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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Why is the boiling point of alcohols primary > secondary > tertiary? [duplicate]

If I have 1-butanol, 2-butanol, and 2-methyl-2-propanol, the boiling points of each are 117, 99, and 82 degrees Celsius, respectively. Why does that happen knowing that all of them have the same ...
-4 votes
2 answers
40 views

Ethanol Interactions

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 ...
-4 votes
0 answers
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Rust inhibitor for methanol solution [closed]

What product or additive will work as a rust inhibitor when mixed into a methanol/water solution?
-2 votes
0 answers
32 views

How to get isopropyl alcohol residue off of license plate [closed]

License plate is aluminum with a painted/printed glossy finish. I got glue all over it and used isopropyl alcohol to clean it off. It left the finish all smeared and cloudy. Is there any way to get ...
1 vote
1 answer
5k views

Mechanism of reaction of alcohol with NaBr + H2SO4

My teacher told that the mechanism for reaction of alcohol with $\ce{NaBr + H2SO4}$ follows SN1 when alcohol is 2°/3° and SN2 when it is primary or methanol. He told that the reactivity of alcohol ...
2 votes
0 answers
103 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 ...
1 vote
1 answer
133 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* ...
1 vote
0 answers
59 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 ...
-1 votes
1 answer
85 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.
-4 votes
1 answer
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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 $\ce{Ph-CH2-CH2-CH2-OH}$ $...
5 votes
1 answer
351 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 ...
4 votes
3 answers
830 views

The intrinsic electron-withdrawing nature of alkyl groups

What you are about to read may be a very mind-boggling paragraph but please do not regard it as nonsense. Please think through it thoroughly. In Chapter 6 of Organic Chemistry (4th ed.) by Maitland ...
0 votes
0 answers
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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 ...
-1 votes
1 answer
63 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 ...
2 votes
0 answers
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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 ...
3 votes
0 answers
64 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 ...
-2 votes
1 answer
46 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 ...
8 votes
2 answers
3k views

Saturation of multiple solutes

Can a liquid which is saturated with a single solute, dissolve a different solute, or is saturation a universal thing? I ask because I’ve seen that different solutes have different points (amounts) at ...
0 votes
0 answers
512 views

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 ...
-1 votes
1 answer
123 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 ...
-4 votes
1 answer
93 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 ?
7 votes
2 answers
3k views

Benzene from cyclopropane-1,2,3-triyltrimethanol in acidic medium

What is the mechanism of the conversion of cyclopropane-1,2,3-triyltrimethanol to benzene in in acidic medium? After performing E1 thrice I was expecting 1,2,3-trimethylidenecyclopropane to form ...
0 votes
1 answer
256 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 ...
8 votes
0 answers
224 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 ...
-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} ...
2 votes
0 answers
93 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 ...
19 votes
5 answers
14k views

Un-denaturing industrial alcohol

I have a question regarding the denaturation of industrial ethanol with methanol to discourage its consumption. The boiling point of methanol is 64.7 °C, while the boiling point of ethanol is 78.37 °...
3 votes
1 answer
270 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 ...
0 votes
1 answer
425 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 ...
4 votes
3 answers
635 views

Is the negative excess volume of ethanol/water the cause of my math error?

I have a binary mixture, say ethanol at $90\%wt$ ethanol, $10\%wt$ water. According to Perry's Chemical Engineers' Handbook 9th Ed., that mixture has a density of $0.81797g/cc$ (at $20^{\circ}C$). ...
2 votes
0 answers
90 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 ...
3 votes
1 answer
1k views

Does yeast, sugar and water really produce any noticable/significant amounts of methanol?

I just read this question on Quora about distilling during pre-industrial age, which reminded me about multiple discussions I have heard or read during the years about whether the fermentation process ...
6 votes
1 answer
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Protonation of tetrahydrofurfuryl alcohol

I think the ethereal oxygen in THFA gets protonated. Due to greater +I effect, the electron density on it is higher, hence it is more likely to behave as a Lewis base. Consequently, the product formed ...
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, ...
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-...
6 votes
1 answer
230 views

Acidity of alcohols

So everywhere that I've read, there's the reasoning that the acidity of a compound is determined by how stable the conjugate base is, this should be the same for alcohols too, but on Chemistry ...
-2 votes
1 answer
679 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 ...
4 votes
2 answers
762 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 ...
15 votes
4 answers
40k views

Why does alcohol crack acrylic (plexiglass)?

I have seen videos and discussions about alcohol cracking acrylic, and waterblock manufacturers reminding users to not use alcohol in cooling systems with plexiglass acrylic, but why is this so? The ...
-1 votes
1 answer
512 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?
-1 votes
1 answer
73 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, ...
7 votes
1 answer
287 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 ...
2 votes
2 answers
304 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 ...
5 votes
1 answer
406 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 ...
12 votes
3 answers
13k views

Why do tosylation and mesylation of alcohols follow different mechanisms?

Why do the tosylation and mesylation of an alcohol proceed via different mechanisms? More specifically, In tosylation, the lone pair of the alcohol attacks the sulfur in TsCl, but why does it not ...
0 votes
1 answer
614 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 ...
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 ...
4 votes
2 answers
1k views

What is the mechanism for the oxidation of a lactol to a lactone?

Recently, I came to know that lactols can be converted to lactones but I wasn't able to find the suitable reagent and the reaction mechanism. Can someone elaborate the same?
4 votes
2 answers
8k views

Converting methanol into methane

I know that methane to methanol is a common practice, but is it possible to convert methanol back into methane, and would it be a relatively easy process to achieve?
4 votes
2 answers
363 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 ...

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