Test 3 Flashcards Preview

CHEM 211 > Test 3 > Flashcards

Flashcards in Test 3 Deck (42):
1

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syn addition

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5

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trans glycol

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Syn addition

cis glycol

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7

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8

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syn addition

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9

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syn addition

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10

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anti-markovnikov

Br on less subs c

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11

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markovnikov= OH on most subs C

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12

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markovnikov= OH on most subs C

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13

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anti-addition

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14

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anti-addition

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15

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syn addition, anti-markovnikov=OH on less subs C

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16

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anti-addition

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17

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anti-addition

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18

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22

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Other alkylating agents can be used: MeO and MeS

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23

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K2Cr2O7 in aqueous H2SO4 may also be used

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24

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2o alchohol most likely via SN1 so stereochem lost

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26

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best with 1o alcohols

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27

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Best with 1o alcohols

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poor nucleophiles/weak bases

O with no formal charge

29

Good nucleophiles/weak bases

Cl-, Br-, I-, NC-, N3-, S-, Se- or CH3COO-, or N, S, Se with no formal charge

30

Good Nucleophile/strong base

31

1o Carbon, poor Nuc/weak base

no reaction

32

2o Carbon, poor Nuc/weak base

95% Sn1

5% E1

 

33

3o Carbon, poor Nuc/weak base

95% Sn1

5% E1

34

1o  or 2o Carbon, good Nuc/weak base

Sn2

35

3o Carbon, good Nuc/weak base

95% Sn1

5% E1

36

1o Carbon, good Nuc/strong base

E2 w/ tert-butyl-oxide (bulky base), otherwise Sn2

37

2o or 3o Carbon, good Nuc/strong base

E2

38

Sn2

One Step: Nucleophile joins alpha carbon and leaving group leaves alpha carbon, inversion of stereochem

39

Sn1

Step 1: leaving group leaves alpha carbon

Step 2: Nucleophile joins alpha carbon

racemization

40

E2

One step: Base takes Beta hydrogen, pi bond forms between alpha and beta carbons, leaving group leaves alpha carbon

-H and LG have to be antiperiplanar

41

E1

Step 1: Leaving group leaves alpha carbon

Step 2: Base takes Beta hydrogen, pi bond forms between alpha and beta carbons

both cis and trans are made

42

Good leaving groups

Cl, Br, I, N+, O+, P+, S+, sulfonate