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28 votes
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What chemical properties of ethanol make it usable for drinks as compared to that of methanol?

The problem arises from the metabolized products of methanol. Methanol oxidizes in the liver by an enzyme called alcohol dehydrogenase to formaldehyde which is further metabolized to formic acid by ...
Nilay Ghosh's user avatar
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22 votes
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Un-denaturing industrial alcohol

(I'm no chemist, but here's my take on it) Let's see: I’m an alcoholic, and I really hate having to dole out large amounts of cash to purchase your usual "drinking"-ethanol. So I get this amazing ...
paracetamol's user avatar
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21 votes

When I burn isopropyl alcohol (IPA), it burns orange. But when I burn ethyl alcohol, it burns totally blue. Why is this?

IPA has a different carbon:hydrogen ratio than ethanol. There is more incomplete combustion occurring with IPA, hence the smoky orange flame and smell of soot. Ethanol combusts more completely, ...
arevmelikyan's user avatar
21 votes

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

According to the metabocard at HMDB — Nitroglycerin, nitroglycerin is only found in individuals that have used or taken this drug. No known metabolic pathways for glycerin lead to nitroglycerin either....
andselisk's user avatar
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19 votes
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Ring contraction in pinacol rearrangement of cyclohexane-1,2-diol

Background You don't specify whether we are starting with cis- or trans-cyclohexane-1,2-diol, but it doesn't matter since both isomers will interconvert under the reaction conditions. Therefore we ...
ron's user avatar
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18 votes
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Why do hydroxyl groups only produce a singlet in proton NMR?

You are both right and wrong. At low temperatures, the NMR spectrum will indeed be as you predicted: the $\ce{H}$ from $\ce{OH}$ will produce a quartet and likewise the $\ce{H}$ from $\ce{CH_3}$ will ...
Hippalectryon's user avatar
18 votes

Why is thionyl chloride preferred for preparing alkyl chlorides from alcohols?

Preparation of alkyl chlorides from alcohols by thionyl chloride is preferred over other methods mentioned because of the following reasons : $$\ce{R-OH + PCl5 → R-Cl + POCl3 + HCl ↑}$$ $$\ce{...
Resorcinol's user avatar
  • 1,439
18 votes
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When I burn isopropyl alcohol (IPA), it burns orange. But when I burn ethyl alcohol, it burns totally blue. Why is this?

Interesting observation. The blue flame color of all hydrocarbon fuels is due to the emission small diatomic carbon species such $C_2$ or CH. There is nothing magical about IPA having a yellow flame. ...
AChem's user avatar
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17 votes
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Why is thionyl chloride preferred for preparing alkyl chlorides from alcohols?

Thionyl chloride is preferred for preparing alkyl chlorides from alcohols because the by-products formed in the reaction are $\ce{SO2}$ and $\ce{HCl}$ which are in gaseous form and escape into the ...
Vishnu JK's user avatar
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17 votes
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Is it correct to say that ethenol is an alcohol?

The golden book states that ethenol is an alcohol: Enols Alkenols; the term refers specifically to vinylic alcohols, which have the structure $\ce{HOCR'=CR2}$. However, the modifier "vinylic"...
TAR86's user avatar
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17 votes
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What happens if you carbonate ethanol?

Carbon dioxide is in fact roughly ten times as soluble in ethanol as in water [1](https://doi.org/10.1016/j.fluid.2006.04.017) (meaning you need more dissolved under pressure to get that bubbling ...
Oscar Lanzi's user avatar
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16 votes
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What is the name origin of ester?

The term "Essigäther" is actually the German name for ethyl acetate i.e Essig = "vinegar" + Äther = "ether". "vinegar" becomes acetic, hence ethyl acetate ...
Nilay Ghosh's user avatar
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14 votes
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Are there ethanol and methanol analogues with more than one hydroxyl group?

Generally speaking, they're called diols when bearing two hydroxyl groups. If they're on the same C, this is called a geminal diol, if they are on neighboring Cs, they're called vicinal diols. The C ...
user1573870's user avatar
13 votes

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

I have not written the steps for carbocation formation, simple dehydration.
Avyansh Katiyar's user avatar
12 votes
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Formation of toluene from (cyclobutane-1,2,3-triyl)trimethanol using conc. sulphuric acid

Seeing the reaction given here, I assume that is an on-paper reaction that takes place and that all three alcoholic groups are dehydrated. The mechanism (on paper) seems to be as follows Dehydration $...
Safdar Faisal's user avatar
11 votes

Is sodium borohydride really a better base than an alcohol?

