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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90 views

Why is Denaturated alcohol made poisonous? [closed]

I understand the need to denaturate alcohol, as to have a material that can be used for non-food products without the heavy alcohol beverage tax. So, adding a foul tasting bitter substance like ...
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1answer
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Does Fischer esterification occur when mixing alcoholic drinks with lemon juice?

I would assume it does happen because the ethanol in the drink would be in an acidic environment because of the lemon juice and would react with the citric acid in it. But the thing is, how come we ...
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Converting Newman projection to dash and wedge structure

I want to convert the following Newman projection to a dash and wedge structure but the examples I've seen online are with simple molecules with methyl groups on the side. I wanted to show the long ...
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0answers
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suffix in IUPAC nomenclature [duplicate]

The name of the following of compound is given as propane-1,2,3-triol. HO-CH2-CH(OH)-CH2-OH The structure and nomenclature is very simple for this compound (C3H8O3) but my doubt is why propane does ...
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42 views

Major product in the reaction of alcohol with unsymmetrical acid anhydride

When alcohol reacts with symmetrical acid anhydride to form ester. We have the following reaction, But if the acid anhydride used is unsymmetrical how can we identify the major product? For example ...
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Acidity of alcohols

So everywhere that I've read, there's the reasoning that the acidity of a compound is determined by how stable the conjugate base is, this should be the same for alcohols too, but on Chemistry ...
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0answers
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Conversion of allyl alcohol to 2-chloro propanediol with HOCl [duplicate]

going through the preparation of tri hydric alcohol(glycerol), i came across this reaction i.e. preparation of glycerol from propene. In the first step of this reaction, we did allyl substitution with ...
8
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1answer
128 views

Why does LiAlH4 reduce the double bond of cinnamaldehyde, whereas it does not reduce the double bond in crotonaldehyde?

$\ce{LiAlH4}$ is a strong reducing agent capable of breaking the double bonds. It does break the double bonds in cinnamaldehyde. Shouldn't $\ce{LiAlH4}$ be able to break the double bond in ...
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1answer
75 views

Dehydration reaction of an alcohol, 2,3-dimethyl-2-phenylbutan-1-ol, with conc. sulfuric acid (at high temperature)

What's the major product of the dehydration reaction of 2,3-dimethyl-2-phenylbutan-1-ol with conc. $\ce{H2SO4}$ (at high temperature)? I am aware that in this reaction $\mathrm{E}$1 mechanism will be ...
4
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1answer
172 views

dehydration of an alcohol (3-methyl-1-phenylbutan-2-ol)

I was thinking of dehydrating this alcohol: 3-methyl-1-phenylbutan-2-ol Its structure is: My concern is which of the following would it form: The problem is that the first one comes from a stable ...
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98 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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1answer
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What is role of copper powder, calcium chloride and cuprous chloride in the SN1 reaction of hydrochloric acid with propargylic alcohol?

For the synthesis of a 2H-cromene from a phenol I need to prepare 3-chloro-2-methyl-but-1-yne from the corresponding alcohol 2-methylbut-3-yn-2-ol. This reaction could be seen as a simple $S_\text N1$ ...
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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
78 views

Why does a methyl shift occur during the pinacol-pinacolone rearrangement?

Why does a methyl shift occur during the pinacol-pinacolone rearrangement? I was told that methyl shift is done to stabilise the carbocation but here we are shifting the ...
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1answer
167 views

What is the product of the reaction between alcohol and acetyl chloride in presence of pyridine?

What happens when butan-2-ol reacts(under heat) with $\ce{CH3COCl}$ in the presence of pyridine? Does it form $\ce{CH3COOCH(CH3)CH2CH3}$? I got the ester mentioned but the solution says it gives an ...
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2answers
229 views

Why and how does ring expansion occur in the dehydration of (cyclobut-3-ene-1,2-diyl)dimethanol?

Can someone explain how does this ring expansion occur with the mechanism? I do understand that the hydride shift occurred because of carbocation stability but why did the ring expand? Can you please ...
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2answers
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Preparation of Alcohols from Grignard Reagent

We were given this question in the class: Answer given: I got 2-Methyl Butanol. Why doesn't the methyl attack the 2nd carbon atom from the oxygen atom and form 2-Methyl Butanol instead of attacking ...
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2answers
74 views

Predicting product ratio by rearrangement in Dehydration Reactions

I came across this question recently, which would have a clear major product. The OP has given satisfactory explanation for the product ratio, but wasn't sure about the major product. When I was ...
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1answer
94 views

Major product of the dehydration of alcohols

Well I was doing some questions and I have a bit of confusion on dehydration reaction. For instance, consider following reaction: How do I decide which adjacent hydrogen gets attracted by $\ce{HSO4-}$...
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1answer
180 views

Do azeotropic mixtures evaporate proportionally?

Do azeotropes evaporate, without boiling, in proportionate amounts, or does this property describe their behaviour only at boiling point? Concretely, if 91% isopropyl alcohol/water (by volume, i.e. an ...
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1answer
82 views

why doesn't alcohol react with sodium hydroxide but react with potassium hydroxide? [closed]

I have read that ROH+ NaOH doesn't form alkoxide ions because water is a stronger acid than all alcohols except methanol. However while reading xanthate test I found that alcohol reacts with KOH to ...
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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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1answer
208 views

Rearrangement in dehydration of alcohol

I came across the following problem in my book: Now my confusion is how will cyclohexene be obtained? I read that primary alcohols dehydrate by E2 mechanism because of formation of a primary ...
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1answer
89 views

Does a reaction proceed through SN1 if rearrangement results in a stable carbocation?

