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SPRING 2020 Organic II Final Exam lOOpts (graded as ISOpts)
Name
1) Identify the class of compounds (functional group) each of the following moleculesbelongs to. (IOpts)
II II
o o
© ©NR4 R-CEN R-y=N
r\
VR R O
R-C-R HO OH RO OHii R'^OR R H
2) Circle the molecule (above) whose name means "without water". (Ipt)
3) Explain the following terms. (4x2= 8pts)
(a) Deactivating substituent (for EAS)
(b) Protic Acid
(c) Carboxylic Acid Derivative
(d) Pericyclic reaction
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4) (l+4=5pts) The following compound was produced in a [4+2] cycloaddition (Diels-Alder) reaction.
Ck ̂ ̂CN
a) How many pi (ti) bonds are in this product?
b) Draw the diene and dienophile which would react together to give this product.
5) (3+l=4pts) Draw in the curly arrows to show the formation of these 1,2- and 1,4-addition products.
CI-CI
^
e
ci
^ f
Ci
CI
©:CI
CI
CI
CI
ii) Indicate which product is the thermodynamic product.
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6) Write the mechanism {i.e. curly arrows) for the reaction of a SECONDARY AMINEwith an ACID CHLORIDE to generate an AMIDE. (5pts).
7) i) Write the mechanism (i.e. curly arrows) for the reaction of a ALDEHYDE with aGRIGNARD REAGENT that upon treatment with acidic water produces aSECONDARY ALCOHOL. (4+l=5pts)
ii) What specific class of reaction is the overall transformation of aldehyde —♦ secondaryalcohol? (It has the initials N and A).
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8) Indicate which of the following molecules are aromatic, non-aromatic or anti-aromatic. (Assume all the molecules are planar). (Spts)
QN=\
Br
(J h'®0-^
9) Circle the strongest acid in the following threesomes. (3pts)
(a)
-CH3
CH3 o
CH,
CH3 CH3
COjH
(b)
NH2
CO2H CO2H
CF3
OH
(0 0^°'"
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10) Give the products in all six of the following reactions, paying attention toregio/stereochemistry where applicable. If you believe there Is no reaction. Indicate that.(6x2=12pts)
Ph^C=CH2
pi/
\ //
O H-CEC-H
NHCOCH3
CH2CH3
CH2CH3
mCPBA
NaOH
heat
H30'*", heat
Br2, FeBr3
Br?, UV light
(radical reaction)
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11) Fill in the gaps (SM/reagents/products) for all five of the following transformations.(5x2= I Opts)
(a)I I
^Cl
(c)
(d) O
(e)
1)NaCN2) LiAIH4. H2O
(b) —NO2 ►
o
-C| AICI3
OCH3
o
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12) i) Circle the most basic atom in this molecule. (l+2=3pts),01
N
ii) Explain your answer to 12i).
*BONUS POINT*What (non-lUPAC) trade name is this pharmaceutical commonlycalled?
13) Fill in the gaps (products or reagents) for all five of the following transformations.(5x2=1 Opts)
14) Name the following compounds in lUPAC form (2x3=6pts).
0 0 o
O
01
01
15) Draw in line angle form {stickfigure) the following named molecules. (2x3=6pts)
2-Chiorobutanoyl Chloride 2-Methylpyrrolc
16) Write the mechanism {i.e. curly arrows) for this Electrophilic Aromatic Substitution(EAS reaction) of Benzene that produces Nitrobenzene. (You do not need to draw all theresonance structures of the intermediate sigma complex). (4pts)
©0=N=0
e 9,O-S-OH
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SPRING 2020 Organic II Final Exam lOOpts (graded as ISOpts)
Name
4) (l+4-5pts) The following compound was produced in a [4+2] cycloaddition (Diels-Alder) reaction.
Ck ̂ ..CN •=
Cl' 'CN
a) How many pi (n) bonds are in this product?
b) Draw the diene and dienophih which would react together to give this product.
Cl
Cl
ClJ
cyj
5) (3+l=4pts) Draw in the curly arrows to show the formation of these 1,2- and 1,4-addition products.
Cl
01 Cl
Cl
ii) Indicate which product is the ihermodynamic product.
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6) Write the mechanism {i.e. curly arrows) for the reaction of a SECONDARY AMINEwith an ACID CHLORIDE to generate an AMIDE. (5pts). o
^ /. O ̂ U ' ©
V_y L. HR-
I .'Ci®
0
\l
7) 1) Write tlie mechanism {i.e. curly arrnw.H) for the reaction of a ALDEHYDE with aGRIGNARD REAGENT that upon treatment with acidic water produces aSECONDARY ALCOHOL. (4+l=5pts)^ H
4-u «-t-H H.0k
ii) What specific class of reaction is the overall transformation of aldehyde —» secondaryalcohol? (// has the initials N and A).
0^\ 5 ?/?«/>/Sp20org2final I'age 3
8) Indicate which of the foliowing molecules are aromatic, non-aromatic or anti-aromatic. (Assume all the molecules arc piatiarl. (8pts)
^O'
N
N
H H
®o^
M0^ Kiol
9) Circle the strongest acid in the following threesomes. (3pts)
(a)
o
o'XHa
CH3
CH3
(b)
CO2H
NH2
CO2H
(c)
OH
OH
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10) Give the products in all six of the following reactions, paying attention toix'gio/srereochemisirv where applicable. If you believe there is no reaction, indicate that(6x2=i2pts)
Ph
C=CH2Ph
mCPBA
o
NaOH
o
H-C=C-H
heat
NHCOCH3
H3O*, heat
CH2CH3
Br2, FeBrg6r
fir
CH2CH3
Br2, UV light ^
(radical reaction)
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1 1) Fill in the gaps (SM/reagcnts/products) for all five of the following transformations.(5x2=10pts)
(a)
Cl
1)NaCN2) LiAlH4, H2O
(b) / NO2 // w
(c)
0
-Cl '^"^'3
(d)
CD N)c^,O
(e)
C9
OCH-:
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12) i) Circle the most basic atom in this molecule. (l+2=3pls)XI
HO
X 'ii) Explain your answer to 121). a) |\) tfi,^ O G.
W) fO '\;s SpjC3\Uj \wo o^
14) Name the following compounds in lUPAC form (2x3=6pts).
0 0 o
L ̂ V
v^CI
15) Draw in line angle form {stickfigure) the following named molecules. (2x3=6pts)
2-Chlorobutaiu)yl Cliloride 2-Methylpyrrole
O
e\
c\
16) Write the mechanism {i.e. curly arrows) for this Electrophilic Aromatic Substitution(HAS reaction) of Benzene that produces Nitrobenzene. (You do not need to draw all theresonance structures of the intermediate sigma complex). (4pts)
NO-
© MO-S-OH
I I
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