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Questions tagged [alcohols]

For questions about saturated and unsaturated alcohols, their physical properties, their reactions, etc. For questions about phenol, use the [phenols] tag instead.

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What does phosphorodibromidous acid do in solution?

When tribromophosphine is used to activate an OH to enable its substitution, the leaving group is listed by PubChem as "phosphorodibromidous acid" and doesn't seem to really exist from a ...
trerri's user avatar
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1 vote
1 answer
62 views

Dehydration of isoborneol with carbocation rearrangement

What rearrangement happens when isoborneol (structure below) is heated with acid? Since acid is used and the hydroxyl group is present, the reaction mechanism is dehydration. My attempt: In the ...
Bongo Man's user avatar
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3 votes
1 answer
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Why is there a [M-1]+ in lieu of a parent signal in the Mass Spectrometry of Primary Alcohol Chains?

I have looked virtually everywhere for an explanation of why alcohols EI GC-MS always have a more prominent M-1 signal over a Parent chain signal--sometimes no parent signal at all. One site says http:...
James Perrin's user avatar
0 votes
0 answers
15 views

Reaction of CH3NH2 (Excess) with NaNO2+HCl [duplicate]

I was told by my chemistry instructor that if we react excess CH3NH2 with NaNO2+HCl(source of HNO2), an ester is formed due to further dehydrogenation of methanol formed by HCl.Im having trouble ...
Lucifer Flux's user avatar
11 votes
2 answers
3k views

Is nitroglycerin synthesis within human digestive system from eating soap possible?

Could you make nitroglycerin by eating large quantities of pure glycerine soap? A quick google search told me flatus are 59% nitrogen, but I couldn't find anyone else with my exact question (which ...
Ivory427e's user avatar
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0 votes
2 answers
82 views

What exactly does 'isomerism' mean?

Today, I was confronted with this question - Is 2-methylpenten-3-one an isomer of 5-hexen-1-ol? Some people say yes; while some say otherwise. I'll put forward the logic on both sides. The side of ...
ChemGeek007's user avatar
-3 votes
1 answer
34 views

ease of dehydration [closed]

ease of dehydration for the following alcohols is? I understand the most easiest would be for III, but shouldn't it be easier for I than for II? because II forms an anti aromatic compound? But the ...
user145228's user avatar
-4 votes
2 answers
45 views

Ethanol Interactions [closed]

I would like to know if anyone is aware of any substance which, when it interactives with alcohol (ethanol), and is consumed, changes the taste of the alcohol (negatively) and/or induces sickness in ...
J Cunningham's user avatar
2 votes
0 answers
117 views

Removing DCC and its by-product from Steglich Esterfication

In my small research, I want to synthesize 3 alkyl gallates (ethyl gallate, butyl gallate, and hexyl gallate), and here's my overall reaction using Steglich esterification): However, from reading ...
Jonathan's user avatar
  • 155
1 vote
0 answers
63 views

Can I make an alcohol-based stain from a pigment with an alkaline extraction process?

I'm in a situation where I don't really even know enough to know if what I want makes sense or has the kinds of problems that I think it might have, but here's the situation: I would like to make a ...
nyckarna's user avatar
-1 votes
1 answer
94 views

What is the pKa of choline chloride?

I am looking for the pKa of choline chloride, which should be higher than 7 (around 10?), but I cannot find any reference value.
David Moldes's user avatar
-4 votes
1 answer
58 views

What shold be the answer to the given reaction? [closed]

Q.75 The final product A, formed in the following reaction sequence is: $$\ce{ Ph-CH=CH2 ->[(i) BH3 (ii) H2O2,OH- (iii) HBr][(iv) Mg, ether, then HCHO/H3O+] A }$$ Options $\ce{Ph-CH2-CH2-CH2-OH}$ $...
Rock's user avatar
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5 votes
1 answer
393 views

Using Thionyl Chloride with tertiary alcohol

I have a question regarding using $\ce{SOCl2}$ to convert an alcohol into a alkyl halide. The Klein book mentions that $\ce{SOCl2}$ is only used for primary and secondary alcohol; however, in the ...
Jaehyun Ahn's user avatar
0 votes
0 answers
36 views

