Linked Questions

0 votes
0 answers
30 views

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 ...
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$^3$' ...
-1 votes
1 answer
866 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 $\mathrm{p}K_\mathrm{a}$ ...
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?
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 ...
3 votes
1 answer
452 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 ...
2 votes
1 answer
604 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 ...
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 ...
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 $\...
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 ...
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?
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. ...
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 ...
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 ...