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14
votes
Accepted
Why is cyclopropane more acidic than propane
answer to see how the hybridization in cyclopropane was determined). … Now, when we compare the hybridization of the $\ce{C-H}$ bonds in cyclopropane and propane we see that there is more s character in the cyclopropane $\ce{C-H}$ bonds, this explains the increased acidity …
27
votes
Why does cyclopropane react with bromine?
The $\ce{H-C-H}$ angle in cyclopropane has been measured to be $114^\circ$. … By the way, an x-ray study of a cyclopropane derivative1 shows significant electron density only exterior to the cyclopropane ring. …
9
votes
Accepted
Why is the addition of a singlet carbene to an alkene stereospecific?
Either 1) a second bond is formed at the same time using the two remaining spin-paired electrons (one on ethylene and one on the carbene) to form cyclopropane in a spin-conserving, concerted addition or … Before the biradical can form the final bond and close to cyclopropane, we must wait for one of the electron spins to flip so that we have a singlet biradical. …
9
votes
Accepted
What's the reaction type of the Hydrogen shift?
counting atoms, 2+0 if we are counting electrons) cycloaddition (adding the carbene's empty $\mathrm{p}$-orbital across the $\ce{C-H}$ bond - analogous to its addition to an olefinic pi bond to produce a cyclopropane …
6
votes
Accepted
Is hybridization of the cyclopropyl anion sp5?
non-equivalent - the resultant hybridization of water
The Question
The $\ce{H-C-H}$ angle in cyclopropane has been measured to be 114°. … Now, if we remove a proton from cyclopropane and generate the cyclopropyl anion, we move from a situation where we had a pair of electrons shared between carbon and hydrogen in a $\ce{C-H}$ bond to a situation …
20
votes
Accepted
Stability Comparison between the Tropylium and Tricyclopropylcarbinyl Carbocation
In fact, the p-character is high enough that a cyclopropane compound will absorb bromine much like an olefin. … In the tricyclopropylcarbinyl carbocation there are 3 cyclopropyl groups stabilizing the carbocation center. …
21
votes
Accepted
Ring contraction in a carbocation due to ring strain and back bonding
In fact, the p-character is so high that a cyclopropane compound will absorb bromine much like an olefin. … In the perpendicular conformation, the cyclopropane $\ce{C-H}$ bond is in the same plane as the carbocation p-orbital, the $\ce{C-C}$ bond is not - there is no carbocation stabilization by the cyclopropane …
20
votes
Accepted
Heats of combustion and stability of rings
Look at the last column ("Total Strain") in Table I, it shows that cyclopropane is slightly more strained than cyclobutane, while cyclopentane and cyclohexane are both much less strained. … Therefore, since cyclopropane has the most ring strain and since propyl, ethyl and methyl groups don't contain any SE, the correct answer to the question is "A". …
16
votes
What is the isomer distribution in monosubstituted fluorobullvalene?
J_\ce{C-H}$ coupling constant in cyclopropane is 161 Hz. Using equations (2) and (1), we find that the C–H bond in cyclopropane has 32% s-character and is $\mathrm{sp^{2.1}}$ hybridized. … So right off the bat, we would expect more fluorine at position 4, than at either of the olefinic positions or the cyclopropyl position.
The relevant $^1\! …
23
votes
3
answers
918
views
What is the isomer distribution in monosubstituted fluorobullvalene?
Considering fluorobullvalene, there are 4 possible isomers:
1-fluorotricyclo[3.3.2.02,8]deca-3,6,9-triene, i.e. the fluorine could be attached to any of the 3 equivalent cyclopropyl carbons
3-fluorotricyclo … could be attached to any of the 3 equivalent olefinic carbons beta to the cyclopropane ring
5-fluorotricyclo[3.3.2.02,8]deca-3,6,9-triene, i.e. the fluorine could be attached to the unique tris-allylic …
5
votes
Accepted
Reactivity of Alkanes
A good example of such behavior can be found in cyclopropane. … Indeed, cyclopropane adds bromine much like an alkene (ref. 3)
Since someone above commented that ${sp^3}$ $\ce{C-H}$ bonds are "very stable and typically do not want to react". …
10
votes
Accepted
Orbital correlation diagram for the cleavage of cyclopropylmethylene carbene
The rear cyclopropane bond is bisected by the plane of the screen, this plane also contains the cyclopropyl carbon connected to the carbene center. … Like when we break a bond in cyclopropane we have a 1,3-biradical. …
18
votes
Accepted
Formation of a stable hydrate
You've already figured out why cyclopropanone exists as a hydrate. So the correct answer is B, since there is no driving force that would provide any special stabilization of its hydrate. …
9
votes
Nucleophilic attack at a carbonyl - angle of attack
the reaction as an $\mathrm{SN2}$ reaction
Use trigonometry to deduce the angle of nucleophilic approach
The bent-bond model is widely used in chemistry to describe highly-strained systems such as cyclopropane …
15
votes
Why can there not be more than one sigma bond in a set of bonds?
In order to better understand the bent bond model let's first consider its application to cyclopropane and then move to ethylene. … (image source)
Further, the $\ce{H-C-H}$ angle in cyclopropane has been measured and found to be 114 degrees. …