Effect of Steric Hindrance in Pinacol-Pinacolone Rearrangement

In the acid catalysed rearrangement of vicinal diols to carbonyl compounds which is pinacol-pinacole rearrangement, The migratory order of the groups is H>Aryl>Alkyl My question is that how aryl ...
Abhinav's user avatar
-1 votes
1 answer
65 views

Alcohol preparation process

Currently Studying in high school, I encountered a reaction in organic chemistry. I got a reaction in which alcohol(ethanol) was dehydrated to form unsaturated hydrocarbon(ethene) and water. I wanted ...
Abhay Pratap's user avatar
2 votes
0 answers
26 views

Creation of a Solution of Liquid Latex + Sodium Caseinate with Polyvinyl Alcohol

I am going to be experimenting with creating different types of liquid latex formulations, primarily for the purposes of increasing shear strength and tear resistance, as well as just general ...
Varstraypl's user avatar
3 votes
0 answers
70 views

Boiling point of pentanol isomers

Arrange the following alchohols and alkanes in increasing order of boiling point: 3-pentanol, n-pentane, 2,2-dimethylpropanol, n-pentanol I understand that n-pentane would have the lowest boiling ...
calcandquant's user avatar
-2 votes
1 answer
50 views

Can I make orthophosphoric acid from sodium dihydrogen phosphate and an acid which I can use to make ethyl iodide?

For my project I needed to di-substitute benzamide with ethyl group at N position to create DEB as a mosquito repellent. The first part of creating benzamide I was able to do, but the second part of ...
N N-DiEthyl Benzamide's user avatar
1 vote
1 answer
145 views

What is the rate of hydration in the following compounds

I came across a question : What is the order of rate of hydration in the following compounds: My attempt to this question was checking the stability of carbocation. As III has a possibility of 3* ...
Ash_Tag's user avatar
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0 answers
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What mechanism do reaction of PCl5 follows, SNi or SN2?

I was taught that $\ce{PCl5}$ reacts with alcohols by $S_Ni$ mechanism as shown below: Here it can be seen that $\ce{PCl5}$ exists as $\ce{[PCl4]+[PCl6]-}$ and so lone pair of the alcohol is donated ...
D13G's user avatar
  • 89
-4 votes
1 answer
96 views

Make ethanol with sourdough [closed]

I have seen a lot of videos on internet and to make ethanol they ferment sugar with yeast but is it possible to ferment sugar using sourdough ?
goAT2160's user avatar
-1 votes
1 answer
132 views

Why is there difference in reactions in alcoholic and aqueous medium while both are polar protic solvents?

We use an alcoholic medium for reactions in which we want to prevent the characteristics of the anionic species and an aqueous medium for the reactions in which we want to control the activity of the ...
D13G's user avatar
  • 89
0 votes
1 answer
284 views

Why does brandy have a higher methanol-to-ethanol ratio than beer, despite the distillation?

From my googling, beer tends to contain around 16mg/L of methanol. While for brandy, typical methanol content is around 1000mg/L (give or take a factor of 3, depending) The distillation that brandy ...
MWB's user avatar
  • 519
-5 votes
1 answer
77 views

Can diols be oxidised to hydroxyacids? [closed]

Conversion of ethanol to ethanoic acid $ \ce{CH3CH2OH_{(aq)} \xrightarrow[KMnO^{-}_{4}]{NaOH} CH3CHO_{(aq)} + H2O_{(l)} }\\ $ $\ce{CH3CHO_{(aq)} + H+_{(aq)} \xrightarrow[KMnO^{-}_{4}]{HCl} ...
Nickotine's user avatar
  • 131
2 votes
0 answers
105 views

Predict the products of organic reaction sequence

This is a reaction sequence involving alcohols, phenols, halides, alkenes ,alkanes etc , and the task is to identify all the compounds A to E The few things I was able to identify : The compound C ...
satvik's user avatar
  • 21
3 votes
1 answer
323 views

Why does Alcohol-Dehydrogenase prefer ethanol over methanol?

