Organic II Exam #3
Ch 20-21
(100 points).
NAME:
1)
Name the general class of organic compounds that each of these
molecules belong to, and for the amides indicate whether they are
primary, secondary or tertiary. (13pts)
R
N
O
R C F
R C R
O
R C NR2
O
R C O-R
R C N
O
O
R C O C R
O
R C NH2
O
R C OH
O
O
NH
O
Org II Exam 3
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2)
Circle the stronger acid in the following pairs, and in a sentence
explain your choice. (6pts)
CO2H
(a)
(b)
3)
(a)
(b)
CFH2CH2 CO2H
CO2H
CH3CClH CO2H
Circle the stronger base in the following pairs, and in a sentence
explain your choice. (9pts)
CH3CH2 NH2
H
H3C C N C CH3
O
(c)
O2N
CH3
H
H3C C N CH
3
O
CH3CH2 NH2
O
NH C CH3
O
CH3 C N
Org II Exam 3
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4) Name the following compounds in IUPAC acceptable terms. (20pts)
O
F
O
O
O
O
O
NH
NH2
O
OH
H2N
O
Org II Exam 3
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5) Fill in all the missing products or reagents, and draw the mechanism for
one of the reactions below. (16pts)
O
C
OH
Ph C
CH2CH3
CH3CH2
O
Ph C Cl
O
Ph C O
O
C
Org II Exam 3
CH3CH2OH
CH3
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6) Fill in all the missing products or reagents, and draw the mechanism for
one of the reactions below. (16pts)
H2O
H2SO4
heat
POCl3
Br2, KOH
O
Ph C NH2
H2
C
NH2
Ph
Org II Exam 3
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6) Give the products for the following transformations.(8pts)
O
O
C
O
C
C
O
NH3, H3O+
O
NH3, H3O+
7) Draw the mechanism for one of the above reactions, and indicate which
reaction you would predict to occur the quickest. (12pts)
Org II Exam 3
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*Bonus question* (up to 4pts)
Write the mechanism for the below Curtius rearrangement, that involves the
conversion of an acid chloride to an isocyanate. (Hint: its mechanistically
identical to the Hofmann rearrangement).
O
R C Cl
O
_ + N
R C N N
Org II Exam 3
R N C O
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