This question has three parts. Please explain your reasoning. This question real

Question

This question has three parts. Please explain your reasoning. This question really confuses me.

Consider the following experiments. In experiment 1, when the tosylate of optically pure S-5-methyl-3 hexanol (A) was treated with sodium formate (HCO_2Na) in formic acid under the indicated conditions, the isolated formate ester was found to be a 3/2 mixture of the R and S enantiomers. B and C. In answering the following questions assume that any unimolecular substitution reaction occurs with complete racemization. What fraction of the products B and C in experiment 1 was formed by an S_n1mechanism? 1/5 2/5 1/2 3/5 4/5 In experiment 2. The same amounts of tosylate A and HCO_2Na were used as in experiment 1 except this time the amount of the formic acid solvent was reduced by a factor of 4. In this experiment what would be the B/C product ratio? 5/2 5/7 4/3 3/1 1/1 In experiment 3, the same amounts of tosylate A and formic acid were used as in experiment 1 except this time only 1/3 as much HCO_2Na was added as in experiment 1 (to reduce the concentration of formate, HCO_2, by a factor of three; the total volume of the solution was the same as in experiment 1). In this experiment what fraction of the products was produced by an S_N2 mechanism? 1/15 1/13 1/12 1/9 1/7

Explanation / Answer

For the given experiment

7. Fraction of products B and C formed by SN1 mechanism,

d. 3/5

SN1 is retention of configuration. So more of product C would be formed in this case. Ratio B/C would reduce.

8. When the amount of solvent was reduced, the ratio of B/C would be,

d. 3/1

Solvent is polar protic, would favor an SN1 reaction. When reduced, it would favor SN2 reaction. More of product B would be formed Ratio B/C is increased.

9. In experiment 3, the amount of nucelophile reagent is reduced, the fraction of products formed by SN2 reaction would be,

d. 1/9

With lower amount of nucleophile, the amount of SN2 product formed in directly reduced as rate depends upon the concentration of nucelophile.

Related Questions

Navigate

• Browse (All)
• Browse T
• Subjects

---

---

Integrity-first tutoring: explanations and feedback only — we do not complete graded work. Learn more.