So I've had this experiment at university, where we tried using (yeast) ADH on different alcohols and measuring which one gets turned over the fastest. We also learned that ADH prefers shorter ...
m0n74g3's user avatar
  • 33
0 votes
1 answer
475 views

How does sodium react with methanol?

Strong acids of $\ce{AH}$ type readily dissociate to its constituent ions (considering the solvent is water): $\ce{A-}$ and $\ce{H+}$. But the mechanism of the reaction between sodium metal and ...
Chesx's user avatar
  • 140
2 votes
0 answers
96 views

Protecting Thiol group in presence of alcohol

What protecting group can I use that will protect the thiol in the presence of an alcohol? Is there a set of conditions, or a group that I can use that is selective to the thiol over the alcohol? I am ...
Maya H's user avatar
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8 votes
0 answers
227 views

Mysterious violet-purple compound in "Gerber Method" & "Banana oil synthesis"

During the determination of fat in milk (Gerber method), in a milk butyrometer are mixed milk + $\ce{H2SO4}$ 90% w/w + isoamyl alcohol (isopentyl alcohol) and heating. The acidic mixture separates ...
Stefano's user avatar
  • 109
0 votes
0 answers
63 views

What would be the correct IUPAC name of this compound? [duplicate]

How many carbon atoms will be there in the parent carbon chain? I have proposed its few names, which one is more appropriate? 4-Chloro-3-ethyl-2-(1-methylethyl)-butan-1-ol 3-(1-Chloromethyl)-2-(1-...
Dheeraj's user avatar
15 votes
1 answer
3k views

What happens if you carbonate ethanol?

The electronics youtuber bigclivedotcom has an on-and-off-again series where he carbonates various types of alcohol and comments on the taste. One thing he's noticed is that the stronger the alcohol, ...
David Given's user avatar
-2 votes
1 answer
745 views

Why does Methanol have a higher surface tension than Ethanol? [closed]

I am researching the surface tension of different alcohols and found something odd: the surface tension of Methanol was higher than that of Ethanol, which doesn't make sense to me. My understanding is ...
Woojin Rho's user avatar
4 votes
2 answers
802 views

Flash point of naptha and propanol

I filled a Zippo lighter with 2-propanol and it lit up easily when the ambient temperature was around 6-7 degrees Celsius. It was impossible to light it up when the temperature was around 3-4 degrees ...
flappix's user avatar
  • 149
-1 votes
1 answer
553 views

reaction of PCl5 with alcohol [closed]

I am able to think of two possible mechanisms for alcohol+PCl5 here, SN1 and SN2. In SN1, Inversion won't occur whereas, in SN2 inversion will occur. Which of the two is correct?
NNG's user avatar
  • 1
-1 votes
1 answer
81 views

Why is Quinone used, while oxidising primary alcohols by Oppenauer Oxidation, instead of Acetone? [closed]

Usually, during Oppenauer Oxidation, while oxidising secondary alcohols, acetone solution is used with Aluminium Tertiary Butoxide. This results into the oxidation of secondary alcohol into a ketone, ...
Enormity's user avatar
7 votes
1 answer
300 views

Why don’t Grignard reagants react with their alcohol products?

I’ve read that Grignard reagants react pretty quickly with alcohols and carboxylic acids to form their respective conjugate bases. I’ve also learned that Grignards can be used for the prepararion of ...
Allie's user avatar
  • 79
2 votes
2 answers
349 views

Protonation in acid-catalyzed nucleophilic attack of alcohol on carbonyl

When studying acid-catalyzed nucleophilic attack of alcohol on carbonyl, I got puzzled by the first protonation step. In textbooks, they often show that the first step is to protonate the carbonyl ...
AlojzyBąbel's user avatar
5 votes
1 answer
435 views

Mechanism for a reaction of reduced fluorophenol with BF3?

In the given question, $\ce{BF3}$ will act as an electrophile. Will it form $\ce{BF4-}$ and leave a positive charge on the carbocation to which $\ce F$ was attached or react with $\ce{OH}$. It will ...
Vansh Bhardwaj's user avatar
0 votes
1 answer
736 views

How did you convert primary alcohol using HCl (with ZnCl2)?

