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Chem 3361, organic chem 1, Exam III 2019, Kennesaw state university, Animesh Aditya, Exams of Organic Chemistry

Kennesaw State University (KSU)Organic Chemistry

It is solved past EXAM III of Chem 3361, Organic Chemistry 1, Exam III 2019, Kennesaw State University. Prof. Animesh Aditya. It includes topics like substitution and elimination reactions.

Typology: Exams

2018/2019

Available from 06/04/2025

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CHEM 3361-02 Exam III Spring 2019 108 Pts Total Name ____________________________________
Record the following number on your Scantron bubble-sheet by your name __________
Part I. Multiple Choice (90pts, 4.5pts/ea)
For Problems 1&2,
consider the
following reaction.
1. Which of the following is the nucleophile?
2. What is the best description of the attachment of the leaving group?
A. methyl B. 1 C. 2 D. 3º
3. What is the order, most to least, of nucleophilicity of the following in a protic solvent?
I. CH3SH II. CH3S- III. CH3OH
a. I>II>III b. II>III>I c. II>I>III d. III>I>II e. III>II>I
4. What is the order, most to least, of nucleophilicity of the following in an aprotic solvent?
I. OH- II. SH- III. Cl-
a. I>II>III b. I>III>II c. II>III>I d. III>I>II e. III>II>I
For Problems 5&6, consider the following structures.
5. Which of the above represents the most stable cation?
A. I B. II C. III D. IV
6. Which of the above would undergo a hydride shift to form a more stable cation?
A. I B. II C. III D. IV E. more than one of the above
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CHEM 3361 - 02 Exam III Spring 201 9 108 Pts Total Name ____________________________________ Record the following number on your Scantron bubble-sheet by your name __________ Part I. Multiple Choice ( 90 pts, 4.5pts/ea) For Problems 1& 2 , consider the following reaction.

  1. Which of the following is the nucleophile?
  2. What is the best description of the attachment of the leaving group? A. methyl B. 1 C. 2 D. 3º
  3. What is the order, most to least, of nucleophilicity of the following in a protic solvent? I. CH 3 SH II. CH 3 S-^ III. CH 3 OH a. I>II>III b. II>III>I c. II>I>III d. III>I>II e. III>II>I
  4. What is the order, most to least, of nucleophilicity of the following in an aprotic solvent? I. OH-^ II. SH-^ III. Cl- a. I>II>III b. I>III>II c. II>III>I d. III>I>II e. III>II>I

For Problems 5&6, consider the following structures.

  1. Which of the above represents the most stable cation? A. I B. II C. III D. IV
  2. Which of the above would undergo a hydride shift to form a more stable cation? A. I B. II C. III D. IV E. more than one of the above

For Problems 7&8, consider the following structures.

  1. Which of the above gives the fastest SN2 reaction? A. I B. II C. III D. IV
  2. Which of the above gives the fastest SN1 reaction? A. I B. II C. III D. IV
  3. Which of the following conditions would give the most E2 elimination? For Problems 10 and 11 , consider the following reaction.
  4. What would be the effect on the rate of the above reaction of doubling ONLY the concentration of methane thiolate (CH 3 S-)? A. no effect B. the rate will double C. the rate will quadruple D. the rate will triple
  5. Which of the following would increase the rate of the above reaction? I. Increase the concentration of alkyl bromide. II. Change the solvent to DMF (shown at right). A. I only B. II only C. Both I and II D. Neither I or II

CH 3 CHCHCH 3 CH 3 Br (^) KOC(CH 3 ) 3 HOC(CH 3 ) 3 CH 3 CHCHCH 3 CH 3 OC(CH 3 ) 3 CH 3 C=CHCH 3 CH 3 CH 3 CHCH=CH 2 A. B. (^) C. (^) D. CH 3 E. CH 3 CHCHCH 3 CH (^3) OK CH 3 CCH 2 CH 3 CH 3 OC(CH 3 ) 3

  1. What is the compound results from the reaction of the product of the last reaction with CH 3 Br? CHCHCH 3 H 3 C H 3 C OH H 2 SO 4 heat CHCHCH 3 H 3 C H 3 C OSO 3 H CCH 2 CH 3 H 3 C H 3 C OSO 3 H CHCH 2 CH 2 H 3 C H 3 C OSO 3 H C=CHCH 3 H 3 C H 3 C CHCH=CH 2 H 3 C A. B.^ C.^ D.^ H^3 C E. Br (^) KOCH 3 HOCH 3 OH OCH 3 OH A. (^) B. C. (^) D. E.

Part II. Short Answer

  1. Show the curly-arrow mechanism for the formation of the Sn2 product from the following

reaction. Clearly show the expected stereochemistry of the product. Note that potassium

methoxide is ionic; K+^ is a spectator ion and need not be shown. ( 4 pts)

  1. Show the curly-arrow mechanism for the formation of the Sn1 product from the following

reaction. Clearly show the expected stereochemistry of the product. ( 6 pts)

Continued on next page.

Continued on next page.

2. Show the E2 reactions of the following compound, one for the loss of the beta-hydrogen

AND one for the loss of the beta-deuterium. Clearly show the conformations required for

elimination. Ignoring isotope effects, which product is favored and why?

trans alkene is more stable.

If we ignore the isotope effects, then we can say that trans product will be favored over cis product, as

Continued on next page.

3. Identify which of the following is the major product of the following dehydration reaction

and show a curly arrow E1 mechanism to that product. You may represent the acid as simply

“H-A” in the protonation step and the base as “:A-” in the deprotonation step.