Sp 2011 Final

Organic II

200pts (Weighted as 300)

NAME: If you do not wish to have your graded exam script placed outside my office, then please check this box

1) Identify the class of compounds that the following molecules belong to (12pts).
R C NH2 O R O H R O O R

R C H O

R C R O

R C Cl O

R C O-R O

2) Draw a Lewis structure including lone pairs for the following similar but different species: (12pts)

Nitronium Ion NO2+

Nitrosonium Ion NO+

Nitric Acid HONO2

Nitrous Acid HONO

3) What is an YLID ? (3pts).

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4) Identify each of the below reactions either as a substitution, addition, elimination or condensation. (16pts)

NO2 (a) O (b) R R R CN (c) F (d) OCH3 OH R

CH2OH O (e) R R R

CHO OH R H

O (f) R R R

OH R OH O Cl R OH N-CH3 R R R

(g)

O R O R

(h)

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5) Define the following terms (9pts). CONCERTED REACTION

PERICYCLIC REACTION

THERMODYNAMIC PRODUCT

6) Give two uses of Molecular Orbital theory. (4pts).

7) State whether each of the following Molecular orbitals are overall bonding, antibonding or nonbonding (6pts).

(a)

(b)

(c)

8) Draw two resonance structures for a carboxylate anion RCO2- (4pts).

9) Give two properties of a Protecting Group. (2pts)

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10) Indicate which of the following molecules are aromatic, non-aromatic or anti-aromatic. (Assume all the molecules are planar). (15pts)
H N + H S H3C CO2H

CH3 O +

CH3 Al

11) Circle the more stable species in these pairs. (8pts)

a)

b)

c)

O d)

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12) Give the products formed in five of the following reactions and cross out the transformation you do not wish me to grade. (15pts)
O Ph C CH3

(a)

1)Ph3P, CH3CH2CH2-Br 2) BuLi 3) warm

NH2 (b)

H-F

NH2 (c)

1) excess CH3I 2) Ag2O, H2O, heat

NH2 (d)

excess CH3CH2-I

1) NaCN (e) OTos 2) LiAlH4, H2O

(f)

O H3C C CH3

1) PhCH2MgBr 2) H3O+

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13) The below heterocycle is pyridine, and it is 6 Hckel aromatic.

N

Explain why there are 6 electrons (2pts)

What is the hybridization of the 5 carbons in the ring (2pts)

What is the hybridization of the Nitrogen atom (2pts)

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14) Explain briefly why each of the following attempted reactions are fundamentally flawed, and will not work. (10pts)
Friedal Craft Acylation

NO2 O2N

NO REACTION

KMnO4

NO REACTION

2+2 Thermal Cycloaddition

NO REACTION

Nucleophilic Aromatic Substitution NO REACTION

CF3 CF3

Diels-Alder

NO REACTION

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15) Give reagents to accomplish five of the following transformations, and cross out the transformation you do not wish me to grade. (15pts)
SO3H

Br

O O O

CO2H

O O2N H2N Ph H N

CO2H

CHO

NO2

Cl

O H

O OH

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16) Circle the strongest base in the following threesomes. (10pts)

H N (a) H N CH3 N

(b)

CH3 N CH3

NH2

NH2

(c)

NH2

NH

N O

O (d) N H

O O N H O

H N O

(e)

HCl

H 2O

HF

17) Name the following compounds in IUPAC form (15pts).

Br O O

Cl O O N

O O

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18) Circle the stronger acid in the following pairs. (8pts)

O (a) H3C C OH CH3CH2 OH

(b)

O F3C C OH

O Br3C C OH

CO2H (c) Cl

CO2H Cl Cl

(d)

O HO S OH O

O H C OH

19) What two products are formed when an acid chloride is hydrolyzed by water ?

Write the mechanism for this reaction. (2+4pts)

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20) Give reagents for the following transformations. (8pts)

O O H

OH

OH

Ph N O H H N N

Ph

CF3

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21) Give the mechanism for one of the below conversions. (16pts)
O (a) H3C Ph H2SO4 HOCH2CH2OH

O H3C

O Ph

(b)

NH2

NaNO 2, HCl

+ N N Cl-

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*Bonus question* (up to 4 points) Draw a picture which describes your Organic chemistry experience at Rutgers, Camden.

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