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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4
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1answer
409 views

Hydrolysis of an ester

An organic compound X of formula $\ce{C5H10O2}$ forms two compounds when boiled in aqueous sodium hydroxide solution. One of these compounds forms a ketone when treated with acidified potassium ...
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1answer
241 views

The need for excess acid in dehydration of alcohols

Why is there a need to use excess acid in the dehydration of alcohols? My instructor said that excess acid is necessary to minimize the ether formation via the competing SN2 mechanism, but I'm not ...
4
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1answer
6k views

What is the chemical equation for wine fermentation?

I am researching about the impact of sugar on wine fermentation, so I am looking for the equation of that reaction. However, there are a few different versions from different sources, so I was ...
6
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1answer
90 views

Why can alkoxides leave in the E1cb mechanism?

Why can alkoxides leave in the $\text{E}_{\text{1cb}}$ mechanism? I refer to the mechanism below. I would think that the anion formed from the first step would be more stable than the alkoxide ion, ...
2
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0answers
1k views

Is 70% ethanol hygroscopic?

I'm currently doing some DNA extractions and I realized that in some protocols, they are saying that ethanol is hygroscopic. In this source, they are saying: 85% ethanol made with nuclease free ...
2
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1answer
381 views

Selectivity in acetonide formation from a polyol

In my total synthesis lecture notes the above example is given in which a polyol is reacted under acetonide forming conditions. The notes point out that this product is the only product, no other ...
0
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2answers
1k views

Esterification with tertiary alcohol

I saw a different mechanism for esterification of tertiary alcohol in a book. They say that first the $\ce{OH}$ is protonated and it leaves to form the tertiary carbocation. Then the oxygen's lone ...
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1answer
2k views

Action of conc H2SO4 on pinacol [closed]

Question: Please suggest the correct answer along with suitable mechanism
6
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1answer
62 views

Effect of Base on E2 product

One base is bulkier than the other, that's my observation. How does it affect the product? Could someone please give proper reasoning and the product? Thanks a lot. P.S. I guess both follow E2
0
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0answers
85 views

Why is triethyl orthoformate stable? [duplicate]

Geminal diols or triols are very unstable and are easily converted into keto or carboxylic compounds. Triethyl orthoformate is a triether of similar structure. I want to know why the former is so ...
2
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1answer
5k views

Do secondary alcohols prefer to undergo SN1 or SN2 reactions when reacting with a strong acid?

For example, let us say we have 2.2-dimethycyclohexanol reacting with $\ce{HBr}$. We know that the oxygen gets protonated and then leaves as water, but the question does it leave on its own or does a ...
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0answers
256 views

Parts Per Million

I am trying to calculate how many milliliters of a solution I cannot exceed to create $\pu{200ppm}$ in the air of isopropyl alcohol. The $\pu{26ml}$ bottle of solution is 70% isopropyl alcohol. Using ...
2
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1answer
4k views

How can aqueous KOH give alcohol by SN2 of alkyl halide?

I ask this because SN2 requires a strong nucleophile, and I have read $\ce{OH-}$ isn't a strong nucleophile in a polar protic solvent like water. So, how can $\ce{OH-}$ replace, say $\ce{I-}$ from $\...
8
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1answer
922 views

Treatment of allylic alcohol with thionyl chloride: why is the product rearranged?

I have read that $\mathrm{S_Ni}$ reactions involving the attack of $\ce{SOCl2}$ on alcohols proceed without the formation of discrete carbocations, and hence there is no rearrangement involved. But ...
6
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1answer
596 views

Treatment of 2-vinylbicyclo[2.2.2]oct-5-en-2-ol with potassium hydride

What happens when this bicyclic compound is treated with KH in THF? Does $\ce{KH}$ simply act as a base here? $\ce{H-}$ from $\ce{KH}$ could potentially act as a nucleophile, but I don't find any ...
7
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1answer
644 views

What will be the possible major product(s) on heating this primary alcohol i.e. 9-fluorenylmethanol with (conc) H2SO4?

