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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Flash point change of Ethanol Water mixture [closed]
As all of us know practically that pouring more water in an Ethanol Water mixture means that it makes a higher flash point of the mixture.
What is the chemical reason behind it? why does it not reach ...
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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 ...
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$\ce{C2H5ONa ->[CH3I] ?}$ [closed]
Product C in the reaction
$$\ce{C2H5Br ->[NaOH][aqueous] A ->[Na] B ->[CH3I]C}$$
will be:
(a) propane
(b) ethyl iodide
(c) ethane
(d) ethyl methyl ether
What is product C?
A is $\ce{C2H5OH}$...
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Can the reactivity of ethanol, ethanal, and ethanoic acid be related to its toxicity?
Ethanal (acetaldehyde) is more toxic than ethanoic acid (acetic acid) which is more toxic than ethanol (drinking alcohol).
0.7 ethanal LD50 oral g/kg
3 ethanoic acid
7 ethanol
Can this be explained ...
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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 $20^{\circ}C$). ...
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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 ...
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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 ...
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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 ...
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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 ...
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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, ...
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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-...
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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 ...
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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 ...
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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 ...
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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 ...
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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?
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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, ...
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Ion from unsaturated ether
As far as I am concerned, from unsaturated primary/secondary amines (enamines) we obtain imines, like we do obtain carbonyls from enols, by tautomerism. For tertiary enamines, we have a corresponding ...
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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 ...
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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 ...
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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 ...
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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 ...
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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 ...
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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 ...
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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?
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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?
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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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Halogenation by Phosphorous tribromide vs using HBr
My textbook introduced $\ce{PBr3}$ by stating that it leads to an inversion in stereochemistry since it always goes through an SN2 pathway, unlike using $\ce{HBr}$.
My question is that since $\ce{Br-}$...
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Why is the melting point of tert-butyl alcohol 140 °C higher than that of sec-butyl alcohol?
This is one of the most drastic differences in a physical property I've ever seen for two such similar molecules, and in a simplistic sense anyway the difference lies in the opposite direction from ...
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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 ...
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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 ...
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Why don't secondary alcohols react with HBr/HI via SN2?
In polar protic solvents, $\ce{Br-}$ and $\ce{I-}$ are considered to be very good nucleophiles. Now, here the solvent is alcohol which is polar protic. So, why don't secondary alcohols react with $\ce{...
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Why is ethanol distilled off before adding water in the first step of a malonic synthesis?
I am doing a malonic synthesis shown below, and I wonder why I should distill ethanol off before adding water in the first step of the reaction (First I add absolute ethanol and solid sodium).
CommunityBot
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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.
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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 (...
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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 ...
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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 ...
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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 ...
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Are allylic tertiary alcohols oxidized by the Jones' reagent via a classical carbocation intermediate?
I know the mechanism for Jones' oxidation is (picture from Organic Chemistry by Clayden):
and it proceeds through a chromate ester. And in general we understand that the Jones' reagent $\ce{H2CrO4}$ ...
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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 ...
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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"
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Solubility comparison of hexan-1-ol and cyclohexanol in water
Is hexan-1-ol or cyclohexanol more soluble in water? The answer is supposedly cyclohexanol. However, I found a statement in a book:
Isomeric alcohols have solubilities in the order: primary alcohol ...
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Why can unsymmetrical tert-butyl ethers be prepared by dehydration of the constituent alcohols?
Practice problem 11.11 what stops R-O-R from forming at the same rate as the desired product?
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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 ...
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When does reaction of alcohol with alumina give an ether and when an alkene?
What is the main product when an excess of ethyl alcohol vapour is passed over heated alumina at 250 °C?
I read that this reaction gives an ether (here, diethyl ether) at relatively lower temperature ...
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Why does the reaction of the primary alcohol cyclopentylmethanol with hydrogen bromide follow SN1 mechanism?
Example 2: Identify all the products formed in the following reaction and indicate the major product.
Solution: Three products will be formed in the given reaction as shown below:
In this reaction ...
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Reaction between 1,2-bis(buta-1,3-dien-1-yl)cyclohexan-1-ol and potassium hydride in THF
Which product is formed in the following reaction?
I am quite certain that we deal with an oxy-Cope rearrangement that works at room temperature, but I don’t know how to draw the product given the ...
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Why n-butanol is not used as a safer alternative to ethanol in the alcoholic beverages?
The LD50 of n-butanol adjusted for its intoxicating potency is about 1.5 times that of ethanol. This would mean to me that n-butanol is therefore 50 % safer than ethanol. Why is it not used to replace ...
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How is the intermediate compound 2-chloropropan-1,3-diol is formed when hypochlorous acid is added to allyl alcohol in the preparation of glycerol?
The expected product is 3-chloropropan-1,2-diol since secondary carbocation is more stable than primary but it is not formed.
I have surfed the internet a lot regarding this and none seems to be a ...
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Correction formula for alcoholmeter
I need to find the formula, if there is one, which would calculate the correction of alcoholmeter.
Basically convert observed %ABV (Alcohol by volume) to actual %ABV using the sample's temperature.
...
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