Final Review Questions

CHM292 PRACTICE PROBLEMS April 30, 2014 1. Use all the spectroscopic information shown below to assign a structure to your unknown compound. Molecular formula: C9H12 IR spectrum: 1
H NMR spectrum: 13
C NMR spectrum: Mass spectrum: 2. Use all the spectroscopic information shown below to assign a structure to your unknown compound. Molecular formula: C6H10 IR spectrum: 1
H NMR spectrum: 13
C NMR spectrum: Mass spectrum: 3. Use all the spectroscopic information shown below to assign a structure to your unknown compound. Molecular formula: C8H6O2 IR spectrum: 1
H NMR spectrum: 13
C NMR spectrum: Mass spectrum: 4. Use all the spectroscopic information shown below to assign a structure to your unknown compound. Molecular formula: C6H6O2 IR spectrum: 1
H NMR spectrum: 13
C NMR spectrum: Mass spectrum: 5. Use all the spectroscopic information shown below to assign a structure to your unknown compound. Molecular formula: C5H12O2 IR spectrum: 1
H NMR spectrum: 13
C NMR spectrum: Mass spectrum: 6. Use all the spectroscopic information shown below to assign a structure to your unknown compound. Molecular formula: C6H11O2Br IR spectrum: 1
H NMR spectrum: 13
C NMR spectrum: Mass spectrum: 7. Draw the products of the following reactions: 8. Provide a detailed, stepwise mechanism for the reaction shown below: 9. Consider the reaction of (CH3)3CO with iodomethane. Will the reaction rate increase, decrease, or remain the same if the concentration of iodomethane is increased? Explain. ‐
10. Which of the following compounds will undergo an SN2 reaction most readily? A. (CH3)3CCH2I B. (CH3)3CCl C. (CH3)2CHI D. (CH3)2CHCH2CH2CH2I E. (CH3)2CHCH2CH2CH2Cl 11. What is the major organic product in the following reaction? 12. Which of the following alkyl bromides will undergo the SN2 reaction the fastest? 13. What is the major product of the following reaction? 14. Which of the following alkyl halides will react most quickly in an E1 reaction? 15. Predict the major product for each of the following reactions: 16. For each of the following reactions, draw the major product (include appropriate stereochemistry): 17. Draw the major elimination product for each of the following reactions: 18. Fill in the structure of the missing starting materials. 19. Draw the major product for each of the following reactions: 20. Draw the major product for each of the following reactions: H
N
H
a.
H+
O
O
NH3
b.
O
CH3NH2, H+
c.
O
N
H
d.
H+
21. Draw the aldol reaction products for each of the following reactions. O
a.
NaOEt, EtOH
H
O
b.
Ph
NaOEt, EtOH
H
O
c.
NaOEt, EtOH
O
H
d.
O
NaOEt, EtOH

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