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Questions tagged [hydrolysis]

Hydrolysis refers to any reaction with water. For example, it may be said that ammonia hydrolyzes in water to produce ammonium ion and hydroxide ion.

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18
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1answer
1k views

What makes C=O more stable that C(OH)₂

When there are $2$ hydroxy groups on same carbon, they tend to undergo dehydration ( of course with exceptions like chloral where $\ce H$ bonding prevails). Why does this happen? We are breaking a ...
14
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1answer
2k views

Mechanism for basic hydrolysis of α-chloronitrile to ketone?

In Corey's 1969 prostaglandin synthesis,1 compound 2 is formed from compound 1 by: [...] treatment with 2.5 equiv of potassium hydroxide (added as a hot saturated aqueous solution) in dimethyl ...
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1answer
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How long would it take for sucrose to undergo hydrolysis in boiling water?

I was reading the book Cocktail Codex and there was a snippet on avoiding boiling sugar and water to make simple syrup that made me a bit skeptical. Here it is: Heat also affects the molecular ...
10
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4answers
667 views

With which group does the middle oxygen atom of an anhydride remain, on hydrolysis?

With which group does the middle oxygen atom of an anhydride remain, on hydrolysis? As an example, let us say we have the following modification of ethanoic methanoic anhydride, with the middle oxygen ...
9
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Why is ATP, but not ADP or AMP, a sole source of energy?

Why are three phosphate groups (such as in ATP) required for release of energy, but not two (ADP) or one (AMP) phosphates? How does breaking the phosphate bond release energy?
8
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1answer
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How come the same reaction can be balanced in two distinct ways?

I faced this reaction which can be balanced in $2$ distinct ways which are not multiples of each other. $$\begin{align}\ce{6XeF4 + 12H2O &-> 2XeO3 + 24HF + 4Xe + 3O2}\tag{1}\\[0.4em] \ce{4XeF4 ...
7
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4answers
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What an aqueous solution really contains?

I want to know what an aqueous solution is. For example, let's consider a $1~\mathrm{M}$ aqueous solution of $\ce{MgCl2}$. Does it also contain $\ce{MgOH2}$? Though it is a simple question, I feel it ...
7
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1answer
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Comparing the Lewis acidity of carbon tetrafluoride and silicon tetrafluoride

I've been asked to compare the relative acidity of $\ce{CF4}$ and $\ce{SiF4}$. As both atoms have noble gas configurations, neither can act as a lewis acid and so I assume the question is inferring ...
7
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1answer
572 views

Relative rate of hydrolysis of the carbon chlorine bond in thioethers and ethers

I am solving problems based on rates of hydrolysis of compounds but I don't have a general approach to such questions. Which of the following compounds undergoes hydrolysis faster than the second ...
7
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1answer
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Hydrolysis products of chlorides of group 15

$\ce{NCl3}$ on hydrolysis produces $\ce{NH4OH}$ and $\ce{HOCl}$. $\ce{PCl_3}$ when hydrolyzed produces $\ce{P(OH)3}$ i.e. $\ce{H3PO3}$. $\ce{AsCl_3}$ when hydrolyzed produces $\ce{As(OH)3}$. ...
6
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3answers
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Is magnesium sulfate basic, neutral or acidic?

A question in my college test was whether $\ce{MgSO4}$ is neutral, acidic or basic. I was told to solve this kind of problem by hydrolyzing any ions that do not "come from" a strong acid or a strong ...
6
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2answers
7k views

Why can NCl3 be hydrolyzed but CCl4 cannot?

While explaining why $\ce{CCl4}$ cannot be hydrolyzed, we say carbon atom doesn't have any d-orbitals and therefore a water molecule (lone pair electrons of $\ce{O}$ atom) cannot form coordinate bond ...
6
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1answer
608 views

steam distillation of 4-bromoaniline , why render it basic prior

In the multistage synthesis of 4-bromobenzenamine, why must the solution be rendered alkaline prior to the steam distillation after the hydrolysis of 4-bromo-N-ethanoylbenzenamine?
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4answers
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Unexpected reaction during acid hydrolysis of cellulose

Recently I tried to hydrolyze some cellulose: I added some acid to it ($\ce{H2SO4}$) then noticed nothing. Even after a few days there was no visible change and after doing some tests for glucose, ...
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Slow acidification process

I'm trying to find a substitute of Glucono delta-lactone (GDL). This food additive is usually used to produce silk tofu. Because of its slow hydrolysis the pH decreases very smoothly, which results in ...
4
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3answers
594 views

Rates of hydrolysis in bicyclic and monocyclic compounds

Which of the following compounds, 1-bromo-1-methylcyclohexane 1 or 1-bromobicyclo[2.2.2]octane 2, hydrolyzes faster (under comparable conditions)? It may be acid catalyzed or base catalyzed hydrolysis,...
4
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1answer
786 views

Is (high) pressure required to form (quartz) crystals?

