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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Reaction between 1,2-bis(buta-1,3-dien-1-yl)cyclohexan-1-ol and potassium hydride in THF

Which product is formed in the following reaction? I am quite certain that we deal with an oxy-Cope rearrangement that works at room temperature, but I don’t know how to draw the product given the ...
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1 vote
1 answer
50 views

How is the intermediate compound 2-chloropropan-1,3-diol is formed when hypochlorous acid is added to allyl alcohol in the preparation of glycerol?

The expected product is 3-chloropropan-1,2-diol since secondary carbocation is more stable than primary but it is not formed. I have surfed the internet a lot regarding this and none seems to be a ...
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2 votes
0 answers
64 views

Can a hydroxyl group be attached to a triple bonded (sp hybridized) carbon?

Alcohols are defined as organic compounds containing one or more than one hydroxyl group attached to a sp3 hybridized carbon atom. And it is mentioned in the book I am referring to [errorless ...
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0 votes
0 answers
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Why don't secondary alcohols react with HBr/HI via SN2?

In polar protic solvents, $\ce{Br-}$ and $\ce{I-}$ are considered to be very good nucleophiles. Now, here the solvent is alcohol which is polar protic. So, why don't secondary alcohols react with $\ce{...
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-1 votes
1 answer
57 views

How to synthesize 1,1,1-trichloro-2,4-dimethylpentan-2-ol from methyl isobutyl ketone?

Chlorobutanol can be made with chloroform and acetone in the presence of potassium or sodium hydroxide. Would it work with other ketones such as methyl isobutyl ketone to yield 1,1,1-trichloro-2,4-...
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3 votes
0 answers
72 views

Acidification of a vicinal diol [duplicate]

The following is a question from Advanced problems in organic chemistry by MS Chouhan: The options given are: My initial thought was that this could be a pinacol–pinacolone rearrangement. However ...
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1 vote
0 answers
51 views

Comparison of boiling points between 2‐butanol and isobutanol

Which has higher boiling points among butan‐2‐ol (1) and 2‐methylpropan‐1‐ol (2)? I know that branching decreases the boiling points, but I want to know how position of substituents affects the ...
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1 vote
1 answer
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Reduction of unsymmetrical ketones using BINAL-H (Enantioselectivity)

I am struggling with a problem regarding the enantioselectivity of BINAL-H for quite some time now. The reaction scheme shows the reaction with (S)-BINAL-H as it is observed plus the transition state ...
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2 votes
0 answers
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Does yeast, sugar and water really produce any noticable/significant amounts of methanol?

I just read this question on Quora about distilling during pre-industrial age, which reminded me about multiple discussions I have heard or read during the years about whether the fermentation process ...
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-1 votes
1 answer
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Where in the apartment to store isopropyl alcohol

I want to have some 99% isopropyl alcohol for cleaning purposes and I'm wondering where to store it since in my apartment I don't have a storage room or much space. I've read it needs to be air tight ...
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-1 votes
2 answers
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Are intermediate bulk container units suitable for storage of isopropyl alcohol? [closed]

I'm working in water treatment construction and my boss is going to be stocking isopropyl alcohol (IPA). He wants to store the chemical in bulk, with amounts ranging from 5000 L to 10000 L in IBC ...
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-1 votes
1 answer
115 views

Which is more acidic alcohol or ketone? [closed]

I have read about it and i found that the alcohol is more acidic, but isn't the conjugate base produced from losing the alpha hydrogen of the ketone more stable ?! The negative charge in this ...
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5 votes
1 answer
313 views

Should the principal carbon chain contain maximum number of functional groups or just the principal functional group?

My answer was the 6 carbon chain, i.e. the name would be 2-(2-hydroxyethyl)-4-methylhexanoic acid. But the given answer is the 4 carbon chain, i.e. the name would be 4-hydroxy-2-(2-methylbutyl)...
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Can I use Ethanol in place of Isopropyl Alcohol in the DNA Isolation Experiment?

I am performing an experiment on the DNA isolation of strawberries. This article, asks us to use Isopropyl alcohol. I do not have Isopropyl alcohol at the moment so would it be alright if I use ...
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0 votes
1 answer
158 views

Selectivity in dehydration of isopropyl alcohol to diisopropyl ether

Can isopropyl alcohol be dehydrated by sulfuric acid to diisopropyl ether in a similar way as to how ethanol can? Is there a way to avoid or at least minimize the inevitable dehydration to propylene?
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Why 1-methylethanol is not preferred IUPAC name for isopropyl alcohol?

For the compound $\ce{CH3-CH(OH)-CH3}$ I propose two names: propan-2-ol and 1-methylethanol. Which is the correct name as per the IUPAC guidelines? According to Organic Chemistry by Morrison and Boyd, ...
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0 votes
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Solubility of multiple solutes and limits of solubility during freezing

I'm interested in modeling the freezing of solutions of water and I'm not really sure what happens in water after the solubility of a given material is reached. I know that as ice crystals form they ...
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-1 votes
1 answer
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What is the product when alcohol is added to carbonyl compounds? [closed]

How do we know if, on adding alcohol to carbonyl compound: nucleophilic addition reaction will take place or alcohol will take alpha hydrogen to form a carbanion and consequent aldol condensation ...
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1 vote
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Polarity vs Acidic Strength (Alcohols and Inorganic acids) [closed]

If $\ce{HI}$ is more acidic than $\ce{HCl}$ because less polarity in $\ce{H-I}$ makes it easier to donate $\ce{H+}$ ion thus increasing its acidic strength, how does more polarity in $\ce{O-H}$ bond ...
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1 vote
0 answers
32 views

How can we say that one reaction is faster than another if two conflicting factors are at play in both of them

While learning about the preparation of alkyl halides from alcohols by reacting them with hydrohalic acids, it was mentioned that the order of reactivity of different alcohols is Tertiary > ...
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1 vote
1 answer
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Would TFA be a strong enough acid to perform an SN1 reaction on alcohols?

The pKa of sulfuric acid, which is usually used to do this reaction is -3, but would TFA be sufficient even though it has a pKa of 0.5?
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-3 votes
1 answer
110 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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-1 votes
1 answer
62 views

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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0 votes
0 answers
59 views

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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0 votes
0 answers
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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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0 votes
0 answers
80 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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4 votes
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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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3 votes
0 answers
23 views

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 ...
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8 votes
1 answer
176 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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3 votes
1 answer
86 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 ...
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4 votes
1 answer
254 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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4 votes
0 answers
126 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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5 votes
1 answer
104 views

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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5 votes
1 answer
144 views

When does reaction of alcohol with alumina give an ether and when an alkene?

What is the main product when an excess of ethyl alcohol vapour is passed over heated alumina at 250 °C? I read that this reaction gives an ether (here, diethyl ether) at relatively lower temperature ...
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5 votes
1 answer
176 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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  • 141
1 vote
1 answer
342 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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  • 115
4 votes
2 answers
388 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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  • 141
1 vote
2 answers
119 views

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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3 votes
2 answers
138 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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1 vote
1 answer
143 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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12 votes
2 answers
313 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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1 vote
1 answer
154 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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3 votes
0 answers
99 views

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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2 votes
1 answer
289 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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  • 154
7 votes
1 answer
126 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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0 votes
2 answers
75 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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  • 154
1 vote
2 answers
189 views

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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0 votes
1 answer
124 views

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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3 votes
1 answer
122 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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0 votes
0 answers
58 views

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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