8
Q

Bad nucleophiles

A

H20, ROH, R-C(=O)-OH

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9
Q

Alcohol Reduction

A

oxygen loss
hydrogen gain

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10
Q

Alcohol Oxidation

A

oxygen gain
hydrogen loss

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11
Q

Alcohol Substitution

A

make good leaving group (sn2)

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12
Q

Alcohols & Jones Reagent

A

1 RCOOH
2 Ketone
3 NR

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13
Q

How to make ethers

A

Alkane Oxymercuration
Williamson Ether Synthesis (Na-NH3)
H2SO4

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14
Q

How to make epoxides

A

McPBA
X2, base

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15
Q

How to open epoxides

A

Basic (less substituted)
Acidic Conditions (more substituted)
LiAlH4

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16
Q

Alkane oxymercuration

A

Mark, Syn
Used to make ethers

17
Q

Williamson Ether synthesis

A

SN2, NaR, Na0, NaH

18
Q

Ether Cleavage

A

SN2 - HI
SN1 - HBr

19
Q

KOH

A

E2 on alkyl halides

20
Q

H2SO4

A

E1 on alcohols

21
Q

Hoffman major

A

no hydrogen on anti to leaving group on cyclohexane

22
Q

aprotic solvent

A

SN2, cannot hydrogen bond
DMSO, DMF, acetone, ACN, CH2Cl2, DCM, THF

23
Q

protic solvent

A

SN1, can hydrogen bond
H2O, HCOOH, CH3OOH, EtOH, CH3COOH

24
Q

Alcohol (mechanism)

A

H2O (know mechanism)

25
Q

SN2 LG ranking

A

primary is better

26
Q

SN1 LG ranking

A

tertiary is better

27
Q

hydroboration

A

anti-mark, synaddition

28
Q

oxymercuration

A

anti-mark, anti addition

CHEM231 :D (5 decks)

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