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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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Acid catalysed dehydration of unsymmetric alcohols

How to find the major product of acid catalysed dehydration of unsymmetric alcohols. For example, in the dehydration of butan-2-ol using conc. H2SO4, which is the major product? But-1-ene or But-2-ene?...
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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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0answers
55 views

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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Dehydrogenation/Dehydration of alcohol with Cu

When the vapours of a 1°,2°,3° alcohol are passed over red hot Cu powder at 573K, 1°,2° alcohol undergo dehydrogenation to form an aldehyde or ketone respectively and 3° alcohol undergoes ...
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1answer
7 views

Where will the positive charge shift in the E1 mechanism of dehydration of an alcohol? [closed]

My Attempt: according to me the double bond should be in position no. 2 but the correct answer has a double bond in position no.1. Why is it so? Thanks in advance.
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0answers
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Measuring alcohol content using a Gay Lussac aclohol meter

I am trying to determine the alcohol content of a home brewed beverage; I only have a Gay-Lussac alcohol meter at my disposal. From my understanding, the Gay-Lussac degree will be accurate only at the ...
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2answers
40 views

Acetal Formation Mechanism

In this example, why is there is a ring formation with the attack of the OH from the intermediate itself rather than a continuation of addition? I know my proposed product is wrong, however I just ...
3
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2answers
135 views

The intrinsic electron-withdrawing nature of alkyl groups

What you are about to read may be a very mind-boggling paragraph but please do not regard it as nonsense. Please think through it thoroughly. In Chapter 6 of Organic Chemistry (4th ed.) by Maitland ...
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0answers
91 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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0answers
51 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
94 views

Is cyclohexanol or hexanol more acidic?

If we had a hexane ring with an $\ce{OH}$ substituent vs. a hexane chain with an $\ce{OH}$ substituent, which of the two, if any, would result in a weaker conjugate base? My confusion: The ring ...
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1answer
50 views

Protection of Alcohol

I carried out an experiment and it goes like this: 2-bromoethanol + dihydropyran (DHP) ---> 2-(2-bromoethoxy)oxane Acidic ion exchange resin was added alongside as a source of H+ ions (catalyst). ...
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3answers
4k views

Evaporation of isopropyl alcohol [closed]

Does evaporation of isopropyl alcohol at room temperature leaves residue? and why it is able to evaporate although it does not reach its boiling point?
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1answer
105 views

Are secondary alcohols more easily oxidised as compared to phenol?

Which among the following compounds is oxidised most easily? 2-propanol ($\ce{CH3CHOHCH3}$) phenol ($\ce{PhOH}$) ethoxyethane ($\ce{Et-O-Et}$) 1-methyl cyclohexanol The answer given ...
3
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1answer
95 views

When does a pinacol undergo dehydration or rearrangement?

What happens when the above pinacol is treated with - (a) conc. sulphuric acid (b) dil. sulphuric acid I'm confused between pinacol rearrangement and dehydration (E1 or E2?), as both possibilities ...
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0answers
85 views

Why does IPA turn cloudy when added to water?

When I pour isopropyl alcohol into water (tap water not distilled water), it turns cloudy. I’ve heard that alcohol is miscible with water (the the liquids should not give a precipitate) . Also, what ...
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0answers
36 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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1answer
75 views

Why are lower alcohols less flammable than their corresponding alkanes?

How to compare the general trend in amount of combustion in lower alcohols? (upto five/six carbons) Does the branching or straight chain have any effect on combustion?
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1answer
61 views

Rearrangement of 8a-ethyl-1,3,4,8a-tetrahydronaphthalen-4a(2H)-ol [closed]

really sorry for that previous post. I was actually half-asleep when I posted that q, hence the q was unclear. I am again reposting that question The answer is given as A. Can anyone please explain ...
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2answers
71 views

Reaction involving opening of epoxides

The following question was asked in an exam today: I chose the option (a), but the correct answer given was (b). Following is the explanation why I chose (b): Step 1 (Reaction with $\ce{PBr_3}$): $...
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1answer
2k views

What is an aromatic alcohol?

The following question was given in NCERT Exemplar Problems (Class XII): According to Wikipedia: In organic chemistry, the aromatic alcohols or aryl-alcohols are a class of chemical compounds ...
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1answer
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'Alcohol Free' toiletries

Sometimes I see 'alcohol free' written in big letters on toiletry bottles, such as on deodorants and shaving foams. You would think that the toiletries bearing these words contain 100% no alcohol, ...
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2answers
97 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
93 views

How is more than one pinacolone is possible?

This question came in one of my school tests. They had given us an unsymmetrical pinacol i.e 1,1-diphenyl-2-methylpropane-1,2-diol and asked us whether it will give only one pinacolone or not. ...
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1answer
490 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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2answers
687 views

Why ethanol doesn't react with NaOH ,while methanol does? [duplicate]

Why ethanol doesn't react with NaOH ,while methanol does?
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1answer
568 views

What are the products of the reaction of methoxypropane with HBr?

The products of the reaction of methoxypropane ($\ce{CH3CH2CH2OCH3}$) with $\ce{HBr}$ are? In my opinion, the products should be: bromopropane ($\ce{CH3CH2CH2Br}$) + methanol ($\ce{CH3OH}$). The ...
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0answers
52 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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3answers
53 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 ...
2
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1answer
74 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
86 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
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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
682 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
82 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 ...
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0answers
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Change of properties from Propanol to Butanol [duplicate]

This might be a silly question, but I couldn't find a nice answer. Reading the properties of short alcohols I found some data and made this table: PS: I apologize for the footnotes. S= solubility. ...
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1answer
124 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
86 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
2k 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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2answers
432 views

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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0answers
42 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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2answers
2k views

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
187 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
116 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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0answers
179 views

How does an alcohol's chain length influence it's miscibility with organic solvents?

Recently someone asked a question about ethanol in fuel. This got me thinking about the miscibility of ethanol in different compounds. I know ethanol and water mix infinitely well due to the ...
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1answer
371 views

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
45 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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170 views

Ease of dehydration of mono-hydric alcohols

Which of the following would undergo dehydration most readily? (i) 2-phenyl butan-2-ol (ii) 1-phenyl butan-2-ol (iii) 2-phenyl butan-1-ol Ease of dehydration depends on the stability of carbocation ...
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2answers
309 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
94 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
311 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 ...