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.
558
questions
-2
votes
0
answers
45
views
What should be the major product of this reaction? [closed]
In this question, I am having confusion regarding the major product as all of them seem to be possible except option 3. What should be criteria to decide major product in questions like this where ...
- 17
0
votes
0
answers
56
views
What would be the correct IUPAC name of this compound? [duplicate]
How many carbon atoms will be there in the parent carbon chain? I have proposed its few names, which one is more appropriate?
4-Chloro-3-ethyl-2-(1-methylethyl)-butan-1-ol
3-(1-Chloromethyl)-2-(1-...
- 17
15
votes
1
answer
2k
views
What happens if you carbonate ethanol?
The electronics youtuber bigclivedotcom has an on-and-off-again series where he carbonates various types of alcohol and comments on the taste. One thing he's noticed is that the stronger the alcohol, ...
- 261
-2
votes
1
answer
84
views
Why does Methanol have a higher surface tension than Ethanol? [closed]
I am researching the surface tension of different alcohols and found something odd: the surface tension of Methanol was higher than that of Ethanol, which doesn't make sense to me. My understanding is ...
3
votes
2
answers
365
views
Flash point of naptha and propanol
I filled a Zippo lighter with 2-propanol and it lit up easily when the ambient temperature was around 6-7 degrees Celsius.
It was impossible to light it up when the temperature was around 3-4 degrees ...
- 139
-1
votes
1
answer
78
views
reaction of PCl5 with alcohol [closed]
I am able to think of two possible mechanisms for alcohol+PCl5 here, SN1 and SN2. In SN1, Inversion won't occur whereas, in SN2 inversion will occur. Which of the two is correct?
- 1
-1
votes
1
answer
38
views
Why is Quinone used, while oxidising primary alcohols by Oppenauer Oxidation, instead of Acetone? [closed]
Usually, during Oppenauer Oxidation, while oxidising secondary alcohols, acetone solution is used with Aluminium Tertiary Butoxide.
This results into the oxidation of secondary alcohol into a ketone, ...
- 1
0
votes
0
answers
18
views
Ion from unsaturated ether
As far as I am concerned, from unsaturated primary/secondary amines (enamines) we obtain imines, like we do obtain carbonyls from enols, by tautomerism. For tertiary enamines, we have a corresponding ...
7
votes
1
answer
162
views
Why don’t Grignard reagants react with their alcohol products?
I’ve read that Grignard reagants react pretty quickly with alcohols and carboxylic acids to form their respective conjugate bases. I’ve also learned that Grignards can be used for the prepararion of ...
- 79
2
votes
2
answers
65
views
Protonation in acid-catalyzed nucleophilic attack of alcohol on carbonyl
When studying acid-catalyzed nucleophilic attack of alcohol on carbonyl, I got puzzled by the first protonation step. In textbooks, they often show that the first step is to protonate the carbonyl ...
- 29
5
votes
1
answer
206
views
Mechanism for a reaction of reduced fluorophenol with BF3?
In the given question, $\ce{BF3}$ will act as an electrophile. Will it form $\ce{BF4-}$ and leave a positive charge on the carbocation to which $\ce F$ was attached or react with $\ce{OH}$. It will ...
0
votes
1
answer
62
views
How did you convert primary alcohol using HCl (with ZnCl2)?
I kinda feel weird for this type of question. When primary OH (alcohol) is converted with HCl (with ZnCl2), how did the free Cl-ion come from? If, it is came from HCl, since when we get rid of the H ...
- 1
2
votes
0
answers
37
views
Feasibility comparison of symmetric ether synthesis and HCl + alcohol SN2 reactions
According to Solomons & Fryhle 10$^{th}$ edition Ch 11.8,
Because the chloride ion is a weaker nucleophile than bromide or iodide ions, hydrogen chloride doesn't react with primary/secondary ...
- 328
4
votes
2
answers
147
views
Why does "bis-tris propane" have two pKa values?
Wikipedia gives two pKa values for "Bis-tris propane".
What about bis-tris-propane gives this compound two pKa values where other compounds have only one? How am I to choose which pKa value ...
