Skip to main content
Search type Search syntax
Tags [tag]
Exact "words here"
Author user:1234
user:me (yours)
Score score:3 (3+)
score:0 (none)
Answers answers:3 (3+)
answers:0 (none)
isaccepted:yes
hasaccepted:no
inquestion:1234
Views views:250
Code code:"if (foo != bar)"
Sections title:apples
body:"apples oranges"
URL url:"*.example.com"
Saves in:saves
Status closed:yes
duplicate:no
migrated:no
wiki:no
Types is:question
is:answer
Exclude -[tag]
-apples
For more details on advanced search visit our help page
Results for cycloprop*
Search options not deleted user 4231
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 …
Mathew Mahindaratne's user avatar
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. …
Mathew Mahindaratne's user avatar
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. …
Mathew Mahindaratne's user avatar
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
Mathew Mahindaratne's user avatar
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 …
ron's user avatar
  • 85.4k
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. …
Martin - マーチン's user avatar
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
ron's user avatar
  • 85.4k
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". …
user55119's user avatar
  • 17.5k
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\! …
ron's user avatar
  • 85.4k
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". …
Community's user avatar
  • 1
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. …
ron's user avatar
  • 85.4k
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. …
ron's user avatar
  • 85.4k
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
Community's user avatar
  • 1
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. …
ron's user avatar
  • 85.4k

15 30 50 per page