Question

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?

Answer 1

Hi i have included both Microsoft Word Document typed answer as well as printable image with colors; Since this answer window won't accept colored characters.

Q1: AgNO3 proceeds through SN2 mechanism (Inversion of configuration, known as walden inversion)

reaction rate and substrate structure for 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 structure For 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 leaving groups whereas I^- shown rate = 2 & 1

        For NaI all Cl- & Br- have same rate since 3^o substrates shown rate = 4; 2^o substrates shown rate = 3:      

        1^o substrates shown rate = 2; benzyl substrates shown rate = 1

Q4: a) Are the reaction rates the same or different?

Answer: NO, For AgNO₃ rate = 3 ; For NaI rate = 2

        b) If the reaction rates are different, do you think they proceed via the same mechanism?

Answer: AgNO₃ proceeds via SN2 while NaI proceeds via SN1 mechanism

         c) Why or why not (use your data to justify this answer)?

Answer: Consider the reaction of 2-chlorobutane with AgNO₃ versus NaI. For AgNO₃ rate = 3 ; For NaI rate = 2.

        d) Do your experimental findings agree with the theory that you have learned in class?

Answer: YES

Thank You So Much!

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