Answers 1

 
Some  Practice  Problems  for  the  Amines/Acids  Test  4  
Draw  the  Mechanisms  for  the  following  Reactions  
Page  4  has  some  synthesis-­‐design  practice  problems.  
 
 
Br (excess) 1. SN2
NH N 2. Deprotonatate
1. NaOH 3. SN2

NH 2 Me Br (excess) Me Me
N 1. SN2
NaOH Me 2. Deprotonatate
3. SN2
2.   4. Deprotonate
5. SN2

NH 3 (excess)
Br NH 2 + NH 4Br
3.   1. SN2
2. Deprotonatate

O O
NH 3 (excess)
Cl NH 2 + NH 4Cl 1. Add
4.   2. Eliminate
3. Deprotonatate

O
O
NH + NaOH 1. Add
Cl
N 2. Eliminate
5.   3. Deprotonatate
   2  

O
O
NaOH 1. Add
Cl + H 2N
2. Eliminate
N
6. H   3. Deprotonatate

O
O 1. Protonate
T H+
OH + HO 2. Add
7. O   3. Deprotonatate
4. Protonate
2. Eliminate
3. Deprotonatate

H+ 1. Protonate
OH 2. Add
O
3. Deprotonatate
OH O 4. Protonate
8. O   2. Eliminate
3. Deprotonatate

O O
H+
+ H 2O HO 1. Protonate
OH +
9. O   2. Add
3. Deprotonatate
4. Protonate
2. Eliminate
3. Deprotonatate

+ H 2O H+ OH
O 1. Protonate
OH O 2. Add
3. Deprotonatate
10. O   4. Protonate
  2. Eliminate
  3. Deprotonatate
 
 
 
 
   3  
 
Ph Cl + H 2O Ph OH 1. Add
2. Eliminate
O
11. O   3. Deprotonatate

Ph O Ph + HO Ph O + HO Ph

T O 1. Add
12. O O O   2. Eliminate
3. Deprotonatate

O
NH 2 O HN + MeOH 1. Add
2. Eliminate
13. OMe   3. Deprotonatate

O
OH NH 2 O 1. Add
HN 2. Eliminate
O 3. Deprotonatate
14.  

1. NaOH, H 2O
Ph O Ph Ph OH + HO Ph 1. Add
2. H + 2. Eliminate
15. O O   3. Deprotonatate
4. Reprotonate with acid
   4  
Design Syntheses for the following transformations

OH N
16. H  

O O

NMe 2 O
T 17.  
 
 
 
 
OH HN Ph

18.  
 
 
 
 
O
Br
19. O  

OH NH

20.  
 
 
 
 
O O
Ph N
Ph O Ph
21.  
 
 
 
 
O O
Br Ph O
Ph
22.