1 Answer. Show activity on this post. Only a very small fraction of the benzyl alcohol (pKa=15.4) would be removed by sodium hydroxide. Acetic acid is about 10 orders of magnitude more acidic than benzyl alcohol with a pKa of 4.8, so it is completely deprotinated to form sodium acetate and water.
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Can NaOH deprotonate benzyl alcohol?
1 Answer. Show activity on this post. Only a very small fraction of the benzyl alcohol (pKa=15.4) would be removed by sodium hydroxide. Acetic acid is about 10 orders of magnitude more acidic than benzyl alcohol with a pKa of 4.8, so it is completely deprotinated to form sodium acetate and water.
What happens when alcohol reacts with NaOH?
No. Alcohols are very weak acids and do not react with NaOH.
What bases can deprotonate alcohols?
A strong base can deprotonate an alcohol to yield an alkoxide ion (R―O−). For example, sodamide (NaNH2), a very strong base, abstracts the hydrogen atom of an alcohol. Metallic sodium (Na) or potassium (K) is often used to form an alkoxide by reducing the proton to hydrogen gas. Alkoxides can be useful reagents.
Is NaOH strong enough to deprotonate?
NaOH has pKa 15.7 and is not strong enough to deprotonate acid 5. This is called the solvent levelling effect: in any solvent, the strongest base that can exist is the conjugate base of the solvent.
Which is aromatic alcohol?
In organic chemistry, the aromatic alcohols or aryl-alcohols are a class of chemical compounds containing a hydroxyl group (—OH) bonded indirectly to an aromatic hydrocarbon group, in contrast to the phenols, where the hydroxyl group is bonded directly to an aromatic carbon atom.
Are alcohols soluble in NaOH?
In general most alcohols are slightly less acidic than water. In aqueous NaOH, there are mobile Na+ and OH-, so alcohol is not able to react with Na+ to form water and salt , as it can be considered as an acid. Thus the main conclusion that can be drawn is that alcohol can not react with NaOH.
Why are alcohols insoluble in NaOH?
Because of the aq. NaOH when reacts with water forms ethoxide ion but due to its basicity it abstract hydrogen reforming alcohol. hence alcohols does not reacts with the base.
Can NaOH deprotonate carboxylic acid?
To deprotonate phenols, thiols or carboxylic acids, you should use sodium hydroxide (NaOH) or potassium carbonate as the base.
Can NaOH deprotonate a terminal alkyne?
To deprotonate terminal alkynes, sodium hydroxide will not work. Instead, you should use sodium amide (NaNH2).
What can deprotonate water?
The corresponding conjugate bases, H-C≡C:-,H2N:- , and H3C:- , are strong. They will all deprotonate water. The conjugate base of methane H3C:- is strong enough to deprotonate anything below it in the table. Methyllithium, CH3Li , is one of the strongest bases around.
Does deprotonation increase pH?
The pKa of the carboxylic acid is always lower than that of the ammonium group. As pH increases, it will be deprotonated before the ammonium group. For the amino acids with protonated R groups, you need to pay attention to their pKa values. The atom with the lowest pKa will be deprotonated.
Are phenols aromatic alcohols?
Although phenols are often considered simply as aromatic alcohols, they do have somewhat different properties. The most obvious difference is the enhanced acidity of phenols. Phenols are not as acidic as carboxylic acids, but they are much more acidic than aliphatic alcohols, and they are more acidic than water.
Does NaOH deprotonate benzyl alcohol?
I realize that NaOH generally does not deprotonate benzyl alcohol, but we performed an extraction in a Fischer esterification lab with benzyl alcohol an acetic acid to synthesize benzyl acetate. Acetic acid was added in excess, and the final ester product was purified with extraction techniques.
How to deprotonate ethyl alcohol with sodium metal?
You said you have ethyl alcohol , you can use sodium metal to deprotonate your alcohol at about zero degree (ice bath),and also do your reaction at this low temperature. You might try triethylamine.
Does sodium hydroxide remove benzyl alcohol from sodium acetate?
Only a very small fraction of the benzyl alcohol ( p K a = 15.4) would be removed by sodium hydroxide. Acetic acid is about 10 orders of magnitude more acidic than benzyl alcohol with a p K a of 4.8, so it is completely deprotinated to form sodium acetate and water.
How do you deprotonate phenol?
There is quite a lot of options and we can pick any of them. For example, we will pick the alcohol and use ethanol on the product’s side. This means that the B – should be the conjugate base of the ethanol. So ethoxide (with a counter ion) can be used to deprotonate the phenol.