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 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 ...
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1answer
2k views

Conversion of an alcohol to a methyl group

I'm only interested in the first conversion: D to E. I've been thinking about this for a little bit. My first thought was to use $\ce{TsCl}$ to make a good leaving group then a $\ce{Me}$ nucleophile. ...
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376 views

Number of intermediates and transition states in hydration of given alkene

What is the number of transition states and intermediates formed in the following reaction? My thought: First the alkene extracts $\ce {H^+}$ from the acid to form a carbocation. This step ...
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561 views

Can oxidation of ethanol by copper(II) oxide yield copper(I) oxide as one of the products?

We know that ethanol is oxidised by copper(II) oxide to an aldehyde. Copper is reduced from $\ce{Cu^2+}$ to $\ce{Cu}$. Can this reaction, with some specific condition, yield $\ce{Cu2O}$ instead? That ...
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44 views

Ethyl acetate produces red colour on ceric ammonium nitrate test

When I did CAN test on ethyl acetate red colour was seen. I thought water may get added with Ethyl acetate to produce this compound which in turn gave red coloration but carbon should not make three ...
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159 views

Major product of isomerization reaction

I am trying to come up with a logical mechanism for the following transformation, where 2-methylenecyclobutan-1-ol is converted to cyclopentanone under acidic conditions: What I have tried to do was ...
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179 views

How to make a placebo drink taste convincing?

I'm trying to make a placebo alcoholic drink - something strong (cognac, whiskey or vodka). Is it possible to make a drink containing absolutely no alcohol taste like it's got 30 or 40% alcohol? What ...
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157 views

How can I purify ethanol from formic / boric / salicylic acid?

I need some ethanol pure and strong enough for technical purposes (fuel, solvent, cleaning agent, dissolving rosin for soldering flux, etc.). Food quality is not required though, denaturated one is ...
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91 views

Catering grade electrolysis of alcohol

Would the electrolysis of alcohol, specifically spirits, result in a potable end product? I'm looking for some novel cocktail ingredients.
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142 views

Addition of NaBH4 and LiAlH4

NaBH4 and LiAlH4 will be a source for the hydride ion and reaction will begin with addition of hydride by displacing the carbonyl group. But I am not sure will it attack both the carbonyl or only one....
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1answer
284 views

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).
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179 views

PF3 as a source of fluoride for substitution in alcohols

It is known that $\ce{PX3 (X= Cl, Br, I)}$ and $\ce{PX5 (X= Cl, Br)}$ are used to make halogen derivatives of hydrocarbons from alcohols. My question is why there's no information about using $\ce{PF3}...
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749 views

Is 70% ethanol hygroscopic?

I'm currently doing some DNA extractions and I realized that in some protocols, they are saying that ethanol is hygroscopic. In this source, they are saying: 85% ethanol made with nuclease free ...
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157 views

Acid-catalyzed epoxide opening

For the acid catalyzed opening of epoxides, the epoxide is first protonated to form the oxonium ion. I read in some textbooks that the $\ce{H2O}$ molecule, which acts as a nucleophile attacks in a $\...
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Will oxalic acid react with ethanol?

Will oxalic acid, in a saturated solution in ethanol, be able to undergo an esterification reaction with the ethanol? This is assuming no acidifying agents (or anything else, for that matter) are ...
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87 views

What determines whether iodination or reduction will occur?

Alkyl Iodides are formed by reaction of alcohols with iodine and red phosphorus. I already am well aware that this forms $\ce{PI3}$ in situ, which acts similarly to $\ce{PBr3}$ and allows alkyl ...
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29 views

Rate determining step in oxidation of alcohols using chromium-related compounds

I wanted to ask a question about the kinetics of an oxidation reaction using chromium reagents. I was given a lecture today on the mechanism of alcohol oxidations using Chromate (VI) reagents: My ...
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31 views

Is the reaction of anhydrous aluminium(III) chloride and anhydrous ethanol reversible?

