Organic II Exam #2 Ch 18-20 (100 points). NAME: 1) Name the ...
Organic II Exam #2
Ch 18-20
(100 points).
NAME:
1)
Name the general class of organic molecules that each of these molecules belong to, and circle the most reactive molecule with respect to undergoing nucleophilic attack. (11pts) R O
O
R C R
R C H
O R C NH2
2)
O R C OH
R C N
H2C CH2 CN O O HO C C R R R R
Ph Ph O P Ph R C C R R R
Circle the stronger base in the following pairs, and in a sentence explain your choice. (6pts)
NH2
(a)
(b)
R NH2
N R C R
H3C N H
O C
CH3
NH2
H3C N H
Org II Exam 2
H2 C
CH3
Page 1
3) Circle the stronger acid in the following pairs, and in a sentence explain your answer. (12pts) O (a)
H3C C OH
CH3CH2 OH
O
O
(b)
H3C C OH
F3C C OH
(c)
O Br3C C OH
O F3C C OH
(d)
O C OH
O CH3CClH C OH
CClH2CH2
Org II Exam 2
Page 2
4)
Name the following compounds in IUPAC acceptable terms. (15pts) O Br
C C
H CH3
O
O
Ph H
NH
H CO2H
Org II Exam 2
Page 3
5)
Explain why propanal is more reactive than propanone towards nucleophilic attack. (10pts)
Org II Exam 2
Page 4
6) The following is taken from a forthcoming publication in the Journal of Organic Chemistry, where a bright young chemist is using classic Diazonium salt chemistry to functionalize some fluorinated cyclophanes. However he was distracted by the wrestling on the TV and left some blanks in his report, help him by filling in the missing products or reagents. (15pts) F F F F
F F F F
F F F F
?
F F F F
NO2
NH2
?
?
H2O, H2SO4 heat
F F F F
F F F F +
N2 Cl
-
1) HBF4 CuBr
2) heat
?
?
?
F F F F
F F F F CO2H
Org II Exam 2
Page 5
6) Give the products formed in five of the following reactions. (15pts) (a)
O Ph C Ph
(b)
O Ph C Ph
1) PhMgBr
O Ph C Ph
1)Ph3P, CH3-Br
(c)
H3C NH2
H+
2) H3O+
2) BuLi 3) warm
(d)
(e)
H3C NH2
H3C NH2
excess CH3CH2CH2-Br
O excess H3C C Cl
NH2 (f)
1) excess CH3-Br 2) Ag2O, H2O, heat
Org II Exam 2
Page 6
7) Give reagents for the following oxidations and reductions, bearing in mind the (in)compatibility of some of the functional groups. (9pts) O H3C C
O
O
O
C OH
H3C C
CH2-OH
O
OH H3C CH
O
O H3C C
O
H3C C
C H
O H3C C
O C H
C H
C OH
8) Methylamine has pKb = 3.36 an ammonia has pKb = 4.74. Indicate which is the stronger base, and explain why one is a stronger base than the other. (7pts) Or Write both the mechanisms for the acid and base catalyzed hydration of acetone. (also 7pts)
Org II Exam 2
Page 7
*Bonus question* (up to 4pts) Why are the basicities of methylamine and trimethylamine about same? (use back if necessary).
Org II Exam 2
Page 8
Ch 18-20
(100 points).
NAME:
1)
Name the general class of organic molecules that each of these molecules belong to, and circle the most reactive molecule with respect to undergoing nucleophilic attack. (11pts) R O
O
R C R
R C H
O R C NH2
2)
O R C OH
R C N
H2C CH2 CN O O HO C C R R R R
Ph Ph O P Ph R C C R R R
Circle the stronger base in the following pairs, and in a sentence explain your choice. (6pts)
NH2
(a)
(b)
R NH2
N R C R
H3C N H
O C
CH3
NH2
H3C N H
Org II Exam 2
H2 C
CH3
Page 1
3) Circle the stronger acid in the following pairs, and in a sentence explain your answer. (12pts) O (a)
H3C C OH
CH3CH2 OH
O
O
(b)
H3C C OH
F3C C OH
(c)
O Br3C C OH
O F3C C OH
(d)
O C OH
O CH3CClH C OH
CClH2CH2
Org II Exam 2
Page 2
4)
Name the following compounds in IUPAC acceptable terms. (15pts) O Br
C C
H CH3
O
O
Ph H
NH
H CO2H
Org II Exam 2
Page 3
5)
Explain why propanal is more reactive than propanone towards nucleophilic attack. (10pts)
Org II Exam 2
Page 4
6) The following is taken from a forthcoming publication in the Journal of Organic Chemistry, where a bright young chemist is using classic Diazonium salt chemistry to functionalize some fluorinated cyclophanes. However he was distracted by the wrestling on the TV and left some blanks in his report, help him by filling in the missing products or reagents. (15pts) F F F F
F F F F
F F F F
?
F F F F
NO2
NH2
?
?
H2O, H2SO4 heat
F F F F
F F F F +
N2 Cl
-
1) HBF4 CuBr
2) heat
?
?
?
F F F F
F F F F CO2H
Org II Exam 2
Page 5
6) Give the products formed in five of the following reactions. (15pts) (a)
O Ph C Ph
(b)
O Ph C Ph
1) PhMgBr
O Ph C Ph
1)Ph3P, CH3-Br
(c)
H3C NH2
H+
2) H3O+
2) BuLi 3) warm
(d)
(e)
H3C NH2
H3C NH2
excess CH3CH2CH2-Br
O excess H3C C Cl
NH2 (f)
1) excess CH3-Br 2) Ag2O, H2O, heat
Org II Exam 2
Page 6
7) Give reagents for the following oxidations and reductions, bearing in mind the (in)compatibility of some of the functional groups. (9pts) O H3C C
O
O
O
C OH
H3C C
CH2-OH
O
OH H3C CH
O
O H3C C
O
H3C C
C H
O H3C C
O C H
C H
C OH
8) Methylamine has pKb = 3.36 an ammonia has pKb = 4.74. Indicate which is the stronger base, and explain why one is a stronger base than the other. (7pts) Or Write both the mechanisms for the acid and base catalyzed hydration of acetone. (also 7pts)
Org II Exam 2
Page 7
*Bonus question* (up to 4pts) Why are the basicities of methylamine and trimethylamine about same? (use back if necessary).
Org II Exam 2
Page 8
