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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Taking volume contraction into account when mixing water with ethanol

To calculate the amount of purified water and the amount of ethanol (96% Vol.) which is needed for a desired/variable amount of a mixture - given a desired/variable percentage of ethanol - I use the ...
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What is the OH in alcohol?

What is the $\ce{OH}$ functional group in alcohol (ethanol)? My teacher told me it isn't the same as the $\ce{OH-}$ ion or hydroxide. But it does donate one electron to the respective carbon chain and ...
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1answer
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Mechanism for oxidation of primary alcohols to carboxylic acids

My teacher told me that the following is the mechanism for oxidation of primary alcohols to carboxylic acids: I've searched in books and online and didn't find a similar mechanism. For example, in ...
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215 views

Mechanism of ring formation of an epoxide under acidic aqueous conditions

I am trying to figure out the mechanism of this reaction: I think the $\ce{H+}$ will first attack the oxygen of the epoxide and another $\ce{OH-}$ will be added to the most substituted carbocation, ...
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1answer
297 views

Are gem-diols on alkenes stable?

Geminal diols are unstable, except for a few exceptions like chloral hydrate. I wish to ask if a gem-diol alkene is also stable. Their structure: suggests to me that the intramolecular hydrogen bond ...
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1answer
326 views

Hydroboration on Limonene

I saw that the hydroboration of Limonene (1-Methyl-4-(1-methylethenyl)-cyclohexene) does only happen on the methylethenyl group. Up to now, I wasn't able however to find out why. Generally speaking, a ...
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1answer
3k views

For what reasons, is isopropyl alcohol widely used as a cleaning solvent?

I have worked in electronics and aeronautics industry 30 years ago, and I have always wondered, what were the specific properties of isopropyl alcohol, which make it used instead of other alcohols ...
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1answer
5k 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 ...
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2answers
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How to convert ethanol to benzoic acid? [closed]

I have tried this method: Can anyone suggest me a shorter route? Criteria: Benzene has to be produced, it is not available. Edit : I don't understand why the question has been put on hold. They ...
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1answer
434 views

Naming of ester alkoxide

I'm trying to name the following compound: I believe the carboxyl group has priority and should make up the parent name. I'm not sure how to name the alcohol derivative portion. My first thought is: ...
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1answer
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Why are 1,3-diols protected with aldehydes but 1,2-diols are protected with ketones?

1,3 diols are usually reacted with benzaldehyde when protection of the OH groups is desirable, but acetone is used when the relation between the hydroxyl groups is 1,2. Why is it so?
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Synthesizing 2-methyl-2-butanol

I have recently been trying to come up with a method to synthesize 2-methyl-2-butanol or tert-amyl alcohol. I wish to avoid complex/expensive steps since as a home chemist/student, I don't have access ...
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1answer
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How do I arrive at the α-trimethylsilyloxy ketone from an unmodified ketone using TMSCl, triethylamine and mCPBA?

I'm confused about what is going on here. I gather that step 1 is typically supposed to protect an OH group, but there isn't any in the starting material.
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1answer
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Solubility order for alcohols [closed]

Order for solubility of isomeric alcohols in a book was given as: Primary alcohol >Secondary alcohol >Tertiary alcohol After this I found a question as : 1) Which is more soluble in water? (a) 3-...
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1answer
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Protonation of a compound having alcohol and ethereal linkage

I approached the problem this way: The ethereal oxygen gets protonated(due to greater + I , the electron density on it is higher, hence it is more likely to behave as a lewis base). Consequently the ...
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1answer
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By which mechanism would azide react with alcohols or alkyl halides?

$\ce{NaN3}$ produces $\ce{N3-}$ ions. So the reaction with an alkyl halide will either be $\mathrm{S_N1}$ or $\mathrm{S_N2}$. After some reading, I found that $\ce{N3-}$ is a good nucleophile. Hence ...
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1answer
357 views

Preparation of 6-bromo-1-hexanol

I am refluxing $\ce{HBr}$ with 1,6-hexanediol for 16 hours at $80\ ^\circ\mathrm{C}$ in toluene. How can I be sure that more than $90\,\%$ of the product is brominated only at one terminal? If the ...
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1answer
123 views

Fermentation in beer (reaction schemes)?

I've been struggling with this for a while, and I can't seem to solve the problem. Alcohol is made in the fermentation process in beer: Sugars formed during mashing (maltose and maltotriose) will ...
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134 views

False positive in lucas test for primary alcohol due to formation of tertiary carbocation by rearrangement?

From Wikipedia: The Lucas test in alcohols is a test to differentiate between primary, secondary, and tertiary alcohols. It is based on the differences in reactivity of the three classes of ...
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1answer
667 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 ...
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527 views

Why doesn't a halide anion react with primary or secondary alcohols using SN2?

In the tenth edition of Organic Chemistry by Solomons and Fryhle, section 6.18A of the "Ionic Reactions" chapter, in the last paragraph, they have mentioned that: Use of a weakly basic anion such ...
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1answer
72 views

Reduction of an Allylic Enoate to afford allylic alcohol in presence of Benzyl Acetal Groups

I have a question that requires finding a reagent for the reduction of an enoate to the corresponding allylic alcohol. Preferably done in one step too with an acid workup at the end too. What types ...
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1answer
105 views

Chemical shifts of OH protons

The chemical shift of a proton is an indication of the amount of shielding it receives from the electron density on it or other magnetic anisotropy effects present in the molecule. For the protons of ...
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2answers
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What is an aromatic alcohol?

