Question

hi, i need to solve this synthesis to form this desired product from benzene. I could use any reactants. all I know is that nitration can be used to transform into an aniline. Thank you!

8ac3282230d7342a20346b09eeec957f.pdf

Answer 1

Answer:

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Answer 2

Explanation:

nucleophilic aromatic substitution, but with a new twist; a nucleophilic aromatic substitution that passes through a strange-looking intermediate called an aryne (a generic term for a family of molecules that includes benzyne).

Table of Contents

Nucleophilic Aromatic Substitution – A Quick Recap

A “Nucleophilic Aromatic Substitution” In Name, But By A Different Mechanism

The “Benzyne” Intermediate

Reaction of Substituted Benzyne – “Arynes”

Benzyne Undergoes Diels-Alder Reactions

The Structure of Benzyne

Summary: Nucleophilic Aromatic Substitution via Benzyne

Notes

Quiz Yourself!

(Advanced) References and Further Reading

1. Quick Recap: Nucleophilic Aromatic Substitution

Previously [see: Nucleophilic Aromatic Substitution] we saw that electron-poor aromatic rings containing a leaving group can undergo substitution with electron-rich nucleophiles. We saw that the mechanism proceeds through addition of a nucleophile to the aromatic ring (via an electron-rich intermediate) followed by loss of a leaving group, in a process sometimes called, “addition-elimination”.

nucleophilic aromatic substitution mechanism summary addition elimination

Importantly, the only substitution product is the one where the nucleophile ends up attached to the same carbon as that bearing the leaving group. (This differentiates it from electrophilic aromatic substitution, where a mixture of ortho-, para– and meta- products can be obtained.)

2. A “Nucleophilic Aromatic Substitution” In Name, But By A Different Mechanism

Although the “addition-elimination” mechanism for nucleophilic aromatic substitution has been known since at least 1902 (when Meisenheimer isolated a key intermediate) , it became increasingly clear in the first half of the twentieth century that certain reactions classified as “nucleophilic aromatic substitution” appeared to proceed through a different mechanism altogether.

For example, it was found that treating chlorobenzene with sodium amide (NaNH2) in liquid ammonia (boiling point = –33°C) resulted in the rapid formation of aminobenzene (“aniline”):