Substrate Relative Reaction Ra
|
Substrate |
Relative Reaction Rate withAgNO3 |
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 AgNO3reaction, do you see any pattern between relative reaction rate andsubstrate structure?
3) For the NaI reaction, do you seeany pattern between relative reaction rate andsubstrate
structure?
4) Using your data, make a table that will allow you to identifythe best leaving group for a particular structure (1°, 2°, 3°,benzylic). What was the best leaving group and what was the worstleaving group? Explain your reasoning by referring to yourdata.
5) Consider the reaction of2-chlorobutane with AgNO3 versus NaI. Are the reactionrates 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 experimentalfindings agree with the theory that you have learned in class?
Answer:
Hi i have included both Microsoft Word Document typedanswer as well as printable image with colors; Since this answerwindow won’t accept colored characters.
Q1: AgNO3 proceeds through SN2 mechanism(Inversion of configuration, known as walden inversion)
|
reaction rate and substrate structurefor AgNO3 |
Mechanism follows |
best leaving group |
worst leaving group |
|
1o > 2o >Benzyl > 3o |
SN2 |
Cl- and Br- |
I- |
Q2: NaI proceeds through SN1mechanism(racemization, mixture of both isomers)
|
reaction rate and substrate structureFor NaI |
Mechanism follows |
best leaving group |
worst leaving group |
|
3o > 1o >2o > Benzyl |
SN1 |
Cannot say about this |
|
Q3: For AgNO3 both Cl–& Br– shown rate =4 & 3 means best leavinggroups whereas I– shown rate = 2 & 1
For NaI all Cl- &Br- have same rate since 3o substrates shown rate = 4;2o substrates shown rate = 3:
1osubstrates shown rate = 2; benzyl substrates shown rate = 1
Q4: a) Are the reaction ratesthe same or different?
Answer: NO, For AgNO3 rate = 3 ; ForNaI rate = 2
b)If the reaction rates are different, do you think they proceed viathe same mechanism?
Answer: AgNO3 proceeds via SN2 whileNaI proceeds via SN1 mechanism
c) Why or why not (use your data to justify thisanswer)?
Answer: Consider the reaction of 2-chlorobutanewith AgNO3 versus NaI. For AgNO3 rate = 3 ;For NaI rate = 2.
d)Do your experimental findings agree with the theory that you havelearned in class?
Answer: YES
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