Linked Questions

0 votes
0 answers
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Factor affecting acidity:Hybridization [duplicate]

I have problem here So I had learn that the percent of s-character of hybrid orbital will affect the bond strength. The higher percentage of s-character,the stronger the bond.For example the strength ...
Sheng Lee's user avatar
0 votes
0 answers
39 views

If Ethyne has the lowest C-H bond length (highest C-H bond energy) compared to Ethane and Ethene, why is it the most acidic? [duplicate]

I am not an expert in chemistry, but these are the few facts I know from Standard XII chemistry books (these facts could be wrong or incomplete or modified by now). Facts I know - Ethane has 'sp$^3$' ...
Souparna Nath's user avatar
-1 votes
1 answer
865 views

Why do terminal alkynes have lower pKa values than non-terminal alkynes?

We were asked in class which have the lower $\mathrm{p}K_\mathrm{a}$ values: terminal alkynes or non-terminal alkynes. The teacher told that terminal alkynes have the lowest $\mathrm{p}K_\mathrm{a}$ ...
Aniruddha's user avatar
  • 462
2 votes
1 answer
602 views

The most acidic hydrogen among ethane, ethene, ethyne and allene

Among $$\ce{CH3-CH3}\qquad\ce{CH2=CH2}\qquad\ce{HC≡CH}\qquad\ce{CH2=C=CH2}$$ I need to find out the one having highest acidic hydrogen. As per my observations, there are two equivalent resonating ...
Sanu_012's user avatar
  • 307
3 votes
1 answer
451 views

C−H bond length in organic compounds [duplicate]

I am reading Fundamental concepts of organic chemistry by Dr. Anju Srivastava (12/04/2007). It shows that carbon-hydrogen bond in ethane is 1.1 Å long, in ethene it's 1.08 Å, and in ethyne it's 1.06 ...
Hon Bisaso Ismail's user avatar
3 votes
1 answer
3k views

Which would be more acidic, benzene or cyclohexane?

If benzene were to donate a hydrogen ion, then could the negative charge still be delocalised around the ring? Wouldn't that break aromaticity and thus destabilise the molecule?
kytosine's user avatar
  • 377
17 votes
2 answers
20k views

Predicting sigma bond overlap strengths of s-s, p-p, s-p, sp-sp etc

How can we qualitatively predict $\sigma-$bond strengths of overlap between: $\ce{s-s}$ $\ce{s-p}$ $\ce{p-p}$ $\ce{sp-s}$ $\ce{sp-p}$ $\ce{sp-sp}$ etc.? My school-book says $\ce{s-s}$ overlap bond ...
jonsno's user avatar
  • 701
0 votes
0 answers
137 views

Why is an alkenyl hydrogen more acidic than the alkyl analog?

For example, in ethene the sigma bonds are stronger overall than in ethane. ...
ttdijkstra's user avatar
8 votes
1 answer
2k views

Why is ammonia more basic than acetonitrile

Why is $\ce{NH_3}$ more basic than $\ce{CH3CN}$? I tried to reason it out with the hybridization of nitrogen in both the molecules. In $\ce{NH_3}$ nitrogen is $\mathrm{sp^3}$ hybridized while in ...
oshhh's user avatar
  • 836
2 votes
0 answers
2k views

Why is an alkyne more acidic than an alkene? Or, why is acetylene more acidic than ethylene?

pKa acetylene ~ 25 pKA ethylene ~ 44 I'm not looking for the "because alkyenes are sp hybridized and more s character means their electrons are held tighter" answer because I'm not the biggest fan ...
Nova's user avatar
  • 1,782
7 votes
1 answer
6k views

Which dicarboxylic acid has the most acidic hydrogen?

Which of the following acids (maleic, fumaric, succinic, or malonic) has the most acidic hydrogen? I think that malonic acid should have the most acidic hydrogen due to the presence of an active ...
Prakhar's user avatar
  • 2,391
5 votes
5 answers
10k views

Which proton in cyclohexene is the most acidic?

I know that $\mathrm{H^b}$ is most acidic due to conjugation (resonance). But I am confused as to how to compare $\mathrm{H^a}$ and $\mathrm{H^c}$. I think $\mathrm{H^a}$ should be more acidic than $\...
user101522's user avatar
13 votes
2 answers
22k views

Reactions of alkynes with sodium/ammonia vs sodium amide

What happens when alkynes react with sodium in ammonia ($\ce{Na/NH3}$), or when they react with sodium amide ($\ce{NaNH2}$)? Are these two sets of conditions different?
geek101's user avatar
  • 1,051
15 votes
1 answer
14k views

Why does acetylene, having an acidic proton, not react with strong bases like NaOH and KOH?

In acetylene (ethyne, HC≡CH), the carbons are sp-hybridised, which make the attached protons more acidic than those in alkenes or alkanes. (See also: Relative acidities of alkanes, alkenes, and ...
Ris97's user avatar
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