I'm planning an experiment that I'll do in silico in the near future, and one of the steps involves the extraction of the $\ce{AlCl3 · C2H5OH}$ adduct without any water in it. Can the ethanol be ...
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27 views

Diketone intramolecular reaction question

I realize that one of the methyl groups on either carbonyl compound will become deprotonated and then it will attack the other carbonyl to form a pentane ring. However, with the methyl group in the ...
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39 views

Hemiacetal formation mechanism

The question is asking which reagents can be used to carry out this reaction. I get the L (PCC) is used to turn the primary alcohol into an aldehyde. However, I believe that is not the only reagent ...
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44 views

Does 2,2-dimethylpropan-1-ol give a positive Lucas test?

I learnt that the Lucas test involves the formation of a carbocation and it gives a positive test based on the stability of the carbocation formed, and hence primary alcohols do not show turbidity (...
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34 views

Comparing the emission spectrum of ethanol and mixture of alcohols

Sorry if this question has a simple answer, but I've been unable to find it elsewhere. Using a diffraction grating, burning ethanol (99.9%) will produce a rainbow of colours. However, when burning ...
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56 views

Oxidation of diols to dialdehydes

How could 1,4-butanediol be converted to 1,4-butandial (succinic aldehyde)? I thought of simple oxidation with CuO but apparently it yields gamma-butyryllactone according to erowid (https://erowid.org/...
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Is there a simpler way to detect alcohol in a blood sample using IR spectroscopy?

I have seen all sorts of ways to detect alcohol using NIRS (Near InfraRed Spectrscopy) or FTIR, but they are all quite complicated in that they are using and analyzing a very wide spectrum. In ...
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23 views

Using Wilkinson's Catalyst to reduce esters?

I was solving some questions on alcohols when I came upon a question in which it was asked that whether esters can be reduced using hydrogen in the prescence of wilkinson's catalyst. Now I know that ...
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67 views

Potassium ethoxide

Is it possible to make potassium ethoxide by mixing $\ce{KOH}$ and $\ce{EtOH}$ in the presence of a dehydrating agent like $\ce{MgSO4}$ or $\ce{CaO}$ or $\ce{K2CO3}$? The easy way is adding metallic ...
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57 views

How does alcohol infusion (maceration) work chemically?

To make liqueurs (e.g. lemon liqueur) you take some fruit and/or plant and let them macerate in pure alcohol to make the alcohol have the fragrance and color of the original ingredient. How does it ...
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87 views

Can ethylene glycol give victor mayer test?

I think there should be no problem for it to give red coloration in victor mayer test as a standard primary alcohol but a problem I encountered showed it otherwise. Therefore, I would like to have a ...
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57 views

Approaches to cap/modify the terminal 3' OH of DNA polymer

I am looking for a procedure that would cap/protect the 3' hydroxyl of DNA molecules with high efficiency. I have tried to perform a similar step enzymatically using dideoxynucelotide triphosphates ...
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126 views

Bond angles in a oxonium cation

What are the bond angles in protonated alcohol? The bonds in the carbon chain are presumably unaffected by the $\ce{-O^{+}H2}$ group and so in their usual tetrahedral arrangement; what are the angles $...
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634 views

What is the function of ZnCl2 in lucas test?

One mechanism I found on the internet (even on chemistry stackexchange) for the lucas test is: Here I don't see ZnCl2 participating in any of the steps. So what does it actually do? Another ...
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373 views

Solubility of Calcium Oxalate in Aqueous Alcohol?

In searching through the literature for the solubility of calcium oxalate, I came across this post https://www.researchgate.net/post/Are_there_any_organic_inorganic_solvents_for_dissolving_Ca-oxalate ...
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34 views

Distillery Transfer Hoses

I was hoping an actual person could offer me some advice. I work in a craft distillery and I'm getting a lot of mixed information on how compatible PVC is with high-proof alcohol. It definitely seems ...
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98 views

Calcium based Corrosion-Inhibitors used in Ethanol fuel, and their effect on the organic-solvent abilities of that alcohol?

