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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132 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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79 views

Why is chlorosulfite a good leaving group?

I came across the following website article[1]: I understand the mechanism and also get the fact that this is nothing but an experimental result but why does the $\ce{ClSOO-}$ group departs ...
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When does reaction of alcohol with alumina give ethers and when an alkene?

This problem given in my book confused me a little bit: when an excess of ethyl alcohol vapour is passed over heated alumina ($250^\circ$C), the main product is? I read that this reaction gives an ...
4
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1answer
479 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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531 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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617 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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92 views

Making a bridge on a cyclic molecule

So, my question is how would I make a bridge as seen on the following molecule (right side)? As for the molecule on the left, I am supposed to make it using that molecule as a base. The only ...
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50 views

Is it possible to distinguish between cyclohexanol and cyclohex-2-en-1-ol with simple chemical test?

Primary, secondary and tertiary alcohols can easily be distinguished by using reagent tests such as: The triiodomethane test for $\ce{R-CH(CH3)OH}$ alcohols. Lucas' reagent to distinguish between ...
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135 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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143 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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1answer
209 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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236 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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220 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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167 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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97 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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1answer
100 views

Determining the mechanism followed when alcohols undergo a reaction with sodium bromide and sulphuric acid

$$\ce{R-OH + NaBr + H2SO4 -> R-Br + NaHSO4 + H2O}$$ Due to sulphuric acid, the $\ce{-OH}$ group will get protonated and convert into $\ce{-H2O+}$ which is a great leaving group in comparison to the ...
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1answer
658 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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22 views

Which one out of a keto group or a hydroxyl group would get protonated first if both are present in a compound (attachment)

In the solution provided by my teacher he protonated the ketone, moved the +ve above by resonance did methyl shift and then did dehydration to form a benzene type system. Is this only because for this ...
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52 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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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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188 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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257 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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181 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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97 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
175 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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1answer
45 views

On the relative ease of E2 dehydration

Concerning alcohol dehydration, I get that it's E1 in secondary and tertiary alcohols, that it's E2 in primary alcohols, and also why E1 reaction is easier for tertiary alcohols as compared to ...
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43 views

Confusion regarding dehydration of 1° alcohols

My lecturer told me that 2° and 3° alcohols prefer to dehydrate through E-1 mechanism. On the other hand, 1° alcohols tend to prefer the E-2 mechanism, which does not involve the formation of a ...
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26 views

Will OTs ever act as a nucleophile and substitute with an alcohol?

If you reacted TsOH with a secondary or tertiary alcohol, will you ever see a racemic mixture of OTs substituted products after the water group leaves? Is OTs just too weak of a nucleophile to ever ...
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305 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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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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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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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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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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410 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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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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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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60 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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54 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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103 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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50 views

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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104 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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60 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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150 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 $...