2023 F CH202-4-6 - M1 Review Lecture Worksheet

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Toronto Metropolitan University *

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CHEM010

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Chemistry

Date

Jan 9, 2024

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pdf

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12

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Page 1 of 12 1. Nicotine is an addictive substance found in tobacco. Identify (1) the hybridization state and (2) the geometry of each of the two nitrogen atoms in nicotine. 2. Does the following compound have a net dipole moment? 3. Indicate the formal charge on the nitrogen atom in the following Lewis structure: 4. What intermolecular forces are operative between molecules of methanol and water? A. London dispersion forces B. Dipole-dipole forces C. Hydrogen bonding D. All of the above
Page 2 of 12 5. Predict whether vitamin C is water soluble or not. The structure of vitamin C is shown below. 6. All of the following are representations of cis-1,2-dimethylcyclohexane, EXCEPT: A B C D 7. Draw the bond-line structure for vitamin C. 8. How many hydrogen atoms are connected to the carbon atom that bears the negative charge in the structure below?
Page 3 of 12 9. Draw all lone pairs in the following compound (add lone pairs to the following structure): 10. Draw the resonance structure that results from the arrow pushing scheme below: 11. Which of the following has the correct curved arrow(s) placement? A B C D 12. Which of the resonance structures below is least significant or invalid?
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Page 4 of 12 13. Which of the following best represents the resonance hybrid of the given anion? A B C D 14. Consider the nitrogen atoms (labeled A, B and C) in the molecule of vitamin B1 shown below. Which of these nitrogen atoms possess a delocalized lone pair of electrons? A. Nitrogen A B. Nitrogen B C. Nitrogen C D. None of the indicated lone pairs are delocalized
Page 5 of 12 15. Which mechanism below represents the correct curved arrow(s) for a nucleophilic attack? A. B. C. 16. Predict which side of the reaction is favored under equilibrium conditions, and provide a brief explanation. A. Forward direction is favored, because resonance stabilization makes a stronger base than . B. Forward direction is favored, because resonance stabilization makes a weaker base than . C. Reverse direction is favored, because resonance stabilization makes a stronger base than . D. Reverse direction is favored, because resonance stabilization makes a weaker base than .
Page 6 of 12 17. Which of the indicated protons in the given compound is the most acidic? A. Proton A B. Proton B C. Proton C D. Proton D 18. Consider the following acid-base reaction: A. Identify the acid and base between the two reactants. B. Draw the curved arrows showing the reaction. C. Identify the counterion. D. Draw the two products of the proton-transfer reaction.
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Page 7 of 12 19. Give the IUPAC name for the following compound: 20. Which of the following is a constitutional isomer of heptane? A B C D 21. Below are several constitutional isomers with the molecular formula C 6 H 14 . Which of these isomers will have the largest heat of combustion? A B C D 22. Which cycloalkane has the greatest angle strain? A B C D
Page 8 of 12 23. Which of the following conformations of pentane is highest in energy? A B C D 24. Draw the bond-line structure of the compound represented by the Newman projection below: 25. Which conformation of cyclohexane has the most strain? A B C D
Page 9 of 12 26. Which of the following represents the most stable conformation of cis-1,4- dimethylcyclohexane? A B C D 27. Give the IUPAC name for the following compound: A. cis-1,2-Dimethylcyclohexane B. cis-1,6-Dimethylcyclohexane C. trans-1,2-Dimethylcyclohexane D. trans-1,6-Dimethylcyclohexane 28. Identify the relationship between the following compounds: A. identical B. stereoisomers C. constitutional isomers D. compounds with different molecular formulas 29. Identify the relationship between the following compounds: A. identical B. stereoisomers C. constitutional isomers D. compounds with different molecular formulas
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Page 10 of 12 30. Mark all the chiral centers (circle the individual atoms) present in the following structure: 31. Assign the configuration of each chiral center (stereocenter) in the following compound: A. 2R,3R B. 2R,3S C. 2S,3R D. 2S,3S 3-bromo-2-butanol 32. What is the relationship between the following two compounds? A. enantiomers B. diastereomers C. constitutional isomers D. identical compounds 33. What is the relationship between the following two compounds? A. enantiomers B. diastereomers C. constitutional isomers D. identical compounds
Page 11 of 12 34. Identify the configuration of the following alkene: A. (E) B. (Z) C. (cis) D. (trans) 35. For each of the following compounds ( A-C ), identify whether it is compound a) chiral b) meso, or c) achiral but not meso A B C
Page 12 of 12 36. Consider the following S N 2 reaction, and answer questions: A. Draw a complete mechanism. B. Identify the nucleophile and leaving group. Nucleophile: leaving group: 37. For the following multistep (steps A - D ) reaction, read the curved arrows and identify the sequence of arrow-pushing patterns: Step a) loss of leaving group, b) nucleophilic attack, c) proton transfer, or d) rearrangement. A B C D
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