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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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What is the expected trend in the evaporation rate of a mixture of alcohol and essential oil considering both are volatile? [on hold]

A volatile solvent and volatile solute mixture. Can you guide me to some studies that have literature values or that justifies why and whether the evaporation rate of these mixtures will increase or ...
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32 views

How do I draw a curly arrow diagram for the oxidation of primary alcohol to an aldehyde and subsequently to a carboxylic acid? [duplicate]

I've determined the chemical equations for both the mechanisms, but I'm unable to draw curly arrow diagrams for the two reactions using potassium dichromate as the oxidising reagent. I'm not sure how ...
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1answer
45 views

Ester of glycerol and glyceric acid

What is the ester of glycerol ($\ce{C3H8O3}$) and glyceric acid ($\ce{C3H6O4}$)? I couldn't find any information about it online, so is this reaction even possible? I'm not sure what would happen, ...
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1answer
43 views

Is 99% Isopropyl Alcohol sold in stores really 99%?

My understanding is that an azeotropic mixture of isopropanol and water is 91%. This makes sense as to why there are so many brands of rubbing alcohol sold at 91%. There are also some sold as 99%, ...
2
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1answer
35 views

Techniques to extract lipids

I am planning an experiment on how to isolate casein and part of the process involves removing any lipids that may still be in it after filtering the precipitated casein out of the milk. I have read ...
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0answers
31 views

Comparing acidity in 3,4-dihydroxyfuran-2(5H)-one and 2,3-dihydroxycyclopent-2-en-1-one

I have two compounds with two hydrogens namely (a),(b),(c) and (d). I have to compare the acidity of the following hydrogens. My approach: I removed the hydrogen atoms one by one and compared the ...
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1answer
43 views

Dependence of primary alcohol oxidation on presence of water and “strong” or “weak” oxidants

It is known that the oxidation of primary alcohols can result in aldehydes or carboxylic acids. The product obtained from the reaction is described as dependent on reagents and conditions;[1] "...
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1answer
46 views

Reaction of cyclobutylmethanol with HX

I am interested in the reaction of cyclobutylmethanol with HX where these are the only reagents. My question is whether the reaction proceeds via SN1 or SN2. My reference text insists that primary ...
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0answers
32 views

Ethyl Acetate and other Solvents in a mixture: miscibility and stability

I was wondering about a heterogeneous solvent mixture containing multiple alcohols such as IPA, Ethanol, methanol etc. Would EtOAc (Ethyl Acetate) play nice in these mixtures at low volumes such as 1 ...
4
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1answer
56 views

Chemical shifts of OH protons

The chemical shift of a proton is an indication of the amount of shielding it receives from the electron density on it or other magnetic anisotropy effects present in the molecule. For the protons of ...
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1answer
48 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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0answers
36 views

Should I use MCPBA here?

I came across a question that asked for a method to convert propene to glycerol. I used the method in the pic, but I'm worried about two steps- Step-2, This reaction is just made up by myself! I'm ...
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1answer
38 views

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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0answers
15 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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0answers
59 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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0answers
67 views

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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2answers
43 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
184 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 ...
3
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0answers
112 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
92 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
158 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
56 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
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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
152 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 ...
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1answer
147 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
189 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
41 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
86 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
67 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
93 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
3k 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
71 views

'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
118 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
96 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. ...
6
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1answer
740 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
1k 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
851 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
58 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
75 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 ...
3
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4answers
102 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
91 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
990 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
113 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
81 views

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
164 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
102 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
3k 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
529 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 ...