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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Oxidizing 2-Methylpropan-2-ol using potassium dichromate. Why is heating required?

In Chemistry class, we had to combine $\ce{K2Cr2O7}$ with 2-Methylpropan-2-ol and heat it for the oxidation to occur. But why do we have to heat the mixture when, for example, butanol, can be ...
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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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1answer
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How to name molecules with a hydroxyl group in a side chain?

TL;DR: Are there clear nomenclature rules for naming the below molecule? Today in school we learned about the nomenclature of alcoholes. Unfortunately, it was not mentioned what to do with hydroxyl ...
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Will glycerol and citric acid react? If yes, under what conditions?

I would like to know whether the reaction will take place if glycerol and citric acid are merged? In particular, what will happen if both substances are heated up to high temperature (+100°C)?
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How to convert isopropanol to acetone and hydrogen

From Wikipedia: Isopropyl alcohol can be oxidized to acetone, which is the corresponding ketone. This can be achieved using oxidizing agents such as chromic acid, or by dehydrogenation of ...
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219 views

organic chemistry of alkyl halides and alcohols

What happens if a primary alcohol that also bears a halide substituent on the alcoholic carbon (the carbon to which the hydroxyl group is attached) when it is reacted with copper at 300 °C ? I ...
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1answer
2k views

how to define proper ppm concentrations for water solvent vs alcohol solvents?

1 ppm is 1 mg / kg Water density: 999.97 kg/m³ methanol density: 791.80 kg/m³ solution 1 with water as solvent: at 1 $\ce{\mu}$g / mL is considered 1 ppm solution 2 with methanol as solvent: at 1 $\...
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Solubility and Evaporation - Would the concentration still be 1 ppm?

A certain salt has a solubility of 1 mg/1 L. I have 1 mg of this certain salt dissolving in 1 L of water, I have a concentration of 1 ppm. 1st Question: If the solution is left open to evaporation, ...
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1answer
108 views

Reaction between 1-methylcyclopentanol and potassium permanganate

In my basic organic chemistry class, I learned that only primary and secondary alcohols undergo oxidation (using $\ce{KMnO4}$). However, what is the outcome of reacting tertiary alcohol (1-...
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107 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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976 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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Do secondary alcohols prefer to undergo SN1 or SN2 reactions when reacting with a strong acid?

For example, let us say we have 2.2-dimethycyclohexanol reacting with $\ce{HBr}$. We know that the oxygen gets protonated and then leaves as water, but the question does it leave on its own or does a ...
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Pinacol pinacolone rearrangement

I was reading the topic alcohol in that I saw a reaction Pinacol pinacolone rearrangement . But I am not able to find the sterochemistry of the reaction . Can anyone please tell me the ...
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Does glass adsorb methanol to an exceptional extent?

Does (borosilicate) glass adsorb methanol to an exceptional extent? We are doing vapor density measurements of organic solvents using a microbalance and a sealed glass sphere. Other polar molecules ...
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1answer
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Extent of dehydration by conc sulphuric acid

I know that conc $\ce{H2SO4}$ is dehydrating agent. And the most easiest mechanism example would be this, But ,I want to know how to find theextent of dehydration of it. I came across this question ...
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1answer
201 views

Are all carbohydrates a subset of alcohols?

According to the definition, an alcohol is any organic compound in which the hydroxyl functional group (-OH) is bound to a saturated carbon atom. Monosaccharides such as glucose contain several ...
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Why is sodium methanethiolate still a better nucleophile than sodium methoxide when the solvent is ethanol

I'm looking at a problem where sodium methanethiolate and sodium methoxide, both in equal amounts, are being reacted with $\ce{CH3I}$ and the solvent is ethanol. I understand that sodium ...
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1answer
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Which mechanism should a reaction between the cyclopentylmethanol and the HBr should follow?

I just thought that the reaction should follow $\mathrm{S_{N}2}$ mechanism this is because the alkyl halide is primary but the book says that the reaction will follow $\mathrm{S_{N}1}$ mechanism ...
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1answer
91 views

What is the name of this organic compound?

The organic compound in question is shown above. This is how I tried to name it: Start from the left hanging $\ce{H_3C}$. $\ce{OH}$ gets the number 2 and $\ce{NH_2}$ gets 6. The lowest numbers ...
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603 views

Mixing alcohol with aluminum sulphate

I am trying to make a mixture of the following ingredients: distilled water, alcohol, aluminum sulphate and glycerin. The problem is that when I add alcohol to the water and aluminum sulphate mixture ...
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1answer
278 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
986 views

Why do esters have to be distilled during purification?

