14D f08 E01

Chemistry 14D Fall 2008
Exam 1
Page 1
For any question on this exam worth three or more points, you have two choices: answer the question as written or you may write and circle the phrase one point. If you write one point you will receive one point (and only one point) of credit for the question. One point overrides anything you have written for that question, regardless of its accuracy. Example: (10) Briefly explain everything about organic chemistry. 1.
One point
(2) Circle the letter of the answer that best completes this sentence: In an SN2 reaction, if the carbon that bears the leaving group has R configuration, then in the product the configuration of this same carbon ... (circle one): (a) ...is always S (d) ...is mostly R, rarely S (b) ...is mostly S, rarely R (e) ...is always R (c) ...is sometimes S and sometimes R (f) ...cannot be determined.
2.
(2) The principle cause(s) of inversion in an SN2 reaction are (circle all that apply): (a) steric hindrance (d) p orbital (b) tetrahedral carbon (e) a good nucleophile (c) !* orbital (e) none of these
3.
(2) The principle cause(s) of inversion in an SN1 reaction are (circle all that apply): (a) steric hindrance (d) p orbital (b) tetrahedral carbon (e) a good nucleophile (c) !* orbital (e) none of these
4.
(3) DMF is (circle all that apply): Polar Nonpolar Protic Aprotic An ether CH3CH2SCCl3SAn alcohol CF3CH2OCF3SO3An amide CF3CH2OH
5. 6. 7.
(2) Circle the best nucleophile in DMF: CH3CH2O(2) Circle the best leaving group: CH3SCF3S-
(2) Using the best leaving group from the previous question, illustrate the formation of a carbocation that is 3o with resonance. Include the appropriate curved arrows.
8.
(8) Consider the effect of changing each of the following reaction aspects on the rate of any SN2 or SN1 reaction, when all other reaction aspects remain the same. Write one of the following in each blank: increases, decreases, no change, or cannot determine from information given. (a) When reaction temperature is increased, the reaction rate ________________________________________. (b) When [nucleophile] is increased, the reaction rate ______________________________________________. (c) When energy of activation for one mechanism step is increased, the reaction rate _____________________. (d) When solvent " is increased, the reaction rate _________________________________________________.
9.
(2) Assign the following " values to the solvents shown below: 25, 20, and 11. CH3CH2OH " = __________ (CH3)3COH " = __________ CH3CH2CH2OH " = __________
Exam 1
Page 2
10. (8) Complete the following SN2 reaction mechanism by adding curved arrows, and completing the partial structures.
CH3 C CH2CH3
Na H I
SCH3
I
CH3 C
CH3OH
Questions 11-15 refer to this reaction:

Cl CH3
NaI + CH3OH H3C I H3C OCH3
Product A 11. (2) Circle the major product of this reaction: A B 12. (4) Write two more reasonable (but not necessarily major) products of this reaction.
Product B
13. (2) Which of the following species is present in the reaction and the best nucleophile? Circle one: IClNa+ CH3OH CH3O-
14. (4) Circle poor or good, then complete the statement using fifteen words or less: The principle reason why iodide ion is a poor / good nucleophile is...
15. (4) Circle SN2 or SN1, then complete the statement in fifteen words or less: The principle reason why this reaction occurs by the SN2 / SN1 mechanism is...
16. (2) Circle the letter of the slowest SN2 reaction. (a) CH3I and NaF in DMF (b) CH3I and NaF in CH3OH (c) CH3I and NaCl in DMF (d) CH3I and NaCl in CH3OH
17. (4) Circle the letter of the slowest SN1 reaction, the write the product of this slowest reaction in the space below. (a) (CH3)3CI and NaF in H2O (b) (CH3)3CI and NaCl in H2O Product of slowest reaction: (c) (CH3)3CCl and NaF in CH3OH (d) (CH3)3CCl and NaCl in CH3CH2OH
Exam 1
Page 3
18. (3) Draw the most stable carbocation you can that consists of exactly four carbons, any number of hydrogens, and no additional elements.
CH3
OSO2CF3 HO H2O
CH3
Questions 19 and 20 refer to this reaction:
19. (10) Write the mechanism for the reaction shown above. Unambiguously label each step that involves a carbocation with the name of the carbocation fate it illustrates. If no carbocations are involved, then no labels are necessary.
20. (4) Using any structure drawn in the reaction mechanism in the previous question, illustrate all carbocation fates not included in the mechanism. Include the corresponding curved arrows in this illustration.
CH3
CH2
CH3
CH3
21. (2) Circle the most stable alkene:
22. (2) Complete this drawing to make an alkene that has both cis and E configuration. Your answer can have no atoms with nonzero formal charges, no more than four carbon atoms, but you may use any number of atoms of any other elements. If this is not possible, write not possible.
C C C
Exam 1
Page 4
23. (6) Write a realistic example of an E2 reaction, including all reactants, products, and mechanism. The example may not include any halogen atoms, and must clearly illustrate Zaitsevs Rule. Transition states do not have to be included.
24. (16) For each reaction circle the most likely mechanism, then write the major reaction product in the box. If two or more products are formed in roughly equal amounts, draw all the products.
CH3
(a)
F
I CH3
NaOCH3 CH3OH
S N2
S N1
E2
F NaI
(b)
Cl
acetone
S N2
S N1
E2
(c)
I CH3
CH3OH
S N2
S N1
E2
NH2
(d)
H3C H
I acetone
S N2
S N1
E2
25. (2) Provide concise yet precise definition for leaving group:

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Chemistry 14D Fall 2008

Chemistry 14D Fall 2008

Questions 11-15 refer to this reaction:

NaI + CH3OH H3C I H3C OCH3

Chemistry 14D Fall 2008

Questions 19 and 20 refer to this reaction:

21. (2) Circle the most stable alkene:

Chemistry 14D Fall 2008

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