I've been reading a lot of sources about the hydrothermal synthesis of quartz using autoclaves. I want to try doing this myself, but before I can I need to know the minimum pressure required. If you ...
4
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1answer
822 views

Which side of the C-o-C bond breaks in esters?

When an ester undergoes hydrolysis which side of the C-O-C breaks for instance in the following example: I believe the first is correct but is it a rule that the salt of a carboxylic acid is formed (...
4
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1answer
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Mechanism for hydrolysis of enol ether to aldehyde

I'm fairly confident in my answers for steps 1-3, but I am not certain how to have the methyl group bonded that is bonded to the alkene carbon leave in step 5 without forming methanol. Here is what I ...
4
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1answer
2k views

How to remove sulfuric acid from sample

I have problem with my experiment. My experiment is acid hydrolysis of ethyl benzoate. The acid that I used is sulfuric acid. My problem is when I get the precipitate (impure benzoic acid) I have to ...
4
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2answers
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Why does sodium react with water to produce a hydroxide, while zinc produces an oxide?

Sodium belongs to the so-called active metals and produces a hydroxide on contact with water. Zinc produces an oxide. Why is it so? I was given a hint: to read up about electrochemical series. I've ...
4
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1answer
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A problem in solubility of salts with multistep hydrolysis of an ion possible

Calculate the solubility of $\ce{MnS}$ in pure water, $K_\mathrm{sp}(\ce{MnS}) = \pu{2.5e-10}$. Assume hydrolysis of $\ce{S^2-}$ ion. $K_1$ and $K_2$ for $\ce{H2S}$ are $10^{-7}$ and $10^{-14}$, ...
4
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1answer
587 views

Hydrolysis of vinyl bromide vs alkyl chloride

Which of the following compounds, 1-bromocyclopent-1-ene 1 or chlorocyclopentane 2, hydrolyses faster than the second under comparable conditions? It may be acid catalysed or base catalyzed hydrolysis ...
4
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1answer
86 views

Mechanism of Acid Hydrolysis

I wanted to ask a question about acid catalysed hydrolysis. I learnt in an introductory course to Physical Organic Chemistry that there are different ways that an ester can be hydrolysed acidically: ...
4
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1answer
317 views

Hydrolysis of an ester

An organic compound X of formula $\ce{C5H10O2}$ forms two compounds when boiled in aqueous sodium hydroxide solution. One of these compounds forms a ketone when treated with acidified potassium ...
4
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1answer
718 views

Hydrolysis of salts containing amphiprotic anion

I am trying to understand the derivation of pH of salt containing amphiprotic anions, but I am facing some difficulty: Ionisation: $\ce{HCO3^- + H2O <=> CO3^2- + H3O+};\quad K_\mathrm{a_2}...
4
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2answers
263 views

Does the salinity in seawater affect the process of alkaline hydrolysis?

I am an architecture student doing a project on crematorium spaces. I am looking at resomation or alkaline hydrolysis as an alternative method of disposition of a body. From what I gather from ...
3
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3answers
575 views

Why does dissolving a salt in water get a high pH?

I dissolved some sodium carbonate in water and I measured the $\mathrm{pH}$. It turned out to be 11. I don't really understand why dissolving it in water increased the $\mathrm{pH}$. I mean, I know ...
3
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1answer
688 views

USNCO question - Finding pH of salt solution from pKa of its parent acid

The question from 2017 USNCO is as below: What is the $\mathrm{pH}$ of a $\pu{0.25 M}$ solution of $\ce{NaCN}$? (The $\mathrm{p}K_\mathrm{a}$ of $\ce{HCN}$ is $9.21$.) (A) $4.91$ (B) $8.61$ ...
3
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1answer
452 views

Hydrolysis of β-1,2 glycosidic bond

Are there any easy, not enzymatic, ways to hydrolyse $\beta$-1,2 glycosidic bonds like they occur in steviosids? I thought of something like vinegar, which is commonly used to cleave the $\alpha$-1,...
3
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1answer
9k views

What exactly is hydrolysis reaction in organic chemistry?What mechanism does it follow?

According to my study material: Hydrolysis is a special type of nucleophilic substitution ($\mathrm{S_N1}$) where water acts as both nucleophile and a solvent molecule. Is this definition correct? ...
3
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2answers
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Acetone absorbing water from the air

Our company uses acetone and isopropanol in our manufacturing process to clean our product. Our operators get the chemicals from a large container and put it into small containers like this (http://...
3
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2answers
13k views

Why is HCl used in hydrolysis of sucrose?

