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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40
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1answer
82k views

Differences between phenols and alcohols

I know phenols are more acidic as compared to alcohols, but are they considered different from alcohols? Sure, you can study something as a subset, but are phenols considered a subset of alcohols, or ...
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3answers
58k views

Is alcohol really a solution?

A friend recently sent me the following chemistry joke: As a lover of puns, I'd like to enjoy it, but I think that it is actually false the way it is phrased. A solution is defined as: "a ...
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6answers
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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 °...
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5answers
8k views

Strength of hydrogen bonding in phenol or methanol

I wanted to know whether hydrogen bonding is stronger in phenol or methanol. I saw on Wikipedia about the enthalpies of hydrogen bonding in various cases. but could not find the answer to this ...
16
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3answers
8k views

Why does hand sanitizer turn into a liquid after coming out of the bottle?

Hand sanitizer is a gel in its bottle, but when I pour it on my palm, it turns into a free flowing liquid. Why does that happen? It doesn't turn to a liquid when I pour it on my floor or my table. ...
15
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4answers
22k views

Why is pyridine used when making tosyl esters from alcohols?

Tosyl chloride is used to make a hydroxyl group into a better leaving group. However, when the reaction of tosyl chloride and an alcohol occurs, a weak base such as pyridine should be used. Why?
15
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2answers
69k views

Reaction of alcohols with PCl5 and PCl3

The reaction of alcohols $\ce{ ROH }$ with $\ce{ PCl5 }$ and $\ce{ PCl3 }$ yields an alkyl halide $\ce{RCl}.$ With $\ce{ PCl5 }$, the reaction is quite simple leading to the formation of $\ce{ RCl }$ ...
14
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1answer
1k views

Is it correct to say that ethenol is an alcohol?

IUPAC Gold Book defines alcohols as: Compounds in which a hydroxy group, $\ce{–OH}$, is attached to a saturated carbon atom $\ce{R3COH}$. However, Wikipedia says that: Vinyl alcohol, also ...
14
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1answer
728 views

Can we synthesize alcohols by the photolysis of hydrogen peroxide?

As I was going through my revision of organic chemistry, I came across free radical substitution of alkanes with halogens. In a similar process where we use hydrogen peroxide, instead of chlorine, so ...
13
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4answers
13k views

Why do hydroxyl groups only produce a singlet in proton NMR?

Take, for example, methanol ($\ce{CH3OH}$). The hydroxyl proton ($\ce{-O$\color{red}{\ce{H}}$}$) is three bonds away from three more protons ($\ce{-C$\color{blue}{\ce{H}}$_3}$), which aren't ...
13
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4answers
6k views

Why can't alcohols form hydrogen-bonded dimers like carboxylic acids?

Carboxylic acids such as acetic acid are capable of forming dimers: I'm wondering why alcohols like ethanol don't generally form dimers. In the diagram below, the oxygen atom on the left ethanol ...
13
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1answer
6k views

Synthetic route for the conversion of ethanol to but-1-yne

How do I convert $\ce{CH3CH2OH}$ (ethanol) to $\ce{CH3CH2C#CH}$ (but-1-yne) ? I'm not too good with reaction mechanisms and conversions are beyond me. My Attempt: I've searched through a couple of ...
12
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3answers
27k views

Migratory aptitude in pinacol-pinacolone rearrangement

I am confused about the migratory aptitude of various groups, as there are many different orders for the same given in different places, especially about -Ph and -H. I would like to know if someone ...
12
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2answers
721 views

Would it be possible to create a (non-toxic) alcoholic drink that, when zapped with laser, changes color?

Would it be possible to create a (non-toxic) alcoholic drink that, when zapped with a 0.5mW laser pointer, changes color? This would be mainly for the visual effects (bartender show) so it should not ...
12
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2answers
34k views

Reactions of alcohol with sulfuric acid

I knew two chemical reactions of alcohol with sulfuric acid $\ce{CH3CH2OH + H2SO4 -> CH2CH2}$ Here product is having a double bond (ethene) and this reaction happens at 443 K temperature. $\ce{...
12
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2answers
1k views

How do I predict the solubility of a compound in a mixture of water and an organic co-solvent?

I'm trying to predict the solubility of long alcohols (e.g. 1-octanol, 1-decanol or 1-dodecanol) in a mixture of water and an organic co-solvent such as DMSO, acetonitrile or ethyl acetate. For ...
12
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1answer
903 views

What are the practical differences between the various DMSO oxidations (Swern, etc.)?

