Sp 2012 Final Organic II Name

200pts (Weighted as 300)

If you do not want your graded exam placed outside my office, then please check here___

1) Identify the class of compounds that the following molecules belong to (30pts).

2) Draw Lewis structures (lone pairs are required) for the 4 Nitrogen containing species in the bottom line of Question (1). (12pts)

Sp12org2final.docx

Page 1

(3-12) Are True/False (20pts). 3) Aromaticity is a term used to describe very stable bonding in certain special molecules. 4) Hoffman elimination reactions utilize a sterically demanding leaving group. 5) The following ammonium ion is ACHIRAL because of Nitrogen inversion.

6) Conjugation involves the sideways overlap of 3 or more adjacent and aligned p orbitals. 7) For the dissociation constant of acid HA,

8) An isocyanate has the generic formula of RNCO 9) Three membered rings with one Nitrogen are called Aziridines. 10) In MO theory, the symbol * means antibonding. 11) Wittig chemistry involves the reactions of aryl-diazonium salts with Copper (I) salts. 12) For ethene, the LUMO is 2*

Sp12org2final.docx

Page 2

13) Draw in the curly arrows that interconvert one resonance form into the next. (6pts)

14) Draw a carbocation that would be stable in aqueous solution. (3pts)

15) Give reagents for the following multistep transformations. (8pts)

Sp12org2final.docx

Page 3

16) (16pts) For each pair of reactions (a-d), one reaction works better than the other. Indicate which one works best, and write a single sentence to explain why.

Sp12org2final.docx

Page 4

17) (16pts) For each pair of reactions (a-d), one reaction works better than the other. Indicate which one works best, and write a single sentence to explain why.

Sp12org2final.docx

Page 5

18) Indicate which of the following molecules are aromatic, non-aromatic or anti-aromatic. (Assume all the molecules are planar). (20pts)

19) Pick one of the above aromatic molecules, and use the polygon rule to demonstrate its aromaticity. (6pts)

Sp12org2final.docx

Page 6

20) Give reagents to accomplish FIVE of the following six transformations. (Please cross out the one you are not answering). (15pts)

Sp12org2final.docx

Page 7

21) Circle the strongest base in the following threesomes. (12pts)

(a) CH3NH2 H2O NH3

N (b) N H N CH3

(c)

NH2

NH

(d)

NH2

NH2

NH2

(e) O

N H

H N O H N CH3 N O

O N H

(f)

22) Circle the strongest acid in the following threesomes. (6pts)

F CO2H (a) O O Cl F CO2H Cl O Cl CO2H Cl

(b)

CH3CH2-O-O-H

CH3 CO2H

CH3CH2-O-H

(c)

CH3CO2H

H 2O

H2SO4

Sp12org2final.docx

Page 8

23) Name the following compounds in IUPAC form (12pts).

O HO NH2 Br O O

CH3 CH3 O F O O

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

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

Sp12org2final.docx

Page 9

25) Draw in all the curly arrows for the following acid catalyzed hydrolysis of an ester. (12pts)

Sp12org2final.docx

Page 10

*Bonus questions from multiple choice standardized tests* (2+2pts)

Sp12org2final.docx

Page 11