I am aware that $\ce{HCl}$ can be used to help speed up the hydrolysis of sucrose but I haven't really been able to find out why. I've read somewhere that the glycosidic link in sucrose is broken off ...
3
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1answer
86 views

Will PAEK polymers hydrolyze in concentrated sulfuric acid?

One of my duties at the company where I work is to perform intrinsic viscosity (IV) experiments on PAEK (poly(aryl ether ketone)) polymers. These polymers don't dissolve well in most solvents, so the ...
3
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1answer
5k views

Why doesn't NF₃ undergo hydrolysis?

I was reading Jan's answer to the following question-: Why can NCl3 be hydrolyzed but CCl4 cannot? Since nitrogen is less electronegative than fluorine, in NF3 the electrophilic site is the Nitrogen ...
3
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1answer
145 views

Hydrolysing large molecules to reveal amino acids

Consider Oxytocin: I am asked to hydrolyse Oxytocin and reveal 5 amino acids which are the result of this hydrolysis. I must admit I have no idea where to begin. I know that generally amino acids ...
3
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1answer
213 views

Rate of hydrolysis of silicon tetrahalides

Concise Inorganic Chemistry for JEE(Main and Advanced) by JD Lee(Third Edition) writes If we compare the rate of hydrolysis for $\ce{SiX4}$(where X= F,Cl,Br,I), it is in the same order as that of ...
3
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1answer
175 views

Alkylating agent to produce methanol

I was just working though some simple organic problems and came across the reaction of dimethyl sulfate with water to yield methanol. I was curious how that works as $\ce{H2O}$ isn't a strong ...
3
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1answer
3k views

How is it possible, that the hydrolysis of ethers proceed via a SN2 mechanism?

Ethers on hydrolysis with dilute $\ce{H2SO4}$ under pressure produce alcohols. This is basically a type of acidic cleavage of ethers by the SN2 mechanism. (source) There is inversion of ...
2
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1answer
48 views

Hydrolysing a compound by repeated methyl and hydride shifts

The question is to predict the major product in the following reaction. First of all the proton will abstract the bromide ion resulting in the formation of a primary carbocation which being unstable ...
2
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2answers
5k views

How does alkaline hydrolysis of peptides occur?

I have been learning about zwitterions and the isoelectric point, and have been trying to apply this to hydrolysis of peptides. From the diagram in my textbook, I can see that when acid hydrolysis ...
2
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1answer
78 views

Hydrolysis under basic medium

The first compound is said to be hydrolyzed more easily than the 2nd compound below under Alkaline medium . How is this possible ? I thought due to resonance, -NO2 acquires negative charge which ...
2
votes
1answer
636 views

Why are silyl chlorides more readily hydrolysed than alkyl chlorides?

I know that the $\ce{Si-Cl}$ bond has a slightly higher energy, but silyl chlorides are much more readily hydrolyzed compared to alkyl chlorides. I do not fully understand why that is. My thoughts so ...
2
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1answer
306 views

Does evaporation reverse salt hydrolysis?

It has been a long time since I studied organic chemistry, but one thing I do remember is that when we needed cyanide salts we were told not to bother keeping any remaining solution because the salts ...
2
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1answer
50 views

Reversablity of dehydration

Aqueous magnesium bicarbonate when evaporated decomposes into magnesium carbonate. Is that reaction reversible by dissolving the carbonate in soda water?
2
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1answer
442 views

Why is the hydrolysis of the conjugate base of a weak acid neglected in buffer solutions?

Consider a solution which contains a weak acid and the salt of its conjugate base with a strong base. e.g. $$\ce{CH3COOH + H2O <=>[$K_\rm{a}$] CH3COO- + H3O+}\tag1$$ $$\ce{CH3COO- + H2O <=&...
2
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0answers
55 views

Hydrolysis of an amidine derivative under acidic conditions

I know that an imine can undergo acid hydrolysis to yield a corresponding amide: https://chem.libretexts.org/@api/deki/files/13283/10.jpg?revision=1 But I am looking at a mechanism for acid ...
2
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0answers
27 views

Phosphonate reaction with oxides and their stability?

I have read some papers stating that $\ce{SiO2}$ surfaces can bind phosphonates, but in water they hydrolyse. However, for $\ce{Si}$ surfaces, they are stable in water. In both cases, the reaction ...
2
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0answers
108 views

Why does water electrolysis use direct current?

Every source I've found regarding water electrolysis says that it's done using direct current (rather than alternating current), but I haven't found a single source that mentions why. Obviously, ...
2
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0answers
390 views

proteolysis - how to determine the partial or completeness of the cleavage reaction?

Though the question is about biomolecules, we agree the underlying functions, formation, degradation etc come down to chemistry, (then physics and maths). I am posting it here to receive an ...