Recently, I was reading a paper about a total synthesis of (+)-rubriflordilactone A (the article is open access: Angew. Chem. Int. Ed. 2015, 54 (43), 12618–12621). In two different steps where an ...
11
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4answers
41k views

How do you create primary amines from alcohols?

By a primary amine I mean a compound where the hydroxyl group of the corresponding alcohol is replaced with an amine group.
11
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1answer
540 views

Why do Grignard reagents add to propargyl alcohols?

In Phil Baran's lectures on heterocyclic chemistry at Scripps, one of the lecture problems is concerned with this synthesis of Vioxx: The first step supposedly involves an anti addition of the aryl ...
11
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1answer
238 views

Which electronic effects are responsible for the reduction of nucleophilicity of a hydroxy group orthogonal to an ester?

I am facing a similar synthetic problem as Boekman Jr. et al noted in their synthesis of Tetronolide.[1] I will quote their’s rather than disclosing my actual synthetic problem, but note that the key ...
11
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1answer
12k views

Reaction of secondary alcohol with ammoniacal silver nitrate (Tollens' reagent)

What are the products of the reaction of 2-butanol with silver nitrate? For the moment, I am a bit stumped as I only have $\ce{AgNO3}$ as an oxidizing agent to form a carboxylic acid from an aldehyde....
11
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1answer
2k views

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 ...
10
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3answers
254 views

Have “molecular clusters” for azeotropes been identified?

A different question about azeotropes got me thinking about this point again. Azeotropes have a very specific composition so it seems that the azeotrope ought to have some sort of physical structure. ...
10
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2answers
1k views

Most stable conformational isomer of 3-methoxycyclohexan-1-ol

Among the following, the most stable isomer is? I am aware of the fact that equatorial substituents are more stable than axial substituents but couldn't proceed to apply it here. However the ...
10
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2answers
21k 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 ...
10
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2answers
2k views

Why is SN2 favored greatly over SN2' in this reaction?

Secondary allylic halides can be produced in high yield with the following Mitsunobu-type reaction:[1] The yield being $94~\%$. The last step in the mechanism is: Why is the $\mathrm{S_N2}$ reaction ...
10
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3answers
7k 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 ...
10
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1answer
1k views

Identification of types of alcohols

An unknown compound was found to react with sodium hydride with the evolution of hydrogen. The compound could not be acetylated under the normal conditions for acetylation. The compound resisted ...
9
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3answers
4k views

Is sodium borohydride really a better base than an alcohol?

I have learnt that sodium borohydride can reduce aldehydes, ketones and acyl chlorides into alcohols. However, it fails to react with esters or acid anhydrides. On the other hand, alcohols — ...
9
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1answer
2k views

Is methanol really more acidic than water?

The question Why is methanol more acidic than water? deals with the reasoning of why methanol is more acidic than water. However, as mentioned in the comments of that question, the acidity constant of ...
9
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1answer
2k views

How could alcohol be made into a powder?

In the news recently is 'Palcohol', powdered alcohol, that you add to water or existing liquids to make it alcohol. Presumably this would dissolve and break apart into alcohol and {some other compound}...
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2answers
10k views

What is the reason that tertiary alcohol pKa is higher than primary alcohol pKa?

A tertiary alcohol has a $\mathrm{p}K_\mathrm{a}$ of 18 while a primary alcohol has a $\mathrm{p}K_\mathrm{a}$ of 16. Shouldn't the tertiary alcohol be more acidic since its conjugate base is more ...
9
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1answer
2k views

Why is an alcohol proton so shielded?

Considering how electronegative oxygen is, why is the chemical shift of alcohol protons (1H-NMR) not so high? The chemical shifts of the protons on 3-propanol are about 1.20 for the carbon-1 hydrogens,...
8
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2answers
13k views

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

Why is thionyl chloride ($\ce{SOCl2}$) preferred for preparing alkyl chlorides from alcohols, as opposed to say $\ce{PCl5}$ or $\ce{PCl3}$ ?
8
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2answers
11k views

Polarity of alcohols and their miscibility in water

I am an AP Chemistry student and there is a small detail concerning polarity of molecules that I am confused about. My review book (Princeton review) says that ethanol has stronger intermolecular ...
8
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1answer
250 views

How to explain this acid-catalysed acetal rearrangement mechanistically?

