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Chapter 9: Problem 19

What hybridization best describes the reacting carbon in the \(S_{N} 2\) transition state?

Short Answer

Expert verified
Answer: The hybridization of the reacting carbon atom in the \(S_{N} 2\) transition state is sp\(^3\).

Step by step solution

01

Understanding the \(S_{N} 2\) reaction mechanism

The \(S_{N} 2\) reaction, or bimolecular nucleophilic substitution, is a reaction in which a nucleophile attacks an electrophilic carbon attached to a leaving group. The reaction proceeds through a single concerted step with the nucleophile attacking the carbon center while the leaving group simultaneously departs. The important aspect of this transition state is that the nucleophile and leaving group are partially bonded to the reacting carbon.
02

Identify the number of electron domains around the reacting carbon

In an \(S_{N} 2\) transition state, the reacting carbon has four electron domains: three from the initial compound and one from the attacking nucleophile. The three initial electron domains are 1) other atoms bonded to the reacting carbon, 2) the bond that is being broken with the leaving group, and 3) the bond that is being formed with the nucleophile.
03

Determine the hybridization based on the electron domains

Since we have four electron domains, and all of them are single bonds (the partial bond with the nucleophile is considered as a single bond as well), this suggests that the hybridization of the reacting carbon atom in the \(S_{N} 2\) transition state is sp\(^3\). In an sp\(^3\) hybridized orbital, there is one s-orbital and three p-orbitals, which allows the carbon atom to form four single bonds.

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Most popular questions from this chapter

Elimination of HBr from 2-bromonorbornane gives only 2-norbornene and no 1-norbornene. How do you account for the regioselectivity of this dehydrohalogenation? In answering this question, you will find it helpful to look at molecular models of both 1-norbornene and 2-norbornene and to analyze the strain in each.

From each pair, select the stronger nucleophile. (a) \(\mathrm{H}_{2} \mathrm{O}\) or \(\mathrm{OH}^{-}\) (b) \(\mathrm{CH}_{3} \mathrm{COO}^{-}\)or \(\mathrm{OH}^{-}\) (c) \(\mathrm{CH}_{3} \mathrm{SH}\) or \(\mathrm{CH}_{3} \mathrm{~S}^{-}\) (d) \(\mathrm{Cl}^{-}\)or \(\mathrm{I}^{-}\)in DMSO (e) \(\mathrm{Cl}^{-}\)or \(\mathrm{I}^{-}\)in methanol (f) \(\mathrm{CH}_{3} \mathrm{OCH}_{3}\) or \(\mathrm{CH}_{3} \mathrm{SCH}_{3}\)

Draw a structural formula for the product of each \(\mathrm{S}_{\mathrm{N}} 2\) reaction. Where configuration of the starting material is given, show the configuration of the product.

Using your roadmap as a guide, show how to convert 2-methylbutane into racemic 3-bromo-2-methyl-2-butanol. Show all reagents and all molecules synthesized along the way.

The following nucleophilic substitution occurs with rearrangement. Suggest a mechanism for formation of the observed product. If the starting material has the \(S\) configuration, what is the configuration of the stereocenter in the product?
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