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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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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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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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
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1
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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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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
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0
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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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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 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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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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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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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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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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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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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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2
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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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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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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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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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2
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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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2
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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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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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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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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 ...
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2
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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 ...
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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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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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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 ...
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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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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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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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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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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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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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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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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.
...
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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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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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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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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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Why does Ethylene Glycol have higher boiling point than Propylene Glycol?
Looking at the two alcohols, both have hydrogen bonding and are singly bonded throughout the molecule. However, propylene glycol has a larger electron cloud which to my knowledge would increase its ...
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Is it safe to mix methylated spirits with isopropyl alcohol?
I have about 200ml of methylated spirits and 500ml of 100% isopropyl alcohol that I want to mix together in a plastic drink bottle. I will use it for fuel in an alcohol burning stove while camping. ...
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2
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Is 6-ethenyl-4-(prop-2'-enyl) octa-6-en-3-ol a valid name?
I recently study organic chemistry and I read a book by Sana Jamshaid. I came across this compound and I cannot understand why it named 6-ethenyl-4-(prop-2'-enyl) octa-6-en-3-ol:
I understand that ...
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Why does the C−H bond dissociation energy vary in a homologous series of primary alcohols?
Specifically, for the primary carbon atom in the alcohol. Here is bond dissociation energy (BDE) data from chapter three of Luo's Comprehensive handbook of chemical bond energies [1] (boldface refers ...
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Red Compound from Glycine and Glycerol?
I got an unexpected reaction which I'm trying to explain to myself:
I mixed 10 parts glycerol with 1 part glycine at ~90C and to my great surprise the mixture turned from transparent to a tint of red. ...
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