R-C-R HO OH RO OH ii R'^OR R H - Rutgers Universityalroche/sp20org2final.pdfO H-CEC-H NHCOCH3 CH2CH3 CH2CH3 mCPBA NaOH heat H30'*", heat Br2, FeBr3 Br?, UV light (radical reaction)

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

Sp20org2final Page I

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.

Sp20org2fwat Page 2

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).

Sp20org2fmat Page 3

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^°'"

Sp20org2fmat Page 4

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)

Sp20org2final Page 5

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

Sp20org2Jinal Page 6

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


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.

Sp20org2fiiuit Page 2

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

Sp20org2Jintil Page 4

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)

Sp20org2Jliial Page 5

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-:

Sp20org2Jlnal Page 6

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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R-C-R HO OH RO OH ii R'^OR R H - Rutgers Universityalroche/sp20org2final.pdfO H-CEC-H NHCOCH3 CH2CH3 CH2CH3 mCPBA NaOH heat H30'*", heat Br2, FeBr3 Br?, UV light (radical reaction)