I am currently designing a lab experiment for a school project in which I am to determine the effect of catalyst concentration ($\ce{H2SO4}$) on the rate of reaction between methanoic (formic) acid ...
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Correction formula for alcoholmeter

I need to find the formula, if there is one, which would calculate the correction of alcoholmeter. Basically convert observed %ABV (Alcohol by volume) to actual %ABV using the sample's temperature. ...
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What happens when prop-2-en-1-ol reacts with concentrated hydrogen bromide

What happens when prop-2-en-1-ol (allyl alcohol) reacts with concentrated hydrogen bromide? My Idea: I thought that in the first step protonation of the hydroxyl group will take place followed by ...
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Is a polycarbonate beer mug appropriate for serving alcohol?

Are polycarbonate & acrylic beer mug, whiskey glasses safe for serving alcohol? I mean does it leach or dissolve? What are the harmful effects in long run if any?
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706 views

Enthalpy of formation and bond energies of CH2(OH)2?

I was wondering if I could have the bond energy and enthalpy of formation in kJ/mol for $\ce{CH2(OH)2}$? I honestly searched the Internet and my textbook and I couldn't find it. I'm sure I could ...
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185 views

Do sugar alcohols have the potential to get a person drunk?

From what I understand is ingesting high amounts of sugar alcohols can lead to various effects such as abdominal pain and diarrhea, my question is, is there a certain amount of sugar alcohol if ...
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Grignard alkoxide intermediate as starting material for ether or ester synthesis

I'm having a Grignard reaction between a ketone or aldehyde with RMgX in mind. The average workup uses water to hydrolize the intermediate alkoxide. But could this intermediate be used without ...
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1answer
89 views

Can you lower the alcohol concentration of a drink using vegetable oils?

The log POW of ethanol is −0.18 according to Wikipedia, i.e. in a two-phase system ethanol would preferrably accumulate in the aqueous phase, but not by much. Suppose I wanted to lower the alcohol ...
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Where will a H+ attack on 6-hydroxyhexan-2-one? [closed]

Where will a H+ attack on 6-hydroxyhexan-2-one? Protonation can take place either on the ketone or the alcohol. So where will it attack? In short, on which of the two oxygen atoms is electron density ...
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159 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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350 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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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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203 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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943 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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1answer
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How can aqueous KOH give alcohol by SN2 of alkyl halide?

I ask this because SN2 requires a strong nucleophile, and I have read $\ce{OH-}$ isn't a strong nucleophile in a polar protic solvent like water. So, how can $\ce{OH-}$ replace, say $\ce{I-}$ from $\...
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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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1answer
225 views

How to create 1-100 ppm ethanol gas?

I am trying to use TGS 2602 sensor of air contaminants. I would like to test if my circuit is working as intended. For that purpose I need to generate fumes of one of the gases the can be detected by ...
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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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461 views

Does cyclobutanol undergo acidic catalysed dehydration? [closed]

In an exam I had to find a substance X for the following reaction to be correct: $$\ce{X <=>[\ce{H2SO4}] Y + H2O}$$ I picked cyclobutanol. My teacher said cyclobutanol is wrong . Why?
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Does benzene react with steam to create an alcohol?

Benzene has a molecular formula of $\ce{C6H6},$ right? Surely it has some alkene-like properties because of the double bonds, so can it undergo a hydration reaction to create alcohol?
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What is reaction between isopropyl alcohol and acetone?

What would be the probable reaction between acetone, $\ce{(CH3)2CO}$, and isopropyl alcohol, $\ce{CH3CHOHCH3}$, at room temperature without any catalyst in different concentrations?
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Why is the reactivity of primary alkyl halides with nucleophiles (SN2 mechanism) greater than secondary and tertiary alkyl halides?

For the reaction between alkyl halide and a nucleophile, following the SN2 mechanism, the reactivity of alkyl halides is in the order: primary halide > secondary halide > tertiary halide. If you ...
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Solubility comparison of hexan-1-ol and cyclohexanol in water

Is hexan-1-ol or cyclohexanol more soluble in water? The answer is supposedly cyclohexanol. However, I found a statement in a book: Isomeric alcohols have solubilities in the order: primary alcohol ...
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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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638 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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565 views

How can I separate these two alcohols from each other out of the aqueous solution?

I have the following question for homework and am stumped. I am tasked with separating 3-(2-methoxyphenoxy)propane-1,2-diol and (1​R,2​S)-2-(methylamino)-1-phenylpropan-1-ol. They are both solvated in ...
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1answer
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Conversion of carboxylic acid to alcohol

Is it feasible to convert carboxylic acids to alcohols? I know the reverse is done during the oxidation of alcohols (e.g. in the production of vinegar), but is it possible to do it the other way round?...
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521 views

What is insoluble in drinking alcohol, but edible?

What substances are edible for human consumption, but will not mix with alcohol? What is a substance that would block alcohol from mixing with its counterparts in a product? For example: You make a ...

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