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.
522
questions
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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 ...
-1
votes
1answer
65 views
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 ...
1
vote
1answer
26 views
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 ...
1
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0answers
29 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 > ...
1
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1answer
26 views
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?
-3
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1answer
102 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 ...
-2
votes
1answer
51 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 ...
0
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0answers
47 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 ...
0
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0answers
18 views
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 ...
0
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0answers
49 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 ...
4
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0answers
66 views
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 ...
3
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0answers
21 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 ...
8
votes
1answer
144 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 ...
2
votes
1answer
79 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
votes
1answer
196 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 ...
4
votes
0answers
107 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 ...
5
votes
1answer
85 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 $S_\text N1$ ...
5
votes
1answer
84 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 ...
4
votes
1answer
118 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 ...
1
vote
1answer
214 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 ...
4
votes
2answers
274 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 ...
1
vote
2answers
63 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 ...
3
votes
2answers
110 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 ...
1
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1answer
102 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 $\ce{HSO4-}$...
12
votes
2answers
261 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 ...
1
vote
1answer
100 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 ...
3
votes
0answers
96 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 ...
3
votes
1answer
234 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 ...
7
votes
1answer
100 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 ...
0
votes
2answers
71 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 ...
1
vote
2answers
125 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 ...
0
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1answer
75 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 ...
3
votes
1answer
115 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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0answers
55 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 ...
4
votes
1answer
89 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
votes
1answer
237 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
votes
1answer
193 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 ...
1
vote
2answers
79 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 ...
3
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0answers
68 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
votes
1answer
174 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) ...
0
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0answers
52 views
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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0answers
48 views
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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0answers
30 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 ...
0
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0answers
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 ...
3
votes
1answer
269 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-...
2
votes
0answers
56 views
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 ...
2
votes
0answers
24 views
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 ...
0
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1answer
128 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. ...
0
votes
3answers
187 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'...
0
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0answers
113 views
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 ...
