Chem 262

Section 001

Exam 1

Name (please print legibly):________________________________ PID #:_________________________________________________ Pledge: I have neither given nor received aid on this quiz. Signature:_______________________________________________ Please answer all questions on a scantron sheet. Hand in ONLY the scantron sheet, with the pledge signed. 1. Which of the following structures, including formal charges, is correct for diazomethane, CH2N2? A) :CH2=N=N:

B)

C)

D)

E)

Answer: D 2. Which of the compounds below have bonds that are predominantly ionic? A) KCl B) CF4 C) NH3 D) both A and B

E) both B and C Answer: A 3. What is the predicted shape, bond angle, and hybridization for +CH3? A) trigonal planar, 120, sp2 B) trigonal planar, 120, sp3 C) trigonal planar, 109.5, sp2 D) trigonal pyramidal, 120, sp2 E) trigonal pyramidal, 109.5, sp2 Answer: A 4. Which of the following molecules has a net dipole moment of zero? A)

B)

C)

D)

E)

Answer: B

5. Which species act as bases in the following reaction?

A) 1 and 2 B) 3 and 4 C) 2 and 4 D) 1 and 3 E) 2 and 3 Answer: C 6. Which of the following is the best description of the mechanism of the reaction between a ketone and an amine to form an imine? a. concerted bimolecular substitution b. nucleophilic addition followed by elimination c. elimination followed by nucleophilic addition d. electrophilic addition followed by rearrangement ANS: b 7. What is the relationship between the following two structures?

a. tautomers b. constitutional isomers, but not tautomers c. resonance structures d. stereoisomers ANS: a 8. What is the relationship between the following two structures?

a. tautomers b. constitutional isomers, but not tautomers c. resonance structures d. stereoisomers

ANS: c 9. What is the major organic product obtained from the following reaction?

a. 1 b. 2 c. 3 d. 4 ANS: d 10. What is the major organic product obtained from the following reaction?

a. 2-pentanone b. (E)-3-penten-2-ol c. 2-pentanol d. 4-hydroxy-2-pentanone ANS: b 11. What is the major organic product obtained from the following sequence of reactions?

a. 1 b. 2 c. 3 d. 4 ANS: a 12. What is the major organic product obtained from the following reaction?

a. 1 b. 2 c. 3 d. 4 ANS: d 13. What is the major organic product obtained from the following sequence of reactions?

a. 1 b. 2 c. 3 d. 4 ANS: c

14. Which ketone-diol undergoes cyclization to form the following ketal?

a. 1 b. 2 c. 3 d. 4 ANS: d 15. What is the major organic product obtained from the following reaction?

a. 1 b. 2 c. 3 d. 4 ANS: a 16. Which of the following is the best description of the overall transformation involved in a Wittig reaction? a. addition b. substitution c. elimination d. rearrangement ANS: b

17. What is the major organic product obtained from the following reaction?

a. 1-butene b. 2-butene c. 2-methylpropene d. 2-methyl-1-propanol ANS: c 18. What is the IUPAC name of the following compound?

a. (S)-3,4,4-trimethylpentanal b. (R)-3,4,4-trimethylpentanal c. (R)-3-tert-butyl-3-methylpropanal d. (R)-3-tert-butylbutanal ANS: b 19. What is the major organic product obtained from the following reaction?

a. 1 b. 2 c. 3 d. 4 ANS: a 20. What is the major organic product obtained from the following reaction?

a. 1 b. 2 c. 3 d. 4 ANS: b 21. Which of the following is not true regarding the carbon atom of the methylene carbene, H2C: ? a. it is sp2 hybridized b. it has a complete octet of valence electrons c. it has a vacant 2p atomic orbital d. it has a lone pair of electrons in an sp2 molecular orbital ANS: b 22. What is the major organic product obtained from the following reaction?

a. (E) 2-iodo-2-butene b. 1-iodo-2-methylpropene c. methylcyclopropane d. (E) 2-butene ANS: d 23. Which of the following alcohols can be prepared from a Grignard reagent and ethylene oxide?

a. only 1 and 2 b. only 1 and 4

c. only 1, 2 and 3 d. only 2 and 4 ANS: d 24. What is the major organic product obtained from the following sequence of reactions?

a. (E) 6,6-dimethyl-1-hexene b. (E) 5,5-dimethyl-1-heptene c. (E) 6,6-dimethyl-1-heptene d. (E) 6,6-dimethyl-2-heptene ANS: d 25. What carbonyl compound and what phosphonium ylide are required for the synthesis of the following alkene?

A) I B) II C) III D) II or III E) I, II, or III Answer: D 26. The color of my exam is: A) white B) blue C) magenta D) chocolate Ans: B