Substrate
Relative Reaction Rate with AgNO3
Relative Reaction Rate with NaI
1-chlorobutane
4
3
2-chlorobutane
3
2
2-chloro-2-methylpropane
1
4
benzyl chloride
2
1
1-bromobutane
4
3
2-bromobutane
3
4
2-bromo-2-methylpropane
1
2
benzyl bromide
2
1
1-iodobutane
2
2-iodobutane
1
2) For the AgNO3 reaction, do you see any pattern between relative reaction rate and substrate structure?
3) For the NaI reaction, do you see any pattern between relative reaction rate and substrate
structure?
4) Using your data, make a table that will allow you to identify the best leaving group for a particular structure (1°, 2°, 3°, benzylic). What was the best leaving group and what was the worst leaving group? Explain your reasoning by referring to your data.
5) Consider the reaction of 2-chlorobutane with AgNO3 versus NaI. Are the reaction rates the same or different? If the reaction rates are d different, do you think they proceed via the same mechanism? Why or why not (use your data to justify this answer)? Do your experimental findings agree with the theory that you have learned in class?
| Substrate | Relative Reaction Rate with AgNO3 | Relative Reaction Rate with NaI |
| 1-chlorobutane | 4 | 3 |
| 2-chlorobutane | 3 | 2 |
| 2-chloro-2-methylpropane | 1 | 4 |
| benzyl chloride | 2 | 1 |
| 1-bromobutane | 4 | 3 |
| 2-bromobutane | 3 | 4 |
| 2-bromo-2-methylpropane | 1 | 2 |
| benzyl bromide | 2 | 1 |
| 1-iodobutane | 2 | |
| 2-iodobutane | 1 |
2) For the AgNO3 reaction, do you see any pattern between relative reaction rate and substrate structure?
3) For the NaI reaction, do you see any pattern between relative reaction rate and substrate
structure?
4) Using your data, make a table that will allow you to identify the best leaving group for a particular structure (1°, 2°, 3°, benzylic). What was the best leaving group and what was the worst leaving group? Explain your reasoning by referring to your data.
5) Consider the reaction of 2-chlorobutane with AgNO3 versus NaI. Are the reaction rates the same or different? If the reaction rates are d different, do you think they proceed via the same mechanism? Why or why not (use your data to justify this answer)? Do your experimental findings agree with the theory that you have learned in class?
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