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Please write answers in the page to show which answer goes with the question 5 M

ID: 580884 • Letter: P

Question

Please write answers in the page to show which answer goes with the question

5 MODULE 1 Analyzing Processes Your UANet ID The molecular structure of the electrophile has a big impact on the rate of substitution reactions, on the mechanism of the reaction, and on the nature of the product. The rate of substitution is also affected by the nature of the nucleophile. LET'S THINK Kinetic Analysis: The Nucleophile The strength of a nucleophile is a measure of how fast it reacts to produce the substitution product. For substitution reactions that proceed via an S 2 mechanism, the table below shows the ratio of the rate of substitution of different nucleophiles to the reaction rate when the nucleophile is water: OH- 5 x 102 3.2 x 1031.6 x 1045.0x 104 1.2 x 105 F- Cl Br CN 1 1 x 102 Propose a reasonable explanation for the trend in increasing rate of substitution for the nucleophiles represented above. (HINT: Consider energetic and entropic factors that may facilitate the attachment of the nucleophile and its stability in the surrounding solvent) The rate of substitution reactions that proceed via an S1 mechanism is not affected by either the concentration or the strength of the nucleophile. How would you explain this? LET'S THINK Apply what you know CH Imagine that you wanted to synthesize the compound shown to the right. You have access to sodium cyanide (NaCN) as nucleophile. What compound would you use as a reactant in combination with NaCN to produce the product shown to the right using a substitution reaction? Justify your choice. Write the overall chemical equation for the reaction.

Explanation / Answer

Q1

Trend:

The "bulkier" the group, the faster rate

this can be seen for F- <Cl- <br- < I- tendency

as well as CN- being very bulky as well

b)

rate of combustion implies lots of breaking of bonds, therefore, the collision between fuel /oxidant will not require that "SN2 / E2" rate