I have spotted a protecting acetal group and thought this would undergo hydrolysis … My working is such: But I cannot get to the desired isomer. Could someone please help? (Diagrams would be very ...
8
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3answers
366 views

Can aldehydes be reduced to alcohols efficiently using LiAlH4 (excluding cost effectiveness)?

In my textbook (NCERT 12th class Chemistry, Part 2, India), $\ce{H2}$ with $\ce{Pd}$ catalyst is the only method mentioned.
8
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2answers
465 views

Non-halogen intermediate between alkane and alcohol under basic conditions?

Using organic chemistry I have failed to find a method that doesn't involve halogens (gasseous especially). Please ignore the enzyme mono-oxygenase, which adds $\ce{O2}$ directly to alkanes to form ...
8
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2answers
619 views

Producing ketones from secondary alcohols using hydrogen peroxide

Usually, to produce ketones from secondary alcohols (e.g. propanone from 2-propanol), people use a solution of potassium or sodium dichromate with a small amount of sulfuric acid. Can other oxidizers ...
8
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1answer
407 views

Can thionyl bromide produce alkyl bromides?

Thionyl chloride ($\ce{SOCl2}$) is used with alcohols to produce alkyl chlorides. Similarly, can thionyl bromide ($\ce{SOBr2}$) be used with alcohols to produce alkyl bromides?
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3answers
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Is there a way to turn alcohol into a solid gel?

I'm wondering if there is a way to turn alcohol or another bacteria killing substance into a solid gel form, sort of like the gel you can use to clean a keyboard. Source: Aliexpress.com Computer ...
8
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1answer
681 views

Treatment of allylic alcohol with thionyl chloride: why is the product rearranged?

I have read that $\mathrm{S_Ni}$ reactions involving the attack of $\ce{SOCl2}$ on alcohols proceed without the formation of discrete carbocations, and hence there is no rearrangement involved. But ...
8
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1answer
18k views

Comparison of rate of dehydration of primary, secondary & tertiary alcohols on cyclohexane

Rate of dehydration when given compounds are treated with conc. $\ce{H2SO4}$ is According to me the answer should be $R > Q > S > P$ but my textbook solution gives the answer as R > Q > P > ...
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0answers
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Why can't I dry/concentrate ethanol using calcium chloride … or can I?

My (very unreliable) school textbook tells me: Lower alcohols form a solid derivative with certain metal salts. and, It is for this reason that ethanol cannot be dried/concentrated using ...
7
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2answers
705 views

Are there ethanol and methanol analogues with more than one hydroxyl group?

Ethanol and methanol are ethane and methane derivatives, respectively, with one hydrogen replaced by an hydroxyl group. Are there molecules based on either where more than one hydrogen atom has been ...
7
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2answers
904 views

Why does formaldehyde exist primarily as the gem-diol in aqueous solution?

From Wikipedia, Methanediol is the product of the hydration of formaldehyde $\ce{H2C=O}$, and predominates in water solution: the equilibrium constant being about $10^3$ and in a 5% by weight ...
7
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2answers
9k views

Does ethanol react with potassium to form potassium ethanolate and hydrogen gas?

I'm finding information in Google with the keyword (C2H5OH + K) to find the reaction between $\ce{C2H5OH}$ and $\ce{K}$ and found very little information about it. Just 2-3 related results with ...
7
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2answers
499 views

Retrosynthesis of a lactone

We have been asked to do a retrosynthesis of (6⁠S)-6-[(2⁠S)-2-hydroxy-4-phenylbutyl]oxan-2-one J from 3-phenylpropan-1-ol K: My first instinct would be to do a functional group interconversion of the ...
7
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2answers
23k views

Why is ethanol written as C2H5OH not C2H6O?

This is balanced equation of fermentation of glucose: $$\ce{C6H12O6(aq) -> 2C2H5OH(aq) + 2CO2(g)}$$ I know that the result of glucose fermentation is ethanol ($\ce{C2H6O}$). What represented in ...
7
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1answer
480 views

Does “soluble in alcohol” imply ethanol?

Sources like Wikipedia and SolubilityOfThings say that copper (II) acetate is soluble in alcohol. Does that mean any alcohol, or does "alcohol" in this context mean ethanol?