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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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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466 views

How to tell the difference between octane-1-ol and oct-1-ene?

How to tell the difference between octane-1-ol and oct-1-ene? The things I can do are: check their solubility in water use bromine water use $\ce{KMnO4}$ use sulfuric acid I assumed that checking ...
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1answer
130 views

How long does a wine sauce need to simmer for to reduce the alcohol to less than one percent [closed]

Perhaps you can shed some light on this topic for me. I've recently researched the topic of boiling off alcohol while cooking--specifically how long one needs to simmer alcohol to boil it off. I'd ...
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4answers
163 views

Chlorinating specifically one carbon on a symmetrical alcohol

The final target molecule is 1-chloro-2-amino propane. The amination step would be simple via reductive amination of 1-chloro-iso-propanone. Obtaining 1-chloro-iso-propanone would be from ...
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0answers
213 views

Mechanism for the formation of an alkyl halide from alcohol and phosphorus trihalide [duplicate]

I was reading about synthesis of alkyl halides from $\ce{PX3}$. I want to know the mechanism for this reaction. According to Solomons and Fryhle, no rearrangement takes place in case of $\ce{PBr3}$ , ...
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1answer
3k views

Reaction of ethylene glycol with acidified potassium permangnate

One would expect the reaction of ethylene glycol with acidified potassium permangnate to result in oxidation of ethylene glycol to oxalic acid. But a Q&A guide book tells me it is oxidized to ...
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1answer
347 views

Mechanism for the conversion of an unsaturated alkyl halide to an alcohol

Question: Predict the mechanism for the following reaction: Attempt: I thought it will proceed through SN1 mechanism as $\ce{H_2O}$ is involved (solvolysis). So I proceeded with the formation of a ...
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1answer
1k views

Isopropyl alcohol still leaves evaporation residue after distillation

I just finished distilling two liters of IPA because evaporating 5 ml on a watch glass revealed it to contain quite a bit of dissolved impurities. However, it still leaves some residue, even though I ...
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1answer
555 views

Do I really need to wear protective clothing while using isopropyl alcohol? [closed]

I recently purchased a 500ml bottle of 99% isopropyl alcohol (aka isopropanol aka rubbing alcohol) for everyday use at home. The label for the bottle worryingly states: Wear protective gloves/...
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3answers
10k views

How to test for methanol?

I wanted to make some ethanol from baker's yeast and I used sucrose. I've made it and put it in a glass jar. I left it on a warm place (near the radiator) until the yeast died and after they died I ...
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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 ...
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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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3answers
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Can 99% isopropyl alcohol be stored in a clear container?

I'm planning to get hold of some 99% isopropyl alcohol (aka rubbing alcohol) for the purpose of cleaning electronics, and am going to transfer it from the plastic bottle it comes in to a smaller, ...
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2answers
806 views

IUPAC naming of quinol and hydroquinone

This is benzene-1,4-diol. Its common name is quinol and hydroquinone. How is hydroquinone an accepted name since the functional group here is an alcohol and not a ketone? Is this the only such case or ...
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1answer
317 views

Are allylic three degree alcohols oxidized by the Jones' reagent via a classical carbocation intermediate?

I know the mechanism for Jones' oxidation is (picture from Organic Chemistry by Clayden): and it proceeds through a chromate ester. And in general we understand that the Jones' reagent $\ce{H2CrO4}$ ...
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1answer
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Ethanol in gasoline — will it evaporate?

If gasoline with 10% ethanol is stored for a few weeks, will the ethanol evaporate? I have read that to check for ethanol in gas is to add a little water to a container; mark the level and add gas. ...
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1answer
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Why doesn't the bromide anion attack during electrophilic addition of bromine in methanol solvent?

It is known that addition of bromine (in methanol) to ethene will yield 1-bromo-2-methoxyethane. The reaction proceeds with the formation of a bromonium intermediate in the first step. In the second ...
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1answer
86 views

Is an allene or a conjugated diene formed?

If we dehydrate the following molecule, which hydrogen ($\ce{H1}$ or $\ce{H2}$) gets removed? The conclusion that I have drawn from the molecule: The carbon to which $\ce{H1}$ is attached is $\ce{sp2}...
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2answers
1k views

Can ethanol be both a Lewis base and a Lewis acid?

I'm asked to determine if ethanol is a Lewis acid, Lewis base, or both. Since $\ce{O}$ has two lone pairs of electrons I would think that it could act as a base, since they could easily be donated. ...
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0answers
137 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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0answers
1k views

Does ethanol conduct electricity? [duplicate]

I am trying to find out about methylated spirts/denatured alcohol. As far as I can fine, methylated spirits is roughly 95% ethanol. Will it conduct electricity? I have done some research, but I have ...
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1answer
1k views

Polarity and acid strength in alcohols

I'm totally confused about the relationship between the polarity and acid strength of a given compoud. Take the case of alcohols itself, it's said that primary alcohols have greater acid strength ...
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0answers
840 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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1answer
817 views

How to choose alcohol solvent for organic extraction?

