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Questions tagged [carbene]

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Major Organic Product of pheylpropene and diazomethane? [closed]

What is the major organic product synthesized from phenylpropene and diazomethane? I get that N2 from the diazomethane is going to be the leaving group correct and it forms the carbene :CH2 correct? ...
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0answers
37 views

Hydrogen Bonding by Carbenes

A hydrogen bond is formed between hydrogen attached to highly electronegative atoms (nitrogen, oxygen, and fluorine) which are small in size too and the non-bonding pair of electrons of another such ...
2
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1answer
52 views

How is chlorocarbene synthetised?

The wikipedia page on cyclononatetraene says that the aromatic cyclononatetraenyl anion can be synthetised by a rearangement of 9-chlorobicyclo[6.1.0]nona-2,4,6-triene. My first idea on how to ...
4
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1answer
146 views

Mechanism of Fritsch–Buttenberg–Wiechell rearrangement

The following reaction was given, which uses potassium t-butoxide. The solution to this problem was given as follows: Step 1 is the attack of strong base, t-butoxide, on the vinyl proton. Step 2 ...
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0answers
32 views

Cyclic pent-diene + CHBr3 + t-BuOK. What is the product and how is it formed? [duplicate]

I think the answer is Bromo-Benzene but I am not sure. Please also provide the mechanism as to how the product is obtained.
5
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1answer
754 views

How does chloroform react with cyclopentadiene in base?

Is my reaction mechanism feasible?
-4
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1answer
237 views

reimer tieman reaction only one ortho product [closed]

why we cannot have two reimer tiemann substitutions on the same phenol as CHO- group is electron withdrawing it wont disturb electron concentration at its meta which is phenol's ortho- product
10
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2answers
641 views

Reaction between a carbene and n-pentane

Does the following reaction occur when n-pentane reacts with methylene or does it form some other simpler products due to the reactivity of the carbene? $\ce{CH3-(CH2)3-CH3 + :CH2-> CH3-(CH2)4-CH3}...
9
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2answers
545 views

Correct way to draw a carbene

What is the correct way to draw a carbene? On most/all material I have seen, both singlet and triplet carbenes are depicted as so: With 2 "dots" representing the non-bonding electrons on either a ...
8
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2answers
1k views

Why is triplet carbene sp2-hybridised?

Triplet carbene has a carbon with 6 electrons, of which 2 are unpaired. I would expect the carbon to be $\ce{sp}$ or $\ce{sp^3}$ hybridised and the two singly occupied orbitals to be degenerate. ...
3
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1answer
336 views

Origin of diastereoselectivity in Simmons–Smith cyclopropanation of allylic alcohol

In Organic Chemistry by Clayden et al., the following reaction is shown: The cyclopropane ring is formed on the same side as the alcohol group. Is this because of the interaction between Zn and the ...
7
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1answer
674 views

Which singlet dihalocarbene has the strongest carbon-halogen bond?

There are three singlet carbenes - difluorocarbene, dichlorocarbene and dibromocarbene. Which has the strongest carbon halogen bond? Obviously backbonding is a point to be considered, as carbene is ...