Ethanol is a good organic solvent, often the preferred non-toxic choice for the processing of plant extracts. One of the cheapest sources of Ethanol is the kind used in fireplaces and racing fuel, but ...
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253 views

Parts Per Million

I am trying to calculate how many milliliters of a solution I cannot exceed to create $\pu{200ppm}$ in the air of isopropyl alcohol. The $\pu{26ml}$ bottle of solution is 70% isopropyl alcohol. Using ...
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5k views

How to make a primary alcohol from an alkane?

Alcohols can be made from alkyl halides, which can be made from alkanes. However $3° > 2° > 1° > 0°$ for alkyl halides synthesis from alkanes. What approach could make an alkane with primary ...
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101 views

How to write a reasonable mechanism for the reaction of alcohols to synthase ketone?

In the section of reactions of alcohols in my textbook, there are no mechanisms or explanation for this reaction: I am interested in Jones Oxidation particularly. I researched a little bit on ...
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116 views

Are there common diluents for oils that will not cause an emulsion when added to water

If I combine a viscous oil into solution in a carrier in a ratio of between say 1:10 or 1:100 to make it low viscosity but not separate into layers. I then place a few drops onto a larger quantity of ...
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537 views

High quality phase diagram for ethanol

I know the more general question has been asked here: Open Database of Phase Diagrams? And this has a link to slightly more specific question with more answers: Phase diagram for first 10 elements ...
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What exactly is an 'activated' alcohol? Benzylic vs. Allylic vs. Aliphatic

I'm currently writing a report about the oxidations of various alcohols using different catalytic systems. In all papers it is stated that benzylic and allylic alcohols are "activated", while ...
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27 views

Nucleophilic Substitution Reaction of Alcohol

What is the final product? According to me, it's option (3). But given answer in the booklet is (2). Given primary alcohol undergoes SN2 reaction to produce isopentyl bromide and the latter again ...
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18 views

How to confirm experimentally that a hemi-acetal compound has formed?

I have read that under mildly acidic or alkaline conditions alcohols can attack aldehydes/ketones to produce hemi-acetals. But the reaction is reversible, so the reactants and the hemia-cetal are in ...
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Alcohol Nonmeclature - Organic Chemistry

I'm new to organic chemistry and having some trouble naming alcohols. I came across this molecule, I believe it's name is 3-ethyl 2-pentanol, but my online checker system is saying that I am wrong. Am ...
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Why does energy need to be “compensated” in order for solvation to occur?

I am currently learning about the physical properties of alcohols. I understand that the main intermolecular forces between alcohols and water are hydrogen bonds. When these two are mixed, the ...
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1answer
140 views

Why primary alcohol follows 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 ...
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299 views

Why is Lithium Chloride (LiCl) soluble in alcohols?

According do J.D. Lee's Concise Inorganic Chemistry, LiCl is soluble in alcohols because it has some covalent nature, althought it is mainly polar. Why would LiCl have covalent character? Why doesn't ...
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229 views

Victor Mayer test for 2° alcohol

In the last step in Victor Mayer test for 2° alcohol, why do we need to add an alkali like NaOH? Isn't pseudo nitrolic acid that is formed already blue in colour? What would be the reaction of alkali ...
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42 views

Comparing acidity in 3,4-dihydroxyfuran-2(5H)-one and 2,3-dihydroxycyclopent-2-en-1-one

I have two compounds with two hydrogens namely (a),(b),(c) and (d). I have to compare the acidity of the following hydrogens. My approach: I removed the hydrogen atoms one by one and compared the ...
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92 views

Ethyl Acetate and other Solvents in a mixture: miscibility and stability

I was wondering about a heterogeneous solvent mixture containing multiple alcohols such as IPA, Ethanol, methanol etc. Would EtOAc (Ethyl Acetate) play nice in these mixtures at low volumes such as 1 ...
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55 views

Should I use MCPBA here?

I came across a question that asked for a method to convert propene to glycerol. I used the method in the pic, but I'm worried about two steps- Step-2, This reaction is just made up by myself! I'm ...