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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. …
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 …
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. …
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 …
6
votes
Accepted
Reactivity of propellanes
Cyclopropane and cyclobutane have roughly the same strain energy (SE=27.5 and 26.3 kcal/mol respectively). … Each of the 3 starting materials contains a total 3 (cyclopropane plus cyclobutane) rings. …
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". …
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\! …
15
votes
Accepted
Is tropone aromatic?
On this basis, molecules like the cyclopropenyl cation (4n+2, n=0), benzene (n=1), cycloheptatriene (tropylium) cation (n=1), cycooctatetraene dianion (n=2) would be considered aromatic systems. … Correspondingly, the cyclopropenyl anion (4n, n=1), cyclobutadiene (n=1), cyclopentadienyl cation (n=1), cyclooctatetraene (if it were a planar molecule, n=2) are considered destabilized or anti-aromatic …
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. …
7
votes
Accepted
Making three membered ring using different reactants
Carbenes are very reactive intermediates, reactive enough to add to a double bond and form a strained 3-membered ring (a cyclopropane).
The reaction you've shown is said to be stereospecific. … That is, you started with cis-2-butene and wound up with a cis-dimethyl-dichlorocyclopropane; the cis olefin geometry is preserved in your cyclopropane product. …
12
votes
Accepted
Ring expansion from a given cyclic carbocation
Note: this question has been asked previously on SE Chem, however I believe the accepted answer is incorrect, as it seems to primarily address the cyclopropyl carbinyl case, and what is said about the …
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. …
4
votes
Accepted
Are the p orbitals of the biradical dioxo compound in the HOMO perpendicular to the plane?
Let's start by using cyclopropane as a model compound. … In cyclopropane the $\ce{C-H}$ bonds are approximately $\ce{sp^{2.46}}$ hybridized and the $\ce{C-C}$ bond is approximately $\ce{sp^{3.74}}$ hybridized (see here). …
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 …