Spring 2004 Org II E2
Ch 18-19
100 points
NAME:
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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. (7pts)
O
R C R
CH2
R C R
N-R
R C H
O
R C Cl
2) Draw a Lewis structure including lone pairs for a molecule of the
following general classes: (10.5pts)
Alkyl Diazonium Salt
Ketone hydrate
Isocyanate
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3) Circle the stronger base in the following pairs, and in a sentence explain
your choice. (10pts)
(a)
CH3-NH2
NH3
O
HN
O
HN
CH3
CH3
(b)
(c)
NH3
+
NH4
H3C NH
(d)
CH3
N
(e)
NH3
H2O
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4) Name the following compounds in IUPAC acceptable terms. (12pts)
O
O
F
Br
NH2
O
C
H
5) Explain why in both pairs, the left hand molecule is more reactive toward
nucleophilic attack. (10pts)
H
CH2F
H
O
CH3
O
Ph Ph
Ph
Ph
O
Ph
Ph
Ph O Ph
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6) The reaction of 2-butanone with NaBH4 (sodium borohydride) followed
by addition of acid yields a chiral product.
(i)
Draw the product(s) (2pts)
(ii)
what class of organic compound is the product? (2pts)
(iii)
what is the name of the general class of this reaction? (2pts)
(iv)
is the product mixture optically active or racemic? Explain your
choice. (4pts)
(v)
Draw the mechanism for this reaction (8pts)
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7) Give the products formed in five of the following reactions. (15pts)
O
(a)
1) PhCH2MgBr
H3C C CH3
NH2
2) H3O+
excess CH3CH2CH2-Br
(b)
(c)
(d)
NH2
excess
O
H3C C H
O
Ph C Cl
1)Ph3P, CH3CH2-Br
2) BuLi
3) warm
NH2
1) excess CH3I
(e)
2) Ag2O, H2O, heat
KCN
(f)
OTos
A
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LiAlH4, H2O
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8) Give reagents for the following transformations. (9pts)
O
OH
OH
O
O
O
H
H
OH
OH
OH
9) Write the mechanism for the acid catalyzed hydration of propanone
(acetone) (8.5pts)
*Bonus question* (up to 3pts)
Write the mechanism for the reaction of aniline with nitrous acid to generate
a diazonium salt.
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