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1. What would be the major product of the following reaction?, Lecture notes of Stereochemistry

A) Enantiomers have identical properties except in chiral environments or with plane-polarized light. B) Reactions involving only achiral or racemic materials ...

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1. What would be the major product of the following reaction?
A)
B)
C)
D)
E)
2. Which of the following would you expect to react fastest with the nucleophile I- (iodide)?
A) CH3CH2CH2Br
B) CH3CH2CH2Cl
C) (CH3)2CHCH2Br
D) (CH3)2CHCH2Cl
E) (CH3)3CCH2Br
3. Which of the following haloalkanes would not undergo the reaction below?
A) (CH3)2CHI
B) CH3Cl
C) (CH3)3CBr
D) CH3CH2Br
E) CH3CH2CH2I
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  1. What would be the major product of the following reaction?

A)

B)

C)

D)

E)

  1. Which of the following would you expect to react fastest with the nucleophile I-^ (iodide)? A) CH 3 CH 2 CH 2 Br B) CH 3 CH 2 CH 2 Cl C) (CH 3 ) 2 CHCH 2 Br D) (CH 3 ) 2 CHCH 2 Cl E) (CH 3 ) 3 CCH 2 Br
  2. Which of the following haloalkanes would not undergo the reaction below?

A) (CH 3 ) 2 CHI

B) CH 3 Cl C) (CH 3 ) 3 CBr D) CH 3 CH 2 Br E) CH 3 CH 2 CH 2 I

  1. Predict the major product of the following reaction:

A)

B)

C)

D)

E) no reaction occurs

  1. What is the major product of the following two-step reaction?

A)

B)

C)

D)

E) No reaction occurs.

  1. Several alkyl halides, including iodomethane, are known carcinogens or cancer-suspect materials. To destroy these materials by conversion to non-electrophilic species, you can react them with nucleophiles. Which of the following would be the best for rapidly destroying methyl iodide (iodomethane)? A) CH 3 OH B) NH (^3) C) H 2 O D) NaI E) CH 3 CO 2 H
  2. Predict the major product of the following reaction:

A)

B)

C)

D)

E) no reaction occurs

  1. Which of the following reagents would best accomplish a typical SN2 reaction? A) CH 3 OH B) H 2 O C) HCN D) KCN E) KO t^ Bu
  1. Which of the following is the best leaving group?

A)

B)

C)

D)

E)

  1. If the reaction rate of the following reaction is x, doubling the concentration of KCN would give what rate?

A) 2x B) x/ C) x^2 D) x^2 / E) No change in reaction rate

  1. What is the correct stereochemistry of the product of the following reaction:

A) 3 R ,4 S

B) 2 S ,3 R

C) 2 R ,3 S

D) 2 R ,3 R

E) 3 R ,4 R

  1. What would be the proper name of the following?

A) (1 R ,2 R )-trans-1,2-cyclohexanediol B) (1 R ,2 S )-trans-1,2-cyclohexanediol C) (1 S ,2 R )-trans-1,2-cyclohexanediol D) (1 S ,2 S )-trans-1,2-cyclohexanediol E) (1 S ,2 R )-cis-1,2-cyclohexanediol

  1. Which of the haloalkanes shown below would react most rapidly with cyanide ion?

A) A

B) B

C) C

D) D

E) E

  1. Which of the following can be used to synthesize ( R )-2-cyanopentane from ( R )-2-bromopentane? A) NaBr B) NaCN C) NaI followed by KCN D) NaCN followed by HI E) This reaction cannot occur
  1. An unknown compound has been isolated in pure form and found to exhibit [α] (^) D = + 15° (c = 4, CH2Cl2). Which of the following might be the structure of the compound?

A)

B)

C)

D)

E)

  1. Which of the following molecules represents a meso compound?

A)

B)

C)

D)

E)

  1. Optically pure ( S )-monosodium glutamate has a specific rotation of + 24°. What specific rotation would ( R )-monosodium glutamate of 50% optical purity have? A) + 24° B) - 24° C) - 18° D) - 12° E) + 18°
  1. Which of the following molecules is not chiral?

A)

B)

C)

D)

E)

  1. How many total stereoisomers of the following are possible?

A) 1

B) 2

C) 3

D) 4

E) 6

  1. Which of the amines below might be appropriate for the resolution of racemic Ibuprofen?

A)

B)

C)

D)

E)

  1. What technique(s) can be used to obtain non-racemic compounds from racemic material? A) Resolution B) Distillation C) Extraction D) Column chromatography E) Both B and C
  1. Which of the following is NOT TRUE for a meso compound: A) It is achiral B) It will rotate plane polarized light C) It may be cyclic or acyclic D) It is a stereoisomer E) It has a mirror plane
  2. How many stereogenic (chiral) centers are found in Rhizoxin?

A) 5

B) 7

C) 9

D) 11

E) 14

  1. The best (most reliable) test for the presence of chirality in a molecule is A) carbon attached to four different groups B) existance of a mirror image C) non-superimposability on mirror image D) two or more isomers possible E) observation of optical rotation in a sample
  2. Which of the following statements is not true? A) Enantiomers have identical properties except in chiral environments or with plane-polarized light. B) Reactions involving only achiral or racemic materials must produce achiral or racemic products. C) Diastereomers have identical properties in all environments. D) Enantiomers exhibit equal and opposite optical rotations. E) All of the above are true.
  1. A particular reaction produces the following two alcohols in a ratio of 95 : 5.

The enantiomeric excess (% ee) is: A) 100 B) 95 C) 90 D) 85 E) none of these

Answer Key - Ferret:Exam:quiz3.qf.ef

  1. C
  2. A
  3. C
  4. B
  5. C
  6. E
  7. A
  8. B
  9. B
  10. E
  11. D
  12. A
  13. A
  14. C
  15. E
  16. D
  17. D
  18. A
  19. B
  20. C
  21. A
  22. C
  23. C
  24. D
  25. D
  26. A
  27. C
  28. E
  29. A
  30. B
  31. D
  32. C
  33. C
  34. E
  35. C
  36. C