- 151
2
votes
1
answer
239
views
Can someone explain the chemistry around adding Isopropyl Alcohol to water contaminated gasoline - how does the IPA 'remove' water from the gas?
So there are many products on the market sold as fuel additives; some (like 'Heet' brand) are nothing more than 99.9% isopropyl alcohol in a nice package.
When trying to understand how they work and ...
- 139
3
votes
1
answer
100
views
Does the ‘e’ from ‘-yne’ get dropped in compounds of higher functional groups?
What is the way of representing a triple bond in a compound of a higher functional group, like alcohol? Does the ‘e’ from ‘-yne’ get dropped like in the case of the ‘-ene’ suffix?
For example, would ...
- 355
3
votes
0
answers
34
views
How to calculate composition of alcohol/water mixture to achieve given concentration of alcohol vapors in air for calibrating a DIY breathalyzer?
I made a breathalyzer using a MiCS-5524 gas sensor. I would like to calibrate it so it can be close to accurate. e2v technologies — MiCS Application Note 4, Using MiCS Sensors for Alcohol Detection (...
- 31
-2
votes
1
answer
123
views
Oxidation of Methanol - how to write the half reaction
I am trying to write the half reaction equations for:
$$\ce{CH3OH + O2 -> HCOOH + H2O}$$
The primary goal for me here is to find out which reactant is oxidising without using prior knowledge of ...
- 105
-1
votes
1
answer
62
views
Why is it not possible for water to directly attach itself to the alkene to form an alcohol in oxymercuration? What is the need for mercuric acetate?
When going through the preparation of alcohols, I came across the method of Oxymercuration-Demercuration.
Now, after going over the reaction, I didn't understand the purpose of the mercuric acetate ...
2
votes
0
answers
32
views
Which 1,2-methylene shift is more favourable in ring expansions where ring has substituents
In the above reaction, first the -OH group is protonated after which it leaves creating a carbocation intermediate as shown
Now, ring expansion is a more favourable rearrangement, however there is a ...
- 139
2
votes
1
answer
48
views
What's a good high precision analysis technique (after GC) to measure trace isopropanol in water samples?
Looking to measure trace IPA content in water samples.
Only GC I have access to doesn't take samples with water. Different columns not an option.
- 31
0
votes
1
answer
73
views
Is formation of cyclic carbonate from trimethyl orthoformate and vicinal aromatic 1,2-diol possible? [closed]
Hello, my question is, "is it possible cyclic carbonate formation between trimethyl orthoformate and vicinal aromatic 1,2-diol"
-1
votes
1
answer
122
views
How is Magnesium Ethoxide appropriately prepared, stored and used to dry ethanol?
I found many procedures vaguely describing the preparation of magnesium ethoxide from elemental magnesium in excess dry ethanol in the presence of I2 as activator (in absence of air), I also know that ...
- 1,065
7
votes
1
answer
153
views
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 ...
- 140
1
vote
1
answer
55
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 ...
- 21
2
votes
0
answers
136
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 ...
2
votes
0
answers
208
views
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{...
user121185
-1
votes
1
answer
62
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-...
- 11
3
votes
0
answers
78
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 ...
- 101
1
vote
0
answers
113
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 ...
- 127
1
vote
1
answer
158
views
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 ...
- 21
2
votes
0
answers
295
views
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 ...
- 207
-1
votes
1
answer
250
views
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 ...
- 9
-1
votes
2
answers
127
views
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 ...
-1
votes
1
answer
691
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 ...
- 57
5
votes
1
answer
614
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)...
- 284
0
votes
1
answer
219
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?
user102173
0
votes
0
answers
347
views
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, ...
- 135
0
votes
0
answers
42
views
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 ...
- 217
-1
votes
1
answer
98
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 ...
- 9
1
vote
0
answers
43
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
vote
0
answers
38
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 > ...
- 101
1
vote
1
answer
71
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?
- 702
-3
votes
1
answer
123
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 ...
- 586
-1
votes
1
answer
108
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
votes
0
answers
143
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 ...
- 159
6
votes
1
answer
151
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
votes
0
answers
24
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 ...
- 31
8
votes
1
answer
317
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 ...
- 83
3
votes
1
answer
102
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 ...
- 99