Sp 2003 Final Organic II Name

200pts (Weighted as 300)

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Good luck, I believe in you, you can do it, etc., and please read the questions! 1) Identify the class of compounds that the following molecules belong to (12pts).
R C H O R C R O R C Cl O R C O-R O

R C NH2 O

R O H

R O O R

2) Draw Lewis structures (lone pairs not required) for the following classes of compound. (12pts)

Primary Amine

Alkyl Azide

Aryl Diazonium Ion

Ether

Carboxylic Acid

Peroxy Acid

Alkyl Nitrile

Isocyanate

3) Circle a molecule in (1) or (2) with an SP hybridized atom. (1.5pts) 4) Put a cross through a compound in (1) or (2) which is relatively unstable and will decompose just above room temperature (1.5pts).

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5) Identify the general class of each of the below reactions (e.g. oxidation, electrophilic addition, etc) (16pts)
HNO3 (a) O (b) R R OH R CN CH3O (c) F PCC (d) OCH3
-

NO2

HCN

CH2OH O (e) R H (f) R OH NaBH4 R

CHO OH R H

H2SO4

(g)

O R O R R Cl

OH

O R OH

(h)

CH3NH2, H+

N-CH3 R R

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6) Define the following terms (10.5pts). CONDENSATION REACTION

PERICYCLIC REACTION

KINETIC PRODUCT

7) Give one use of Molecular Orbital theory, and also state a disadvantage of MO theory. (4pts).

8) State whether each of the following Molecular orbitals are overall bonding, antibonding or nonbonding (4.5pts).

(a)

(b)

(c)

9) Draw two Lewis resonance structures for a carboxylate anion RCO2(4pts).

10) Show (using curly arrows) how they interconvert (2pts).

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11) Indicate which of the following molecules are aromatic, non-aromatic or anti-aromatic. (Assume all the molecules are planar). (15pts)
+ O +

CH3 N

P N Mg-Br N

H H N+

12) Pick one of the above aromatic molecules, and use the polygon rule to demonstrate its aromaticity. (8pts)

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13) Give the products in six of the following reactions, paying attention to regio/stereochemistry where applicable. (18pts)
heat NC CN

Br

OH

1) NaOH 2) CH3CH2I

Ph C CH2 Ph

Br2, H2O

KOH

Excess HI O O

CH3 CO, HCl CuCl, AlCl3 NO2 1) Zn, HCl 2) NaNO2, HCl 3) CuCl, HCl CH3 Br2, uv light

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14) The below heterocycle is pyrrole, and it is 6 Hckel aromatic.

H N

Explain why there are 6 electrons (2pts)

What is the hybridization of the 4 carbons in the ring (1.5pts)

What is the hybridization of the Nitrogen atom (1.5pts) 15) Write the mechanism for the formation of the nitronium ion NO2+ which is the active electrophile in nitration EAS reactions. (8pts)
H O O S O H O H O O N+ O_

NO2+

H2O

HSO4-

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16) Give reagents and conditions to accomplish five of the following transformations. (15pts)

CO2H

CHO

O H

O H

NO2

Br NO2

Cl

O2N CN

O2N

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17) Circle the stronger base in the following pairs, and in a sentence explain your choice. (6pts)
O C H2 C

(a)

F3C N H

CH3

H3C N H

CF3

(b)

NH2

NH2

18) Circle the stronger acid in the following pairs, and in a sentence explain your answer. (12pts)
(a) O H3C C OH CH3CH2 OH

(b)

O HO S OH O

O H C OH

(c)

O Cl3C C OH

O Br3C C OH

CO2H (d) F

CO2H F F

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19) Name the following compounds in IUPAC form (14pts).

O H F (CH3CH2CH2)4N Br
+ -

CH3 CH3 O HO O NH2

20) Fill in the blanks for two of the following reactions. (6pts)
NH2 1) excess CH3-Br (a) 2) Ag2O, H2O, heat O excess H3C C Cl

(b)

CH3CH2 NH2 O H3C C CH3

(c)

1) PhMgBr 2) H3O+

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21) Explain why nucleophilic ring opening of the below epoxide occurs with different regiochemistry in the two examples below. (9pts)

NaOCH3, CH3OH CH3O OH H CH2CH3 H CH2CH3 H CH2CH3 H CH2CH3

H2SO4, CH3OH

HO OCH3 H CH2CH3 H CH2CH3

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22) Give the mechanism for two of the below conversions. (16pts)
NH2 (a) NaNO2, HCl + N N Cl-

O (b) Ph Ph

HOCH2CH2OH H2SO4

O Ph

O Ph

(c)

NH2

1) excess CH3Br 2) Ag2O, H2O, heat

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*Bonus question* (up to 5 points) Name 5 jobs where a good knowledge of organic chemistry is important.

OR

Besides back side attack, name 5 other amusing organic chemistry phrases.

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