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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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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96 views

Why isn't PBr3 used to halogenate tertiary alcohols?

I've been looking into activation of alcohols for nucleophilic substitution, and I've come across a series of reactions that differentiate between primary, secondary and tertiary alcohols. I've seen ...
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485 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 involves ...
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604 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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34 views

Reducing olefinic bond in conjugation with C=O bond using LiAlH4

I'm studying the synthesis of alcohols. One of the methods given is "Reduction with metallic hydrides like $\text{LiAlH}_4$". Under this title the following reaction has been listed [1, p....
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1answer
76 views

Why does the C−H bond dissociation energy vary in a homologous series of primary alcohols?

Specifically, for the primary carbon atom in the alcohol. Here is bond dissociation energy (BDE) data from chapter three of Luo's Comprehensive handbook of chemical bond energies [1] (boldface refers ...
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108 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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213 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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1answer
406 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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207 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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162 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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95 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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1,5-Pentanediol MS

I'm having troubles assigning the signals m/z = 41 and 56 of the compound 1,5 pentanediol. I tried the basic fragmentations (McLafferty, loss of OH radical, etc.) but I can't figure the structure of ...
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143 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 $20^{\circ}C$). ...
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176 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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237 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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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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177 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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3k views

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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92 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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1answer
313 views

Reactivity of different alcohols with NaNH2 and CH3I

Identify the final product (B) in the following reaction: I'm not sure how $\ce{NaNH2}$ and $\ce{CH3I}$ will react with the different types of alcohol present here. According to my solution,ether was ...
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35 views

While treating 4-aminophenol with acetic anhydride why does the reaction stop at Paracetamol and does not undergo esterification with acetic acid?

This needs a little background so I will be showing you a question from one of my Organic Chemistry problem books:- Now, the book shows the answer as Option (c) which is Paracetamol. I tried to work ...
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47 views

Why does Ethylene Glycol have higher boiling point than Propylene Glycol?

Looking at the two alcohols, both have hydrogen bonding and are singly bonded throughout the molecule. However, propylene glycol has a larger electron cloud which to my knowledge would increase its ...
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32 views

Red Compound from Glycine and Glycerol?

I got an unexpected reaction which I'm trying to explain to myself: I mixed 10 parts glycerol with 1 part glycine at ~90C and to my great surprise the mixture turned from transparent to a tint of red. ...
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28 views

What fluid can I store metal filings in so they do not oxidize?

I am working on an art project that will involve storing filings of various metals (e.g., iron, copper, zinc) in a colorless fluid. I want to prevent the metals from oxidizing for several years, so ...
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74 views

Proton NMR of tert-amyl alcohol

I just started learning about proton NMR. According to Molbase, the HNMR data for tert-amyl alcohol (2-methylbutan-1-ol) shows four kinds of protons at 0.9 ppm, 1.24 ppm, 1.44, and 3.65 ppm. However, ...
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49 views

Water solubility comparison of stereoisomers of bicyclo [4.4.0] decane-3,4-diol

I think, (I) must be more soluble in water. It is due to trans configuration and thus, forming more effectively inter-molecular hydrogen bonds with water molecules.
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213 views

Solubility of alcohols in non-polar solvents

The solubility of an alcohol in a non-polar solvent (like hexane) increases with size of the alcohol, as the non-polar chain increases. However, as the chain keeps increasing, will the solubility ...
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73 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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110 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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46 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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51 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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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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91 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 $\ce{CuO}$ but apparently it yields gamma-butyrolactone according to erowid and this ...
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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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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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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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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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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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58 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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144 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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867 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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476 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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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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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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260 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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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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108 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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134 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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558 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 ...