General considerations It’s not the basicity that is the important factor here, it is the nucleophilicity. The hydride ion, whether present as tetrahydridoborate or as a lone hydride is a very lousy ...
Jan's user avatar
  • 68.2k
11 votes

Un-denaturing industrial alcohol

The reason criminals don't undenture alcohol is probably because it's cheap and easy to make your own alcohol at home. Plus it's legal in the US (click on G1) and most other English-speaking ...
Jason's user avatar
  • 111
11 votes

Un-denaturing industrial alcohol

In Soviet Russia, where alcoholism was widespread and homebrewing illegal, undenaturing alcohol was a pretty common thing - a part of national culture, in a way - along with such practices as: ...
Ivan Neretin's user avatar
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11 votes
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Why can't alcohols form hydrogen-bonded dimers like carboxylic acids?

The strength of a hydrogen bond somewhat depends on the $\ce{X-H\bond{...}X}$ angle that the hydrogen-bonding hydrogen forms with the two electronegative elements $\ce{X}$. In our case, carboxylic ...
Jan's user avatar
  • 68.2k
11 votes
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Why do Grignard reagents add to propargyl alcohols?

The addition of Grignards to propargyl alcohols occurs via the alkoxide salt, after deprotonation:[1] Here: the reactivity may be explained by the stabilising influence of complexation; the ...
orthocresol's user avatar
  • 71.4k
11 votes

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

The addition of a Grignard to a carbonyl doesn't form an alcohol—not directly at least. It forms an alkoxide ion (i.e. the conjugate base of an alcohol). Only when that reaction is complete, is water (...
orthocresol's user avatar
  • 71.4k
11 votes

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

First of all, you don't need to eat soap to get glycerin in your system. Fats are broken down by digestion into glycerin and fatty acids. Glycerin is also available commercially as a cough syrup and ...
Level River St's user avatar
10 votes
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Producing ketones from secondary alcohols using hydrogen peroxide

I think it is possible to use hydrogen peroxide. This paper discusses it: http://greenchem.uoregon.edu/PDFs/ResourceID88.pdf Other alternatives: Pyridinium Chlorochromate (or PCC for short) Dess-...
getafix's user avatar
  • 8,495
10 votes
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Is methanol really more acidic than water?

First, water’s $\mathrm{p}K_\mathrm{a}$ in water is $14$ as explained here. This means that $\ce{H2O}$ is slightly dissociated in liquid form, such that $[\ce{H+}] = [\ce{HO-}] = 10^{-7}$. Second, I ...
SCH's user avatar
  • 772
10 votes

How to convert ethanol to benzoic acid?

Here is how I would do it. Part I: Blue First, ethanol 1 is oxidised to acetaldehyde 2, which undergoes nucleophilic addition with $\ce{KCN}$ and $\ce{HCN}$ to form the hydroxynitrile 3, and finally ...
Linus Choy's user avatar
10 votes

Does benzene react with steam to create an alcohol?

Strange as it may seem, benzene can be reacted with steam over a suitable catalyst [1]. The result is a complete breakdown to simpler molecules like methane and carbon dioxide. Typical conditions ...
Oscar Lanzi's user avatar
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10 votes
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Is Pinacol rearrangement the source for the ring expansion?

Your first and third structures are good but the arrow pushing in the second structure doesn't get the job done. As you have noted, diol 1 forms carbocation 2a the more stable of the two options. Now ...
user55119's user avatar
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10 votes
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Do amines or alcohols have stronger intermolecular hydrogen bonds?

The boiling point of non-ionic compounds are highly depend on their H-bonding abilities. For example, boiling point of water (molar mass: $\pu{18.02 g/mol}$) is $\pu{100 ^\circ C}$ at $\pu{1 atm}$ ...
Mathew Mahindaratne's user avatar
10 votes

Do amines or alcohols have stronger intermolecular hydrogen bonds?

Mathew Mahindaratne has provided analysis based on experimental values of the boiling points of the two compounds. I would like to offer a different view using bonding analysis. Before I begin ...
Tan Yong Boon's user avatar
10 votes

Identification of the organic compound

The given answer is wrong in many ways: 4 did not satisfy both criteria C and E, because it is not a chiral compound to begin with. 10 did not satisfy the criteria D, because it does give a ...
Mathew Mahindaratne's user avatar

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