Spring 2001 Org II Exam 2 Ch 18-19 100 points 1) Name the general ...
Spring 2001 Org II Exam 2 Ch 18-19
100 points
NAME: If you do not wish to have your script placed outside my office, then please check this box
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) CH2 R C R
O R C R
O R C F
O R C H
2) Name the general class of organic molecules that each of these molecules belong to, and draw the Lewis structure including lone pairs for the following molecules. (10.5pts) CH3CONH2
CH3CN
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CH3NCO
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3) Circle the stronger base in the following pairs, and in a sentence explain your choice. (10pts)
H N
N
(a)
(b)
H2N
H2N
(c)
CH3CH2 CN N
(d)
(e)
H3C
C H2
H N CH3
H3C
C
H N CH3
O
HN
HN N
N+ CH3
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4) Name the following compounds in IUPAC acceptable terms. (12pts)
N H O
Cl
O Cl
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O C
H
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5) Explain why in both pairs, the left hand molecule is more reactive toward nucleophilic attack. (10pts) CCl3
CH3
CH3
CH3 O
O
Ph Ph Ph
Ph O
Ph
Ph Ph O Ph
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6) Compound A is an illegal drug which creates states of entactogenesis and empathogenesis in users. Side effects have been shown to include lowered brain serotonin levels, which results in long term depression and memory degradation. The enantiomer shown is far more active than its mirror image. H H
N
O
H H
H CH3
H CH3
O
HO
O
HO
CH3
A
D
H H
H H
O
N
O
CH3
CH3
HO
N
HO
CH3
CH3
C
B
(i)
Indicate the chiral atom in A, and assign either R or S (2pts)
(ii)
what functional group is attached to the left hand side of the aromatic ring in A? (2pts)
(iii)
What reagents are required to afford D → C? (3pts)
(iv)
What reagents are required to afford C →B? (3pts)
(v)
What reagents are required to afford B→A? (3pts)
(vi)
Draw the mechanism for any ONE of the above reactions (5pts)
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7) Give the products formed in five of the following reactions. (15pts)
(a)
O H3C C CH3
1) PhMgBr 2) H3O+
KCN
(b)
OTos
NH2
(c)
NH2 (d)
NH2 (e)
excess
A
LiAlH4, H2O
O Ph C Cl
excess CH3CH2CH2-Br
1) excess CH3-Br 2) Ag2O, H2O, heat
(f)
O Ph C CH3
1)Ph3P, CH3CH2-Br 2) BuLi 3) warm
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8) Give reagents for the following transformations, bearing in mind the incompatibility of some of the functional groups. (9pts)
H O
O
OH
O
O
O
H O
O
OH
O
O
O
O
H O
O
H
O
OH
OH
O
9) Write both mechanisms for the acid and base catalyzed hydration of propanone (acetone) (8.5pts)
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*Bonus questions* (up to 3pts) Write the mechanism for the reaction of aniline with nitrous acid to generate a diazonium salt. Or Write the (correct) mechanism for the Canizarro reaction.
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100 points
NAME: If you do not wish to have your script placed outside my office, then please check this box
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) CH2 R C R
O R C R
O R C F
O R C H
2) Name the general class of organic molecules that each of these molecules belong to, and draw the Lewis structure including lone pairs for the following molecules. (10.5pts) CH3CONH2
CH3CN
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CH3NCO
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3) Circle the stronger base in the following pairs, and in a sentence explain your choice. (10pts)
H N
N
(a)
(b)
H2N
H2N
(c)
CH3CH2 CN N
(d)
(e)
H3C
C H2
H N CH3
H3C
C
H N CH3
O
HN
HN N
N+ CH3
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4) Name the following compounds in IUPAC acceptable terms. (12pts)
N H O
Cl
O Cl
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O C
H
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5) Explain why in both pairs, the left hand molecule is more reactive toward nucleophilic attack. (10pts) CCl3
CH3
CH3
CH3 O
O
Ph Ph Ph
Ph O
Ph
Ph Ph O Ph
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6) Compound A is an illegal drug which creates states of entactogenesis and empathogenesis in users. Side effects have been shown to include lowered brain serotonin levels, which results in long term depression and memory degradation. The enantiomer shown is far more active than its mirror image. H H
N
O
H H
H CH3
H CH3
O
HO
O
HO
CH3
A
D
H H
H H
O
N
O
CH3
CH3
HO
N
HO
CH3
CH3
C
B
(i)
Indicate the chiral atom in A, and assign either R or S (2pts)
(ii)
what functional group is attached to the left hand side of the aromatic ring in A? (2pts)
(iii)
What reagents are required to afford D → C? (3pts)
(iv)
What reagents are required to afford C →B? (3pts)
(v)
What reagents are required to afford B→A? (3pts)
(vi)
Draw the mechanism for any ONE of the above reactions (5pts)
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7) Give the products formed in five of the following reactions. (15pts)
(a)
O H3C C CH3
1) PhMgBr 2) H3O+
KCN
(b)
OTos
NH2
(c)
NH2 (d)
NH2 (e)
excess
A
LiAlH4, H2O
O Ph C Cl
excess CH3CH2CH2-Br
1) excess CH3-Br 2) Ag2O, H2O, heat
(f)
O Ph C CH3
1)Ph3P, CH3CH2-Br 2) BuLi 3) warm
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8) Give reagents for the following transformations, bearing in mind the incompatibility of some of the functional groups. (9pts)
H O
O
OH
O
O
O
H O
O
OH
O
O
O
O
H O
O
H
O
OH
OH
O
9) Write both mechanisms for the acid and base catalyzed hydration of propanone (acetone) (8.5pts)
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*Bonus questions* (up to 3pts) Write the mechanism for the reaction of aniline with nitrous acid to generate a diazonium salt. Or Write the (correct) mechanism for the Canizarro reaction.
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