Help with Electron Pushing

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Organic Chemistry › Help with Electron Pushing

Questions 1 - 3
1

How many stable resonance structures are there for the following molecule (include the given structure in your total count)?

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5

1

3

4

6

Explanation

The five resonance structures of the given molecule are shown below:

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2

Rank the following compounds in order of increasing rate of electrophilic aromatic substitution.

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V, I, III, IV, II

II, IV, III, I, V

II, I, III, IV, V

V, II, I, III, IV

IV, V, I, III, II

Explanation

The nitro substituent is strongly deactivating, ketones are moderately deactivating substituent, halides are weakly deactivating, alkyl groups are weakly activating, and amine groups are strongly activating.

3

2-butene reacts with (dibromine in a tetrachloromethane solvent). What is the final product?

No reaction

Explanation

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Here we have a classic electrophilic addition reaction.

We must remember that a double bond is an area in a molecule that has a high electron density. As a result, double bonds can act as nucleophiles and react with good electrophiles.

In this problem, the alkene attacks the dibromide to form a bromonium ion, which is rather unstable. The bromonium ion pulls carbon's electrons toward itself, causing the carbons in the bromonium complex to have a slightly negative charge. As a result, the negatively charged bromine can attack either of the carbon atoms and, thus, we have added two bromines to our carbon chain.

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