Linked Questions

1 vote
2 answers
7k views

Does the amine group participate in resonance in aniline? [duplicate]

When we draw resonance structures of aniline, 8 electrons participate in resonance, making it antiaromatic. But in our school textbook, it is said to be aromatic. Does the lone pair of $\ce{NH2}$ ...
YAHB's user avatar
  • 897
1 vote
1 answer
3k views

Why is styrene an aromatic compound? [duplicate]

Why is styrene aromatic? Doesn't it have 8 pi electrons, thereby violating Hückel's rule? Can someone offer an alternate, more through explanation?
edbert's user avatar
  • 11
0 votes
2 answers
154 views

Aromaticity of chlorobenzene [duplicate]

Hückel's rule predicts that; a planar ring molecule will have aromatic properties if it has 4n+2 π electrons in conjugation. If 4n π electrons are in cyclic conjugation, then it is anti-aromatic. So, ...
BK01's user avatar
  • 55
38 votes
4 answers
21k views

Is pyrene aromatic despite failing Hückel's rule?

Pyrene doesn't seem to be aromatic. However, sources claim that it is aromatic. Considerations: Pyrene is cyclic. ✓ Pyrene is flat (planar). ✓ Pyrene has 16 π electrons. Every atom in the ring ...
Dissenter's user avatar
  • 19k
12 votes
2 answers
30k views

Is nitrogen of aniline sp² or sp³ hybridized? [duplicate]

I found a thread which discussed this which totally confused me. (refer to the part of the link which talks about $\ce{sp^2/sp^3}$) The question "How to rationalise the resonance structures and ...
Wong's user avatar
  • 123
27 votes
1 answer
4k views

What is the justification for Hückel's rule?

I know that experimentally, the rule has been verified but I am having trouble understanding why it works. I see no reason why equivalent cyclic structures can undergo resonance and be just as stable. ...
CognisMantis's user avatar
  • 1,648
8 votes
2 answers
1k views

Can a cyclic amine form an amide?

This is a question from the Cambridge International Examinations October/November 2017 (pdf from papers.gceguide.com, pdf via the Wayback Machine). I need to understand why the secondary amine in the ...
Amar30657's user avatar
  • 301
5 votes
3 answers
4k views

Do the π-electrons from the C=O bond in tropone contribute to Hückel 's rule?

This is a continuation of Is tropone aromatic? I'm looking at the resonance form that does have the carbonyl double-bond, 1a. Can this resonance structure also be considered aromatic? Would the ...
yolo123's user avatar
  • 1,845
-2 votes
2 answers
2k views

Is Magnesium Oxide alkali [closed]

Given that Magnesium Hydroxide is an alkali, can we say Magnesium Oxide is an alkali since dissolving Magnesium Oxide in water can produce Magnesium Hydroxide?
Diamond Science's user avatar
1 vote
1 answer
396 views

Generalizations regarding functional groups on benzene ring

While studying several organic mechanisms (high school level), I came to an interesting generalization. I claim that negative charge on phenoxide ion first ALWAYS delocalises onto the ring and then ...
Gaurang Tandon's user avatar