Questions tagged [carbene]

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2
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1answer
37 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
votes
1answer
93 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 ...
0
votes
0answers
25 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
votes
1answer
574 views

How does chloroform react with cyclopentadiene in base?

Is my reaction mechanism feasible?
-4
votes
1answer
205 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
votes
2answers
578 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
votes
2answers
499 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
votes
2answers
868 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
votes
1answer
333 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 ...
9
votes
1answer
613 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 ...