All Questions
67
questions
2
votes
2
answers
123
views
How to identify an organic base?
According to the answer key, trimethylamine (iii) and ethanolamine (iv) are considered organic bases, whereas ammonium (i) and acrylamide (ii) are not:
From my understanding, an organic base has an ...
- 133
2
votes
0
answers
526
views
Why is the lysine side chain more basic?
As per PubChem: $pK_1 = 2.18$; $pK_2 = 8.95$; $pK_3 = 10.53$ at 38 °C, indicating that the side chain amino group is deprotonated at a higher pH, indicating it is more basic. I tried to justify this ...
- 79
0
votes
1
answer
110
views
Basicity of pyridine and 2,6-di-tert-butylpyridine
Among pyridine and 2,6-di-tert-butylpyridine, which one would be more basic?
My guess was that since two bulky groups are substituted at ortho position in the latter, it will experience steric ...
1
vote
0
answers
82
views
Why is quinuclidine more basic than triethylamine? [duplicate]
I am trying to compare the basic strength of two similar amines
Usually this is done by comparing the relative stability of the ion formed on the protonation of nitrogen's lone pair.
This can be done ...
- 201
0
votes
0
answers
37
views
comparing basic strength of toluidine isomers [duplicate]
I would like to compare the basicity of ortho and para isomers of toluidine.After comparing the pKb values online the order of basic strength is:
p—toluidine> m—toluidine> aniline> o—...
- 156
3
votes
1
answer
634
views
What is the pKa value of the nitrogen atoms, specifically the amine groups?
How would you estimate the $\mathrm pK_\mathrm a$ values of the nitrogen atoms in 1,4-dimethyl-1,2,3,4-tetrahydroquinoxaline?
I struggle with it because I am unsure whether to classify them as ...
- 39
0
votes
1
answer
433
views
What is the order of basicity of amines?
My textbook claims that -
Greater is the stability of the substituted ammonium cation, stronger should be the corresponding amine as a base. Thus, the order of basicity of aliphatic amines should be: ...
- 167
1
vote
1
answer
352
views
Order of basicity for arylamines and ammonia in gas phase
In aqueous solution, the basicity order is: $\ce{NH3 > Ph-NH2 > Ph-NH-Ph > (Ph)3N}$
What will be the order in gas phase?
Following are some considerations:
1- In $\ce{NH3}$, $\ce{N}$ is $\ce{...
- 1,280
3
votes
0
answers
168
views
Is sulphonamide group prone to undergo diazotization?
I wonder if it is not a problem that there is another $\ce{-NH2}$ group in the molecule not connected to aromatic ring and if it can get protonated and react with $\ce{HNO2}$ too, in this case the one ...
- 31
0
votes
1
answer
159
views
Behavior of amines as acids
I came across this question which asked us to find in which alternative does the amine behave as an acid the most:
In which of the following reactions does the amine behave as an acid
(a) $\ce{(C2H5)...
- 513
6
votes
1
answer
650
views
Comparing the basicity of heterocyclic amines
Compare the relative basicity of the following amines.
I know that the higher the electron density on the nitrogen the higher will be its basicity. So here’s my take on each option.
(a)The Nitrogen ...
- 245
8
votes
1
answer
839
views
Comparing acidic strengths between benzylammonium ion and phenol
Question
Compare the acidic stengths between benzylammonium ion and phenol.
I first tried to remove the H+ ion from both of them and tried to compare the relative stabilities of resulting conjugate ...
- 1,261
7
votes
1
answer
3k
views
Why is para-aminobenzoic acid more acidic than ortho-aminobenzoic acid?
Compare the acidic strength of o-, m-, p-aminobenzoic acids.
I got that meta will be the most acidic as it won't be able to show R+ effect of $\ce{NH2}.$
But among the other two, i.e. ortho and para, ...
- 97
3
votes
0
answers
513
views
Why is N,N,2,6-tetramethylaniline less basic than N,N,2-trimethylaniline?
According to me, N,N,2,6-tetramethylaniline should be more basic than N,N,2-trimethylaniline due to more steric inhibition to resonance, but the answer is given opposite. What is the reason for that?
- 147
1
vote
0
answers
27
views
Can the inner amine groups of Bacteriopheophorbide A become positively charged in aqueous solutions without the use of very strong acids?
In an attempt to calculate the pKa of the carboxylic acid group of Bacteriopheophorbide A (BPheo, Pubchem), I generated the structure in MarvinSketch (ChemAxon product) and I came across an ...
- 814