CH221 ORGANIC CHEMISTRY I QUIZ 4 11 MAY 2008

Time allowed: 80 minutes Attempt all 40 questions by writing answers for each question on the grid answer sheet provided 1. Which of the circled C-H bonds has the lowest bond dissociation energy? 8. What is the reagent for the following reaction?

9.

Which of the following compounds is (are) a tautomer of compound X drawn below?

2.

Determine the product.

3.

Determine the product

A. B. C.

Compound A Compound B Compound C

D. Compounds A and B are both tautomers of compound X. 4. Determine the product. E. Compounds A, B, and C are all tautomers of compound X.

10.

Which method would work the best in carrying out the following conversion?

5.

Determine the product(s). A. (1) HBr; (2) 2 NaNH2 (1) Br2; (2) 2 NaNH2 (1) Br2, H2O; (2) NaNH2 (1) NaNH2

6.

Determine the product.

B. C. E. 11.

D. (1) BH3, THF; (2) H2O2, NaOH; (3) NaNH2

Give the IUPAC name for the following compound. CH3C(CH3)2CH2C CCH2CH(CH2CH2CH3)CH3

7.

Determine the product.

12. Draw a product(s) of the following reaction.

13.

Determine the product. 22. What is the reagent in the reaction below?

14.

Determine the product. 23. Ozonolysis of compound a below would yield which product(s)?

15.

Determine the product.

16.

Determine the product. A. A B. B C

17.

Determine the reagent.

C.

D. D E. Products A and B

24. When a compound A with molecular formula C12H16 is treated 18. Determine the reagent. with excess H2 in the presence of Pd, a compound having molecular formula C12H20 is formed. How many rings and double bonds does compound A possess? 19. Determine the reagent.

A. Compound A has no rings and 5 double bonds. B. C. Compound A has 1 ring and 4 double bonds. Compound A has 2 rings and 3 double bonds.

D. It's impossible to tell how many rings and double bonds are present. E. 20. After ozonolysis and treatment of the ozonide with zinc, compound A was converted to the compound below. What is the structure of compound A? None of the statements are correct.

21.

What is the starting material in the reaction below?

25. The organic starting material undergoes reduction in all of the following reactions except one. In which reaction is the organic substrate not reduced?

30.

What type(s) of molecular motion is (are) observed using infrared spectroscopy?

A. B. C.

Stretching and bending Rotation and excitation Spin flipping

D. Fragmentation 31. The functional group region of an infrared spectrum is

A. 26. Determine the product. B. C.

where the cations appear. >1500 cm-1. <1500 cm-1.

D. >2500 cm-1. 32. Why is the infrared absorption for the stretching motion of internal alkynes rarely observed? 27. Fill the boxes in the following synthesis. A. B. C. They do not form cations. They are too strong. There must be a change in dipole.

D. They don't have hydrogens. 33. Stronger bonds will be found where in the infrared spectrum?

A. B. C.

Higher molecular weight Lower molecular weight Lower wavenumbers

D. Higher wavenumbers 34. Consider the three organic compounds drawn below. Which of the following statements is (are) true about the IR spectra of 28. Rank the following compounds in order of increasing oxidation level (from lowest to highest). compounds A, B, and C?

29. In conventional mass spectrometry, what is being detected? A. B. C. The molecular weight of the compound The molecular formula of the compound The mass of any cationic species A. Compound A shows strong absorptions at 3000 cm-1 and 1700 cm-1. B. Compound B shows strong absorptions at 3000 cm-1 and 2250 cm-1.

D. The mass of any neutral species

C.

Compound C shows strong absorptions at 3000 cm-1 and 3200-3600 cm-1.

C.

Because a small percentage of the compound will have a carbon that is the isotope 13C instead of 12C

D. Statements (Compound A shows strong absorptions at 3000 cm-1 and 1700 cm-1) and (Compound C shows strong absorptions at 300 cm-1 and 3200-3600 cm-1) are true. E. Statements (Compound A shows strong absorptions at 3000 cm-1 and 1700 cm-1), (Compound B shows strong absorptions at 3000 cm-1 and 2250 cm-1), and (Compound C shows strong absorptions at 3000 cm-1 and 3200-3600 cm-1) are all true. 35. Which of the circled C-H bonds absorbs at the highest wave number in the IR spectrum? 39.

D. Because of fragmentation

Examine the IR below and classify the compound.

A. B. C. 36. A compound X shows a molecular ion at 72 in its mass spectrum, and a strong peak at ~1700 cm-1 in its IR spectrum. Which structures are possible for compound X? 40.

Alcohol Aldehyde Amine

D. Ketone E. Acid

Examine the IR below and classify the compound.

37. Draw a structure that is consistent with a compound that displays a molecular ion at 56 and infrared signals at 2250 and 3600-3200 cm-1?

38.

In a typical mass spectrum, a smaller signal is observed at a mass 1 amu higher than the molecular ion peak. Why?

A. B. C.

Alcohol Aldehyde Amine

A. B.

Due to small impurities in the sample Machine error

D. Ketone E. Acid

CH221 QUIZ 4 ANSWER GRID

Name..

Student Number

Br

Br

2HCl

10

11 2,2,7-trimethyl-4-decyne

12

D
13

B
14

15

16

O O
H H3C H3CH2C H CH3
19 K2Cr2O7 H2SO4, H2O / CrO3, H2SO4, H2O

OH

H3C H3CH2C H

CH3 H
20

OH

17 H2, Lindlar catalyst

18

21

22 RCO3H, H2O(OH ,H )
+ -

23

24

25

E
27 A : CH3CH2Br B : CH3CH2CC
-

26

C : Na, NH3

OH

H3CH2C H D:
29 30

H CH3

H3CH2C H

O
31

H CH3
32

28

BDCA
33

C
34

A
35

B
36

C
37

D
38

D
39

A
40

OH

Total
5