When the above compound is heated with (conc.) $\ce{H2SO4}$ the $\ce{OH}$ will probably be protonated and it will leave, producing a carbocation. After that possibly there will be a hydride shift. Now,...
3
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1answer
129 views

Adding ethanol to louche

I'm watching MIT chemistry by Donald Sadoway. In one of his lectures devoted to solutions and phase separation, he performs experiments with absinthe. First he mixes absinthe with 5 $\times$ water ...
4
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1answer
993 views

Oxidation of tertiary alcohols

Why is it that tertiary alcohols cannot be oxidized? I was told that it's because there is no hydrogen to remove, but I don't understand why another OH could not be formed where there is a C-H bond.
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0answers
597 views

Are esters and amides soluble in cold acids/bases? [closed]

The main problem I have is that we say amines are soluble in acids because they are bases, and they will thus react with acids. But if A reacts with B, how does that imply A is soluble in B? Yes, ...
7
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1answer
491 views

Does “soluble in alcohol” imply ethanol?

Sources like Wikipedia and SolubilityOfThings say that copper (II) acetate is soluble in alcohol. Does that mean any alcohol, or does "alcohol" in this context mean ethanol?
2
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0answers
171 views

Acid-catalyzed epoxide opening

For the acid catalyzed opening of epoxides, the epoxide is first protonated to form the oxonium ion. I read in some textbooks that the $\ce{H2O}$ molecule, which acts as a nucleophile attacks in a $\...
14
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1answer
799 views

Can we synthesize alcohols by the photolysis of hydrogen peroxide?

As I was going through my revision of organic chemistry, I came across free radical substitution of alkanes with halogens. In a similar process where we use hydrogen peroxide, instead of chlorine, so ...
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0answers
5k views

How to make a primary alcohol from an alkane?

Alcohols can be made from alkyl halides, which can be made from alkanes. However $3° > 2° > 1° > 0°$ for alkyl halides synthesis from alkanes. What approach could make an alkane with primary ...
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0answers
4k views

What is the mechanism of reaction between alcohol and PCl5 [closed]

Is this one correct? If not why and what is the correct one?
4
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1answer
726 views

Why doesn't the oxidation of cellulose oxidise all the alcohol groups, and how does it cause discolouration?

In cellulose, there are several alcohol groups - the two on the ring being secondary alcohols, and the one on the branch being a primary alcohol. I would expect all of these to be oxidised in the ...
3
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3answers
6k views

RO (alkoxide) as a leaving group

Why is RO (alkoxide) a better leaving group than OH, despite RO being more unstable due to the electron donating effect of the alkyl group on RO? I read that the suitability of leaving groups is ...
1
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1answer
228 views

Dehydration of alcohol

I have seen $\ce{P4O_{10}}$ and $\ce{HSO3Cl}$ being used to dehydrate carboxylic acids giving an anhydride and a ketene respectively. Can we use them to dehydrate $\ce{-OH}$ (of aliphatic alcohol) ...
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2answers
5k views

Why alcohol is volatile although it has hydrogen bonds?

We are always told that hydrogen bonds increase the boiling point of a liquid and as a result they decrease the liquid's volatility. I want to know the reason why, alcohol with hydrogen bonds is ...
3
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1answer
3k views

Can a product be alcohol free while containing isopropyl myristate or isopropyl palmitate?

I always find isopropyl myristate and isopropyl palmitate in cosmetics, and I want to know if they have alcohol in them or not. I read that they are composed of alcohol and acid, but they are ...
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0answers
107 views

How to write a reasonable mechanism for the reaction of alcohols to synthase ketone?

In the section of reactions of alcohols in my textbook, there are no mechanisms or explanation for this reaction: I am interested in Jones Oxidation particularly. I researched a little bit on ...
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1answer
1k views

Rate of reaction with HBr [closed]

Rate of reaction is more when Carbon is more electrophile(less electron density) So according to me the order should be D>B>C>A As NO2 has -M -I effect , Cl has +M -I effect , while OCH3 has +M -I ...
5
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1answer
450 views

What stops intermediates of alcohol hydration and dehydration reacting in the same way?

I am aware they both occur under different conditions and that water attaches in a secondary position in elimination but primary position in hydration. (Stage 2) (Stage 3) But both appear to be ...
2
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1answer
1k views

Why do esters have to be distilled during purification?

I am currently designing a lab experiment for a school project in which I am to determine the effect of catalyst concentration ($\ce{H2SO4}$) on the rate of reaction between methanoic (formic) acid ...
0
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2answers
97 views

lowest energy conformation of butan-2,4-diol

Do the OH groups want to be furthest apart? or the CH3 groups? I'm trying to determine the lowest energy conformation - and I don't know which group has the bigger steric effect?
0
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2answers
594 views

How does alcohol keep smell and taste flavors in wine?

