Download AlCl3 heat HCl

Chemistry 231 Summer 2015 July 27, 2015 Name_______________________________ Exam 4 1. (1 point) Spell your name correctly for 1 point. If you miss this question, you deserve to fail the exam. 2. (3 points) Write the mechanism of the following reaction. AlCl3
HCl
heat
Page 1 of 10 Chemistry 231 Summer 2015 July 27, 2015 Name_______________________________ Exam 4 3. (3 points) What would be the product of the reaction of benzene in a Friedel‐Crafts alkylation reaction using CH3CH2Cl? Explain. 4. (3 points) Give the product of the following reaction. H2CrO4
5. (3 points) Name the following: 6. (3 points) List the following compounds in order of decreasing reactivity toward electrophilic aromatic substitution. Explain. a.
Benzene b.
phenol c.
toluene d.
nitrobenzene e.
bromobenzene Page 2 of 10 Chemistry 231 Summer 2015 July 27, 2015 Name_______________________________ Exam 4 7. (3 points) What products would result from nitration of each of the following? Explain your answer. a. Bromobenzene b. benzoic acid 8. (3 points) Give the product of the following reaction. H2
Pd/C
9. (3 points) What product would result from the SN2 reaction of a. 2‐bromobutane and hydroxide ion. Explain. b. 3‐iodopentane and hydroxide ion. Explain. Page 3 of 10 Chemistry 231 Summer 2015 July 27, 2015 Name_______________________________ Exam 4 10. (3 points) For each of the following pairs of SN2 reactions, indicate which reaction occurs faster. Explain. or
or
11. (3 points) How many stereoisomers would be obtained from the following SN1 reactions? Explain. 3
3
12. (3 points) Arrange the following alkyl halides in order of decreasing reactivity in an SN1 reaction. Explain. 2‐bromopentane, 2‐chloropentane, 1‐chloropentane, 3‐bromo‐3‐methylpentane. Page 4 of 10 Chemistry 231 Summer 2015 July 27, 2015 Name_______________________________ Exam 4 13. (3 points) Which alkyl halide in each of the pairs of the following pairs of compounds reacts faster in an SN1 reaction? Explain. or
or
14. (3 points) For the following pair of compounds, or
a. Which alkyl halide would be expected to react faster in an E2 reaction? Explain b. Which alkyl halide would be expected to react faster in an E1 reaction? Explain. Page 5 of 10 Chemistry 231 Summer 2015 July 27, 2015 Name_______________________________ Exam 4 15. (3 points) What would be the major elimination product obtained from the reaction of each of the following alkyl halides with hydroxide ion? Justify your answer. 16. (3 points) Give each of the following a systematic name, and indicate whether it is a primary, secondary, or tertiary alcohol. 17. (3 points) Give the major products of each of the following reactions. HBr
heat
HCl
Page 6 of 10 Chemistry 231 Summer 2015 July 27, 2015 Name_______________________________ Exam 4 18. (3 points) Give the major product formed when each of the following alcohols is heated in the presence of H2SO4. Justify your answer. 19. (3 points) What alcohol would be required to synthesize each of the following compounds? Justify your answer. 20. (3 points) Give the major product of each of the following reactions. CH3OCH3OH
H+
CH3OH
Page 7 of 10 Chemistry 231 Summer 2015 July 27, 2015 Name_______________________________ Exam 4 21. (6 points) Give the products of the following reactions. HNO3
H2SO4
Cl2
FeCl3
heat
22. (6 points) Give the products of the following reactions. HF
Br2
FeBr3
heat
23. (3 points) Give the major substitution product of the following reaction. heat
Page 8 of 10 Chemistry 231 Summer 2015 July 27, 2015 Name_______________________________ Exam 4 24. (6 points) Which alkyl halide in each pair would you expect to be more reactive in an SN2 reaction with a given nucleophile? Explain. or
or
25. (6 points) Give the major product obtained when each of the following alkyl halides undergoes and E2 reaction. Page 9 of 10 Chemistry 231 Summer 2015 July 27, 2015 Name_______________________________ Exam 4 26. (6 points) Give the major product(s) of the following reactions. If there is no reaction, then write “No reaction”. H2CrO4
H2CrO4
27. (6 points) Give the major product(s) of the following reactions. If there is no reaction, then write “No reaction”. H2SO4
heat
3
H2SO4
heat
28. (3 points) Which compound is likely to be more carcinogenic? Explain. Page 10 of 10