Assuming I have an organic substance that is known to be "soluble in alcohol" (e.g. capsaicin) I want to extract, which alcohol should/can I use? I know that both ethanol and methanol are commonly ...
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1answer
88 views

Name of corresponding anion of a hemiacetal

If a hemiacetal is deprotonated at its hydroxyl group, what is the correct name for the resulting anion (or salt)? I could not find anything, and assume that these compounds are probably not stable (...
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1answer
3k views

For what reasons, is isopropyl alcohol widely used as a cleaning solvent?

I have worked in electronics and aeronautics industry 30 years ago, and I have always wondered, what were the specific properties of isopropyl alcohol, which make it used instead of other alcohols ...
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1answer
1k views

How is using Jones reagent different than Potassium dichromate in Sulfuric acid for the oxidation of alcohols?

I was taught at an institution I study in that using $\ce{K2Cr2O7}$ in the presence of $\operatorname{dil}.\ce{H2SO4}$ will oxidise $1^{\circ}$ alcohols to aldehydes, and $2^{\circ}$ alcohols to ...
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1answer
339 views

Are gem-diols on alkenes stable?

Geminal diols are unstable, except for a few exceptions like chloral hydrate. I wish to ask if a gem-diol alkene is also stable. Their structure: suggests to me that the intramolecular hydrogen bond ...
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1answer
584 views

Reaction of vicinal diol in presence of benzaldehyde

Could someone please help me figure out the products of the following reaction? Here are few possibilities I've come up with: The attacking reagent could the given vicinal diol, with its ...
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2answers
490 views

Is HDPE affected by long term exposure to methanol?

For at least several years I'be been storing various chloride solutions with methanol as a solute in Nalgene containers, which I believe are made from high density polyethylene (HDP). But recently ...
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2answers
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Mechanism of Oxymercuration-Demercuration reaction

I am trying to write a mechanism for OMDM reaction. I could write the mechanism for oxymercuration part of reaction but I couldn't write the mechanism for remaining part (demercuration) of the ...
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0answers
453 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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1answer
384 views

Hydroboration on Limonene

I saw that the hydroboration of Limonene (1-Methyl-4-(1-methylethenyl)-cyclohexene) does only happen on the methylethenyl group. Up to now, I wasn't able however to find out why. Generally speaking, a ...
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2answers
530 views

Can hydroxides ionize alcohols?

For example, can $\ce{NaOH}$ ionize ethanol into ethoxide? My textbook (Organic Chemistry, 6th edition, by M. Loudon and J. Parise, Roberts & Company 2016) suggests yes — it uses it in its ...
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0answers
463 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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255 views

Why droplets of water and ethyl alcohol solution freeze weirdly? [closed]

I'm doing a project where I freeze water drops and solutions with water and ethyl alcohol. It's a phenomena where drops create a conical shape at the end of their freezing. But with ethyl drops, with ...
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1answer
2k 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 ...
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2answers
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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
710 views

How do I arrive at the α-trimethylsilyloxy ketone from an unmodified ketone using TMSCl, triethylamine and mCPBA?

I'm confused about what is going on here. I gather that step 1 is typically supposed to protect an OH group, but there isn't any in the starting material.
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2answers
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O-H infrared band dependence of alcohol concentration in water

With regard to IR spectroscopy, how would the O-H band change as an alcohol solution was diluted with water? I am referring to any alcohol, but for the sake of example we can use ethanol. I think ...
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0answers
223 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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1answer
323 views

Why don't Gringard Reagents react with carbonyls at the alpha position? [duplicate]

According to many texts, the reason why Gringard reagents cannot be used with alcohols is because the Gringard reagent is a strong base, which would deprotonate the alcohol. ($p\pu{K}_b$ of Gringard $\...
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2answers
601 views

Unknown alcohol sample. Chromic acid negative but iodoform positive?

I have a unknown sample of an alcohol (ceric nitrate positive) but when I did chromic acid test it was negative since it never turned into blue/green and against all odds iodoform was positive... ...
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36 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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1answer
2k views

What happens when aluminum reacts with tert butyl alcohol? [closed]

I wanted to know that what happens when aluminum reacts with tert butyl alcohol..?
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1answer
645 views

Mechanism for bromoetherification of olefinic alcohol

Propose a mechanism for the following reaction showing the relevant stereochemistry of intermediates and the final product. I am confused as to what is going on here. I guess there's some sort of ...
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1answer
447 views

Why can unsymmetrical tert-butyl ethers be prepared by dehydration of the constituent alcohols?

Practice problem 11.11 what stops R-O-R from forming at the same rate as the desired product?
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1answer
874 views

Synthesis of methylenecyclohexane from cyclohexylmethanol

I want to form methylenecyclohexane from cyclohexylmethanol I'm thinking about an $\mathrm{E1cB}$ mechanism since the β-hydrogens will be quite acidic (similar electronegativity to fluorine). ...
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0answers
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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1answer
749 views

calculate the number of shots of Captain Morgan’s rum

I am facing a challenge, and this is my first question in this stack exchange. I have worked out the following problem but the answer I got (number of shots) is ridiculous. Could any of the chemist ...

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