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).

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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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