Nowadays alcohol free wine is also sometimes available. Now is seems that this wine has less taste and flavors in it. The cause for this is that alcohol seems to the capability to keep these flavors ...
1
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1answer
64 views

Do the letters ol in a substance only indicate that the substance is an alcohol if they came at the end of the name of a substance?

Do the letters ol if they are together only indicate the substance is an alcohol if they come together at the end of the name of a substance? for example,is glycerol an alcohol because the letters o ...
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1answer
85 views

Required alkenes and reagents for alcohol products [closed]

In the reactions of alkene, which alkene and reagents would be necessary to produce 2,3-dimethyl-2-butanol 3-bromo-2-methylbutan-1-ol For 2,3-dimethyl-2-butanol, I came to the conclusion that it ...
8
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2answers
14k views

Polarity of alcohols and their miscibility in water

I am an AP Chemistry student and there is a small detail concerning polarity of molecules that I am confused about. My review book (Princeton review) says that ethanol has stronger intermolecular ...
7
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2answers
613 views

Retrosynthesis of a lactone

We have been asked to do a retrosynthesis of (6⁠S)-6-[(2⁠S)-2-hydroxy-4-phenylbutyl]oxan-2-one J from 3-phenylpropan-1-ol K: My first instinct would be to do a functional group interconversion of the ...
2
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0answers
3k views

Will oxalic acid react with ethanol?

Will oxalic acid, in a saturated solution in ethanol, be able to undergo an esterification reaction with the ethanol? This is assuming no acidifying agents (or anything else, for that matter) are ...
5
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1answer
636 views

Why is 1,3-pentadiene favored in the reaction of pent-3-en-2-ol with sulfuric acid?

Let's say we have the following reaction, a simple dehydration reaction. Why do we get 1,3-pentadiene and not 2,3-pentadiene?
7
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1answer
2k views

Which of the following para-substituted benzyl alcohols reacts fastest with HBr?

I had a question in a recent test which asked me to pick the compound that would react fastest with $\ce{HBr}$ with the options being: p-nitrobenzyl alcohol p-chlorobenzyl alcohol benzyl alcohol p-...
4
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2answers
4k views

Reaction of ethylene glycol with PI₃ (P + I₂)

We know that $\ce{2P + 3I2 -> 2PI3}$ Ethylene glycol reacts with $\ce{PCl3}$ to give ethylene dichloride, but why does it gives ethylene when it reacts with $\ce{P + I2}$? I don't really know ...
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4answers
2k views

Why n-Butanol is not used as a safer alternative to ethanol in the alcoholic beverages?

The $LD_{50}$ of n-Butanol adjusted for its intoxicating potency is about 1.5 times that of ethanol. This would mean to me that n-Butanol is therefore 50% safer than ethanol. Why is it not used to ...
1
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1answer
80 views

Why does a carbonyl group form instead of alkene in alcohol oxidation?

I am looking over mechanism of the oxidation of alcohol by chromic acid and I am confused on why $\ce{H2O}$ abstracts hydrogen from alpha carbon and form double bond between $\ce{C}$ and $\ce{O}$ atom ...
1
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2answers
627 views

How can I separate these two alcohols from each other out of the aqueous solution?

I have the following question for homework and am stumped. I am tasked with separating 3-(2-methoxyphenoxy)propane-1,2-diol and (1​R,2​S)-2-(methylamino)-1-phenylpropan-1-ol. They are both solvated in ...
2
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1answer
1k views

Correction formula for alcoholmeter

I need to find the formula, if there is one, which would calculate the correction of alcoholmeter. Basically convert observed %ABV (Alcohol by volume) to actual %ABV using the sample's temperature. ...
1
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1answer
345 views

Nucleophilicity of alcoxy groups

I found a nucleophilicity order as $\ce{HO-} > \ce{CH3-O-} > \ce{(CH3)2CH-O-} > \ce{(CH3)3C-O-}$ The reason was given that bulky groups reduce nucleophilicity. But why? The order of the $+...
1
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1answer
4k views

Water with Sodium VS Alcohols with Sodium

Why is the reaction between water and sodium more vigorous than that between ethanol and sodium? Also, why does the reaction between sodium and an alcohol becomes less vigorous the longer the ...
2
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1answer
231 views

How to create 1-100 ppm ethanol gas?

I am trying to use TGS 2602 sensor of air contaminants. I would like to test if my circuit is working as intended. For that purpose I need to generate fumes of one of the gases the can be detected by ...

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