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Exam 3 Questions | Organic Chemistry I | CHE 230.00, Exams of Organic Chemistry

Illinois State University (ISU)Organic Chemistry

Prof. Richard Nagorski

Exam 3 Material Type: Exam; Professor: Nagorski; Class: Organic Chemistry I; Subject: Chemistry ; University: Illinois State University; Term: Fall 2007;

Typology: Exams

Pre 2010

Uploaded on 09/21/2008

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Organic Chemistry I

Chem 230

Exam 3

April 2nd, 2007

Dr. R.W. Nagorski

The only place where success comes before work is the dictionary.

Vidal Sassoon (1928–)

1) ______/6 9) ______/3

2) ______/4 10) ______/5

3) ______/10 11) ______/7

4) ______/8 12) ______/9

5) ______/6 13) ______/27

6) ______/6

7) ______/4

8) ______/5

Bonus ______/6

Total ______/100

Name:___________________

ID#:_____________________

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Partial preview of the text

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Organic Chemistry I

Chem 230

Exam 3

April 2

nd

Dr. R.W. Nagorski

The only place where success comes before work is the dictionary. Vidal Sassoon (1928–)

1) /6 9) /

2) /4 10) /

3) /10 11) /

4) /8 12) /

5) /6 13) /

6) ______/

7) ______/

8) ______/

Bonus ______/

Total ______/

Name:___________________

ID#:_____________________

Chem 230 Exam 3 Page 2 April 2 nd^ , 2007

Nomenclature:

Give the correct IUPAC names for the following compounds. ( 6 points )
Draw the structures that are represented by the following IUPAC names. ( 4 points )

a)

b)

c)

H

a)

b)

bicyclo[4.4.0]decane

1,1-diethyl-2,2-dimethyl-3,3-dipropylcyclopropane

Chem 230 Exam 3 Page 4 April 2 nd^ , 2007

e) Which of the bases below would be best to accomplish the following reaction?

Conceptual Problems:

For the structures shown below, add the substituents to the chair forms provided and label the methyl groups as axial or equatorial for each structure. (8 points)
Rank the following carbocations from most stable to least stable and provide the two reasons for the ranking provided. ( 6 points )

CH 2 CH 2 CH 2 Br (^) CH 2 CH^ CH 2

a) b) c)

d) e) CH 3 CH 2 O-^ Na +

(CH 3 ) 3 CO-^ Na + CH 3 O -^ Na +^ (CH 3 ) 2 CHO -^ Na +

Na+^ -OH

a)

b)

CH 3

CH 2

Chem 230 Name:_______________________ Page 5 April 2 nd^ , 2007

Rank the following alkenes from most stable to least stable. ( 6 points )
Circle the more stable chair conformer. (4 points)
For the following pairs of reactions, circle the reaction that will occur more quickly. ( 5 points )

a)

b)

CO 2 H

OH HO

HO

OH OH

OH

CO 2 H

OH

H

OCH 3

HOCH 3

a)

O S CH 3

O

O S CF 3

O

I
I

CH 3 OH

I

b)

c) d)

Cl CH 3

NH 3

H 2 N CH 3

HCl
Cl

Br

H 2 O

I

HBr
HBr

NH 2

OH

Br (^) OH

I

H 2 O 10%

H 2 O

acetone 90% (^) HO

HO

+ HI

e)

Chem 230 Name:_______________________ Page 7 April 2nd^ , 2007

For the following reaction, provide a mechanism for the production of the product shown below ( 9 points )

Reactions:

Give the products for the reactions shown below (circle the major product of each reaction if more than one product is obtained). ( 27 points )

H 2 O

Br

CH 3 CH^3

OH

HBr

a)

I

b)

HO

O

H 2 O

S

O

CF 3

Br

Chem 230 Exam 3 Page 8 April 2nd^ , 2007

d)

f)

e)

DMF

g)

c)

h)

I

Cl (^) H

OH

CH 3 CH 2 OH

i) NH 3

LDA

H

C N

Br

EtOEt

H I

Br

OH

Br CH 3 O -

CH 3 OH

Br

Group***Period

(^1) IA1A

(^2) IIA2A

3 IIIB3B

4 IVB4B

(^5) VB5B

6 VIB6B

7 VIIB7B

8 VIII 8

9 VIII 8

(^10) VIII^8

11 IB1B

(^12) IIB2B

(^13) IIIA3A

(^14) IVA4A

(^15) VA5A

(^16) VIA6A

(^17) VIIA7A

18 VIIIA 8A

1

1 H

2

He4.

2

3 Li

4

Be9.

5 B

6 C

7 N

8 O

9 F

10 Ne20.

3

11 Na22.

12

Mg24.

13 Al26.

14 Si28.

15 P30.

16 S32.

17 Cl35.

18 Ar39.

4

19 K39.

20 Ca40.

21 Sc44.

22 Ti47.

23 V50.

24 Cr52.

25

Mn54.

26 Fe55.

27 Co58.

28 Ni58.

29 Cu63.

30 Zn65.

31 Ga69.

32 Ge72.

33 As74.

34 Se78.

35 Br79.

36 Kr83.

5

37 Rb85.

38 Sr

39 Y

40 Zr91.

41 Nb92.

42

Mo95.

43 Tc(98)

44 Ru101.

45 Rh102.

46 Pd106.

47 Ag107.

48 Cd112.

49 In114.

50 Sn118.

51 Sb121.

52 Te127.

53 I 126.

54 Xe131.

6

55 Cs132.

56 Ba137.

57

La*138.

72 Hf178.

73 Ta180.

74 W183.

75 Re186.

76 Os190.

77 Ir190.

78 Pt195.

79 Au197.

80 Hg200.

81 Tl204.

82 Pb207.

83 Bi209.

84 Po(210)

85 At(210)

86 Rn(222)

7

87 Fr(223)

88 Ra(226)

89

Ac**

(227)

104 Rf(257)

105 Db(260)

106 Sg(263)

107 Bh(262)

108 Hs(265)

109 Mt(266)

110

Uun

()

111

Uuu

()

112

Uub

()

113 Uut()

114

Uuq

()

115

Uup

()

116

Uuh

()

117

Uus

()

118

Uuo

()

Exam 3 Questions | Organic Chemistry I | CHE 230.00, Exams of Organic Chemistry

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Download Exam 3 Questions | Organic Chemistry I | CHE 230.00 and more Exams Organic Chemistry in PDF only on Docsity!

Organic Chemistry I

Chem 230

Exam 3

April 2

nd

Dr. R.W. Nagorski

1) ______/6 9) ______/

2) ______/4 10) ______/

3) ______/10 11) ______/

4) ______/8 12) ______/

5) ______/6 13) ______/

6) ______/

7) ______/

8) ______/

Bonus ______/

Total ______/

Name:___________________

ID#:_____________________

H

a)

b)

CH 3

CH 3

CH 2

OCH 3

HOCH 3

O S CH 3

O

O

O S CF 3

O

O

CH 3 OH

CH 3 OH

I

I

NH 3

H 2 N CH 3

H 2 N CH 3

I

OH

I

I

I

H 2 O 10%

H 2 O

HO

+ HI

+ HI

H 2 O

CH 3 CH^3

OH

I

HO

O

H 2 O

S

O

O

CF 3

DMF

I

OH

CH 3 CH 2 OH

LDA

H

C N

H I

OH

Group***Period

1 H

He4.

3 Li

Be9.

5 B

1) /6 9) /

2) /4 10) /

3) /10 11) /

4) /8 12) /

5) /6 13) /