3. Consider the following Sw2 reaction: .. solvent solvent NC dimethyl formamide

Question

3. Consider the following Sw2 reaction: .. solvent solvent NC dimethyl formamide 1,200,000 H methyl formamide formamide Relative rate (M/s)12.5 Section 6-8 Vollhardt & Schore 45.3 a. (1 point) What is the variable in this study? b. (1 point) What is (are) the data trend(s)? c. (1 points) What do the data trends tell us about the Sw2 mechanism? The transition state is needed to explain Sw2 reactivity. Draw two formamide molecules to show where they are likely to intervene to slow down an Sw2 reaction Why does the reaction in formamide and methyl formamide solvent slow down the reaction?

Explanation / Answer

a) Solvent is the variable in this study.

b) The data trend shows that with increasing number of methyl (alkyl) group, the reaction rate increases. This is because replacement of -H with -CH3 group prevents the hydrogen bond formation to the nucleophile, thus increasing the reactivity rate.

c) The data trend tells us that SN2 reaction is highly dependent on the type of solvent used. The use of polar protic solvent hinders the reaction.

The reaction in formamide and methyl formamide slows down due to formation of hydrogen bond between solvent molecule and the nucleophile. This hinders the reaction in both the case.

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