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Chapter 9: Problem 1

Complete the following nucleophilic substitution reactions. In each reaction, show all electron pairs on both the nucleophile and the leaving group.

Short Answer

Expert verified
Answer: In a nucleophilic substitution reaction, the nucleophile is usually a negatively charged species or a molecule with lone pair electrons, while the leaving group is typically a halide ion or a similar electron-withdrawing group attached to the carbon atom. Showing the movement of electron pairs using curved arrow notation illustrates the mechanism of the reaction, highlighting the attack of the nucleophile on the electrophilic carbon and the departure of the leaving group. This helps in understanding the process and predicting the products of the reaction.

Step by step solution

01

Identify the nucleophile and leaving group

Identify the nucleophile (Nu) and the leaving group (X) in the reaction. In a general SN2 reaction, the nucleophile can be any negatively charged species or a molecule with lone pair electrons, and the leaving group is usually a halide ion or a similar electron-withdrawing group attached to the carbon atom. For example, consider a reaction between alkyl bromide (CH3-Br) and hydroxide ion (OH-). Here, OH- is the nucleophile, and Br- is the leaving group.
02

Show the movement of electron pairs

In an SN2 reaction, the nucleophile attacks the carbon atom to which the leaving group is attached, from the opposite side of the leaving group. Show the movement of electron pairs by using curved arrow notation: 1. Draw a curved arrow from the lone pair of electrons on the nucleophile (Nu) to the electrophilic carbon atom (C) attached to the leaving group (X). 2. Draw another curved arrow from the bond between the carbon atom (C) and the leaving group (X) to the leaving group (X), indicating the breaking of the bond and the leaving group acquiring a negative charge. For the example reaction (CH3-Br + OH-), the curved arrow notation would look like this: OH:¯ ---> CH3-Br ---> Br:¯
03

Draw the products of the reaction

After showing the movement of electron pairs, draw the products of the nucleophilic substitution reaction. In an SN2 reaction, the nucleophile forms a bond with the electrophilic carbon, and the leaving group departs with a negative charge. For the example reaction (CH3-Br + OH-), the final product would be: CH3-OH + Br:¯ Now you should be able to show the steps of a nucleophilic substitution reaction, including all electron pairs on both the nucleophile and the leaving group. Always remember to identify the nucleophile and leaving group, show the movement of electron pairs using curved arrow notation, and then draw the products of the reaction.

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Most popular questions from this chapter

Show how you might synthesize the following compounds from a haloalkane and a nucleophile:

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.

Draw a structural formula for the most stable carbocation with each molecular formula. (a) \(\mathrm{C}_{4} \mathrm{H}_{9}{ }^{+}\) (b) \(\mathrm{C}_{3} \mathrm{H}_{7}^{+}\) (c) \(\mathrm{C}_{5} \mathrm{H}_{11}^{+}\) (d) \(\mathrm{C}_{3} \mathrm{H}_{7} \mathrm{O}^{+}\)

When cis-4-chlorocyclohexanol is treated with sodium hydroxide in ethanol, it gives mainly the substitution product trans-1,4-cyclohexanediol (1). Under the same reaction conditions, trans-4-chlorocyclohexanol gives 3-cyclohexenol (2) and the bicyclic ether (3).

Attempts to prepare optically active iodides by nucleophilic displacement on optically active bromides using I \(\mathrm{I}^{-}\)normally produce racemic iodoalkanes. Why are the product iodoalkanes racemic?
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