1.1 Is the following molecule aromatic or not aromatic? Give reasons for your answer.

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1 Page 1 QUESTION ONE 1.1 Is the following molecule aromatic or not aromatic? Give reasons for your answer. 1.2 List four criteria which compounds must meet in order to be considered aromatic.

2 Page 2 QUESTION ONE (Continued) 1.3 Which of the following statements regarding cyclopentadienyl anion is not correct? H Cyclopentadienyl anion A) It is aromatic. B) It is not aromatic. C) It obeys Huckel s rule. D) It has a closed shell of 6 pi-electrons. 1.4 Which of the following is not a correct statement about the electrophilic substitution mechanism of benzene? A) Benzene functions like a nucleophile. B) Formation of a carbocation intermediate is the rate-determining step. C) The carbocation intermediate contains an sp 3 hybridized carbon in the ring. D) The addition product is a frequent minor product. E) Aromaticity is re-gained by a loss of H +. [6]

3 Page 3 QUESTION TWO 2.1 Which of the following compounds is an amide? 2.2 What is the hybridization and geometry of the carbonyl carbon in carboxylic acids and their derivatives? A) sp 3, tetrahedral B) sp 2, trigonal planar C) sp 2, tetrahedral D) sp 3, trigonal planar E) sp, trigonal planar 2.2 Provide the structure for ethyl-3-methoxypentanoate. (1.5)

4 Page 4 QUESTION TWO (Continued) 2.3 In nucleophilic acyl substitution, which of the following statements is correct? (1.5) A) protonation of the carbonyl is followed immediately by loss of the leaving group. B) loss of the leaving group is followed by rearrangement of the carbocation. C) addition to the carbonyl by a nucleophile is followed by loss of the leaving group D) ester hydrolysis is followed by deprotonation E) an S N 2 reaction occurs 2.4 Complete each of the following reactions: (4) O a) H 3 C Cl + H 3 C O O b) O O H 3 C O CH 3 + OH CO 2 H c) O CH 3 CH 2 C OCH 2 CH 3 + NH 3 d) CH 3 COH + CH 3 OH O (excess) H +

5 Page 5 QUESTION TWO (Continued) 2.5 Which of the following compounds is an aldehyde? 2.6 Would you expect the carbonyl carbon of benzaldehyde to be more or less electrophilic than that of acetaldehyde? Explain using resonance structures.

6 Page 6 QUESTION TWO (Continued) 2.7 Provide the major organic product(s) of the following reaction. 2.8 What class of organic compounds results when cyclopentanone reacts with ethylamine in the presence of trace acid? A) semicarbazone B) semicarbazone C) imine D) enamine E) oxime 2.9 What is the major organic product of the following reaction? [15]

7 Page 7 QUESTION THREE 3.1 Propose a mechanism for the following oxidation reaction known as the Baeyer-Villiger Oxidation: (3) 3.2 Draw the major organic product generated in the reaction below. Pay particular attention to regio- and stereochemical detail.

8 Page 8 QUESTION THREE (Continued ) 3.3 Provide the structure of the major organic product of the following reaction sequence. 3.4 Provide the major organic products of the following. (3) [10]

9 Page 9 QUESTION FOUR 4.1 Which of the following molecular changes is necessary for mass spectrometry to occur? A) excitation of an electron from the ground state to higher energy state. B) change of alignment of an electron in a magnetic field. C) change of alignment of a proton in a magnetic field. D) loss of an electron. E) molecular vibration. 4.2 Which of the following statements best explains the information we can gain from mass spectrometry? A) It allows us to determine the number of protons in a compound. B) It allows us to determine the kinds of functional groups in a compound. C) It allows us to determine the molecular weight and the mass of some fragments of a compound. D) It allows us to determine the presence and nature of a carbocation in the compound. E) It allows us to determine the presence and nature of a free radical in the compound.

10 Page 10 QUESTION FOUR (Continued) 4.3 Predict the molecular formula of the compound represented below based on the MS data given. A) C6H12 m/z Intensity B) C5H24 C) C4H6O2 D) C3H8O2 E) C5H8O 4.4 Which of the following normally occurs in a molecule when a photon of infrared light is absorbed? A) An electron moves to an orbital of higher potential energy. B) The vibration energy increases. C) An electron changes alignment in a magnetic field. D) The molecule gains an electron. E) The molecule loses an electron.

11 Page 11 QUESTION FOUR (Continued) 4.5 Which molecule below has a significant band in the IR at 3400 cm-1 (strong and broad). A) CH 3 CH 2 CH 2 OH B) CH 3 C CCH 2 CH 3 C) CH 3 CH 2 CH(NH 2 )CH 3 D) CH 3 ) 3 N E) CH 3 CO 2 CH 2 CH How could IR spectroscopy be used to distinguish between the following pair of compounds? (i) (CH3)3N and (ii) CH3NHCH2CH3 4.7 In the UV-visible spectrum of (E)-1,3,5-hexatriene, the lowest energy absorption corresponds to: A) a π to π* transition B) a σ to π* transition C) a π to σ* transition D) a σ to σ* transition E) a σ to π transition

12 Page 12 QUESTION FOUR (Continued) 4.8 Which of the following compounds exhibits the highest λmax in UV spectra? Give a brief explanation. 4.9 Which of the following radiation is used in nuclear magnetic resonance spectroscopy? A) X-ray B) Infrared C) Visible D) Radio E) Ultraviolet 4.10 How many signals would you expect to see in the 1H NMR spectrum of the following compounds? a) b)

13 Page 13 QUESTION FOUR (Continued) 4.11 Which of the following methyl groups in compounds I to V below will exhibit the most downfield (highest) chemical shift in 1H NMR spectroscopy? [15]

14 Page 14 QUESTION FIVE 5.1 List the two major classes of synthetic polymers. 5.2 What is the structure of the monomer from which the following polymer is made?

15 Page 15 QUESTION FIVE (Continued) 5.3 Chain-growth polymerization proceeds by which of the following mechanisms? A) radical polymerization B) cationic polymerization C) anionic polymerization D) A and B E) A, B, and C 5.4 What is the difference between natural rubber and Gutta-percha rubber? [4] END

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