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Chapter 1: Problem 163

The most reactive among the nucleophiles given is (a) \(-\mathrm{OCH}_{3}\) (b) \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{O}^{-}\) (c) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{O}^{-}\) (d) \(\left(\mathrm{CH}_{3}\right)_{3} \mathrm{CO}^{-}\)

Short Answer

Expert verified
(a) -OCH₃, (b) C₆H₅O⁻, (c) CH₃CH₂O⁻, and (d) (CH₃)₃CO⁻. Answer: The most reactive nucleophile among the given options is (a) -OCH₃ (methoxide).

Step by step solution

01

Identifying the Negative Charge of the Nucleophiles

In this step, let's identify the negative charge of each nucleophile. (a) \(-\mathrm{OCH}_{3}\): The negative charge is on the oxygen atom. (b) \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{O}^{-}\): The negative charge is on the oxygen atom. (c) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{O}^{-}\): The negative charge is on the oxygen atom. (d) \(\left(\mathrm{CH}_{3}\right)_{3} \mathrm{CO}^{-}\): The negative charge is on the oxygen atom. Since all have a negative charge on the oxygen atom, let's move on to the next factor.
02

Analyzing the Size and Electronegativity of the Nucleophiles

In this step, we need to look at the other factors related to the nucleophiles to help determine their reactivity. (a) \(-\mathrm{OCH}_{3}\): The methoxide ion is relatively small and has a high electronegativity. (b) \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{O}^{-}\): The phenoxide ion is stabilized by resonance within the benzene ring, reducing its reactivity. (c) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{O}^{-}\): The ethoxide ion is slightly larger than methoxide, but not as large or resonance-stabilized as phenoxide. (d) \(\left(\mathrm{CH}_{3}\right)_{3} \mathrm{CO}^{-}\): The tert-butoxide ion is much larger in size than the other nucleophiles, which decreases its reactivity.
03

Comparing the Nucleophiles

In this step, we will compare the nucleophiles based on the previous observations. (a) \(-\mathrm{OCH}_{3}\): Small and highly electronegative (reactive) (b) \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{O}^{-}\): Resonance stabilized (less reactive) (c) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{O}^{-}\): Slightly larger than methoxide, but not resonance-stabilized (fairly reactive) (d) \(\left(\mathrm{CH}_{3}\right)_{3} \mathrm{CO}^{-}\): Large and bulky (least reactive)
04

Conclusion

Based on the analysis, the most reactive nucleophile among the given options is (a) \(-\mathrm{OCH}_{3}\), also known as methoxide.

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Most popular questions from this chapter

A meso compound (a) is an achiral molecule, which contain chiral carbons. (b) contains a plane of symmetry or a centre of symmetry. (c) is optically inactive due to internal compensation. (d) is characterized by all the above.

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