I kinda feel weird for this type of question. When primary OH (alcohol) is converted with HCl (with ZnCl2), how did the free Cl-ion come from? If, it is came from HCl, since when we get rid of the H ...
Nku's user avatar
  • 1
2 votes
0 answers
40 views

Feasibility comparison of symmetric ether synthesis and HCl + alcohol SN2 reactions

According to Solomons & Fryhle 10$^{th}$ edition Ch 11.8, Because the chloride ion is a weaker nucleophile than bromide or iodide ions, hydrogen chloride doesn't react with primary/secondary ...
chemN00b's user avatar
  • 342
4 votes
2 answers
386 views

Why does "bis-tris propane" have two pKa values?

Wikipedia gives two pKa values for "Bis-tris propane". What about bis-tris-propane gives this compound two pKa values where other compounds have only one? How am I to choose which pKa value ...
Nicholas DeMarco's user avatar
2 votes
1 answer
2k views

Can someone explain the chemistry around adding Isopropyl Alcohol to water contaminated gasoline - how does the IPA 'remove' water from the gas?

So there are many products on the market sold as fuel additives; some (like 'Heet' brand) are nothing more than 99.9% isopropyl alcohol in a nice package. When trying to understand how they work and ...
wild coast's user avatar
3 votes
1 answer
305 views

Does the ‘e’ from ‘-yne’ get dropped in compounds of higher functional groups?

What is the way of representing a triple bond in a compound of a higher functional group, like alcohol? Does the ‘e’ from ‘-yne’ get dropped like in the case of the ‘-ene’ suffix? For example, would ...
dotmashrc's user avatar
  • 373
3 votes
0 answers
48 views

How to calculate composition of alcohol/water mixture to achieve given concentration of alcohol vapors in air for calibrating a DIY breathalyzer?

I made a breathalyzer using a MiCS-5524 gas sensor. I would like to calibrate it so it can be close to accurate. e2v technologies — MiCS Application Note 4, Using MiCS Sensors for Alcohol Detection (...
Bill2k's user avatar
  • 31
-2 votes
1 answer
526 views

Oxidation of Methanol - how to write the half reaction

I am trying to write the half reaction equations for: $$\ce{CH3OH + O2 -> HCOOH + H2O}$$ The primary goal for me here is to find out which reactant is oxidising without using prior knowledge of ...
thetrueembodimentofstupidity's user avatar
-1 votes
1 answer
103 views

Why is it not possible for water to directly attach itself to the alkene to form an alcohol in oxymercuration? What is the need for mercuric acetate?

When going through the preparation of alcohols, I came across the method of Oxymercuration-Demercuration. Now, after going over the reaction, I didn't understand the purpose of the mercuric acetate ...
Sahil Muhammed's user avatar
2 votes
0 answers
36 views

Which 1,2-methylene shift is more favourable in ring expansions where ring has substituents

In the above reaction, first the -OH group is protonated after which it leaves creating a carbocation intermediate as shown Now, ring expansion is a more favourable rearrangement, however there is a ...
Pravimish's user avatar
  • 169
2 votes
1 answer
50 views

What's a good high precision analysis technique (after GC) to measure trace isopropanol in water samples?

Looking to measure trace IPA content in water samples. Only GC I have access to doesn't take samples with water. Different columns not an option.
A. Anil's user avatar
  • 31
0 votes
1 answer
122 views

Is formation of cyclic carbonate from trimethyl orthoformate and vicinal aromatic 1,2-diol possible? [closed]

Hello, my question is, "is it possible cyclic carbonate formation between trimethyl orthoformate and vicinal aromatic 1,2-diol"
Sajad Khanlarkhani's user avatar
-1 votes
1 answer
491 views

How is Magnesium Ethoxide appropriately prepared, stored and used to dry ethanol?

I found many procedures vaguely describing the preparation of magnesium ethoxide from elemental magnesium in excess dry ethanol in the presence of I2 as activator (in absence of air), I also know that ...
Hans's user avatar
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