While going through my book I came across the following problem: I thought it was safe to assume that the secondary alcohol would give SN1(although secondary alcohols give significant amount of both ...
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2answers
66 views

Confusion regarding mechanism of dehydration of alcohols [closed]

1)Today I came across a problem which asks to find the order of dehydration of 2-hydroxycyclohexanone(1), 3-hydroxycyclohexanone(2),4-hydroxycyclohexanone(3). The answer is 2>3>1 But I thought ...
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2answers
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Intramolecular Cannizzaro reaction product

I came across the following question : My reasoning was as follows : It can't be option (c) because there is no chance of losing a carbon during Cannizzaro's reaction It can't be option (b) because ...
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1answer
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Methanol-water mix freezing points - clarify contradictory online data > 60% w/w?

Extending an exploration of windshield washer-fluid choices to freezing points of methanol-water mixes, all web-sources located agreed to within a couple of degrees from 0-60% w/w, yet above this ...
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1answer
110 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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Is my bottle of "RooR"-brand glass cleaning liquid pure isopropyl alcohol or something else?

I have this exact bottle: https://www.grasscity.eu/media/catalog/product/cache/2b55fa971a29a7844993ad77b24950ac/i/m/img_3633_1_1.jpg I originally purchased it to clean my vaporizer (I've since stopped ...
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1answer
66 views

On the molybdenum(III) oxide-catalysed oxidation of alkanes to carbonyls

The following reaction is specified in my notes; $$\ce{CH4 ->[Mo2O3, \Delta]HCHO}$$ The intermediate steps involve the dehydration of an alcohol to yield the final product. Wouldn't this only work ...
2
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1answer
165 views

Periodic acid oxidation of carbonyls?

The following reaction seem to be valid; $\ce{CH2OH-CHOH-CH2OH ->[HIO4]CH2O + HCOOH + CH2O + 2H2O}$ Apparently, there are similar reactions by 2,3-dihydroxypropanal, and also by the straight chain ...
5
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1answer
162 views

Why there is a color fading ( to colorless) when Cerium Ammonium Nitrate (CAN) is mixed with ethanol or butanol? [duplicate]

I have mixed CAN in butanol and also ethanol (separately), the solution became dark red immediately but after a couple of minutes the color totally faded and turned into a transparent solution, I am ...
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1answer
56 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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0answers
58 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 ...
2
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1answer
167 views

IUPAC name of cyclopentanol derivative

Is the name of the following compound 3-(ethenyl)-5-(prop-1-enyl)-2-(prop-1-ynyl)-4-(prop-2-enyl)cyclopent-2-en-ol? The problem I am facing is that how do I arrange 5-(prop-1-enyl), 2-(prop-1-enyl) ...
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Possibility of removing two water molecules from glycerol

Not a chemist, but from a chemical formula perspective, how hard would it be to create acetone by acidifying glycerol? $$\ce{C3H8O3 + 2 H+ <=> C3H6O + 2 H2O}$$ Has anyone ever heard of this ...
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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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41 views

Reaction between phosphorus(III) bromide and alcohol

Alcohol acts as a nucleophile in a reaction with $\ce{PBr3}.$ It attacks the $\ce{PBr3}$ leaving $\ce{Br-}$ behind. The alcohol forms a bond with the $\ce{PBr2+}.$ How the oxygen having three bonds ...
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1answer
229 views

What is the IUPAC name of this organic compound? [closed]

Variety is the spice of life. I have made an organic compound myself. Can you please tell me the name? I thought that the correct answer is - 3,3-dibromo-2,4-dichloro-1,4-difluoro-2,4-diiodo-1-...
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0answers
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Show the mechanism of the Pinacol-Pinacolone Rearrangement reaction [duplicate]

In the reactant, due to $\ce{H+}$ ion, a positive charge will be created by removing water in place of the rightmost $-\ce{OH}$. But then how will it give such a product. I cant see any way to make ...
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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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1answer
110 views

Sodium and alcohol reaction

I wonder, what happens when sodium reacts with alcohol? What is the reaction mechanism? I think that sodium is an electrophile that attacks the nucleophile oxygen atom in the -OH-group of the alcohol. ...
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3answers
148 views

How to verify that ethanol is infinitely soluble in water?

My textbook [Chemistry Live, Declan Kennedy] states that ''Ethanol is said to be infinitely soluble in water''. It then says ''verify this for yourself by mixing some ethanol with water in a test tube'...
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Base/acid reaction -> alcohol amphoteric? why no pkb value?

I have a question concerning acid/base reactions. Is it true that an alcohol is a better base than water? My Professor listed the basicity (because we talked about E1/E2 and Sn1/Sn2 reactions) of the ...
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1answer
748 views

Major product in dehydration of alcohol

Consider the dehydration of the following molecule with conc. $\ce{H2SO4}$ at $443 \text K$: The possible products are: The first one is the Zaitsev product and the second one Hofmann product. ...
4
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1answer
185 views

Intermolecular forces of attraction between positional isomers of alcohols

This seemingly trivial question is as follows: Why is the boiling point of 1-butanol ($\ce {117.7 ^\circ C}$) higher than that of 2-butanol ($\ce {99 ^\circ C}$)? The only reason I can think of is ...
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2answers
151 views

When does Alcohol act as Solvent and as a Nucleophile?

I was recently solving problems related to Alcohol. and its solution is My doubt is why methanol act as a nucleophile here and when does alcohol acts as a nucleophile and as a Solvent?
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364 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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0answers
61 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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