Test 3 Flashcards
1
Q
A
2
Q
A
3
Q
A
syn addition
4
Q
A
5
Q
A
trans glycol
6
Q
A
Syn addition
cis glycol
7
Q
A
8
Q
A
syn addition
9
Q
A
syn addition
10
Q
A
anti-markovnikov
Br on less subs c
11
Q
A
markovnikov= OH on most subs C
12
Q
A
markovnikov= OH on most subs C
13
Q
A
anti-addition
14
Q
A
anti-addition
15
Q
A
syn addition, anti-markovnikov=OH on less subs C
16
Q
A
anti-addition
17
Q
A
anti-addition
18
Q
A
19
Q
A
20
Q
A
21
Q
A
22
Q
A
Other alkylating agents can be used: MeO and MeS
23
Q
A
K2Cr2O7 in aqueous H2SO4 may also be used
24
Q
A
2o alchohol most likely via SN1 so stereochem lost
25
26
best with 1o alcohols
27
Best with 1o alcohols
28
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