The following question was given in NCERT Exemplar Problems (Class XII): According to Wikipedia: In organic chemistry, the aromatic alcohols or aryl-alcohols are a class of chemical compounds ...
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976 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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How to clean glassware containing pesticide solutions

I have pesticide (dimethoate) dissolved in methanol in volumetric flasks and graduated cylinders. How do I clean this glassware properly before moving on to the next dilution of a different pesticide.
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1answer
272 views

About purifying ethanol - What type of ethanol?

I'm reading this book, trying to learn some basics of chemistry. One of the experiments is about purifying ethanol. Now, I have some difficulties in deciding what kind of ethanol solution I should ...
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1answer
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Dehydration of secondary alcohol via E1 mechanism

Write the mechanism for this reaction: I am trying to do a dehydration of an alcohol using the reagents sulfuric acid and acetic acid. I don't know how I am supposed to use the acetic acid, ...
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1answer
354 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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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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534 views

What is the mechanism for the oxidation of a lactol to a lactone?

Recently, I came to know that lactols can be converted to lactones but I wasn't able to find the suitable reagent and the reaction mechanism. Can someone elaborate the same?
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1answer
987 views

Simple distillation & azeotropes

In my organic chemistry lab, we recently had an experiment where we were given a mixture of 50:50 ethanol & ethylene glycol. We were supposed to perform a simple distillation to calculate the ...
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1answer
605 views

Why don't periodic acids convert alkenes to 1,2 diols?

Periodic acids cleave 1,2 diols by forming an periodate ester as an intermediate. Osmium tetroxide also forms an osmate ester with alkenes and yields syn diols after a hydrolysis step. Given that ...
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160 views

Why mixing water with ethanol produces heat energy? [closed]

Sorry if I'm asking something stupid but I'm trying to understand where this energy gets from. As far as I could find, it is not a reaction as both chemicals left unchanged, so it might have something ...
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417 views

Number of intermediates and transition states in hydration of given alkene

What is the number of transition states and intermediates formed in the following reaction? My thought: First the alkene extracts $\ce {H^+}$ from the acid to form a carbocation. This step ...
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0answers
589 views

Can oxidation of ethanol by copper(II) oxide yield copper(I) oxide as one of the products?

We know that ethanol is oxidised by copper(II) oxide to an aldehyde. Copper is reduced from $\ce{Cu^2+}$ to $\ce{Cu}$. Can this reaction, with some specific condition, yield $\ce{Cu2O}$ instead? That ...
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3answers
7k views

How to test for methanol?

I wanted to make some ethanol from baker's yeast and I used sucrose. I've made it and put it in a glass jar. I left it on a warm place (near the radiator) until the yeast died and after they died I ...
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3answers
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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 ...
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1answer
144 views

Is Pinacol rearrangement the source for the ring expansion?

I have no idea what's happening as in the product (the answer is (a)) there is a new ring being formed on the left benzene. But as I studied after $\ce{H2O}$ leaves, a carbocation is then formed on ...
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4answers
152 views

Chlorinating specifically one carbon on a symmetrical alcohol

The final target molecule is 1-chloro-2-amino propane. The amination step would be simple via reductive amination of 1-chloro-iso-propanone. Obtaining 1-chloro-iso-propanone would be from ...
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2answers
368 views

Is HDPE affected by long term exposure to methanol?

For at least several years I'be been storing various chloride solutions with methanol as a solute in Nalgene containers, which I believe are made from high density polyethylene (HDP). But recently ...
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1answer
121 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 ...
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What is the mechanism for the hydrolysis of the boron-alkoxide complex in NaBH4 reduction?

According to this question, the stoichiometry of the reduction of a ketone is such that sodium borohydride can reduce up to 4 ketones by forming a boron-alkoxide complex. The next step would involve ...
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1answer
10k views

Why do alcohols and ethers have approximately the same solubility in water but different boiling points?

In Morrison & Boyd, I found this question: Butan-1-ol (b.p. $118~\mathrm{^\circ C}$) has a much higher boiling point than its isomer diethyl ether (b.p. $35~\mathrm{^\circ C}$), yet both ...
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1answer
175 views

Does sulfuric acid formed in a previous step dehydrate a secondary alcohol?

In the following reaction won't the sulphuric acid dehydrate the secondary alcohol after it's formed?
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677 views

What is a good way for a laymen to purify alcohol to near 200 proof?

I'm making herbal and medicinal mushroom tinctures and extracts. Normally I'll use everclear but it isn't cheap and 95% alcohol. Also I don't know what that other 5% is. Is it just water? Is ...
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1answer
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Alcohol irregularities in Hydrogen NMR

We've started learning about NMR in my ochem class and my instructor told us that in Hydrogen NMR an alcohol can have a fairly wide range of possible values - usually from about 2 to 5. He said that ...
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1answer
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How to get the freeze point of mixed liquids?

I recently bought in Italy a bottle of "Alcool puro" which is in fact 95% Alcohol and 5 % Water. So alcohol has a freezing point of -114°C and water a freezing point of 0°C. How can I calculate then ...
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1answer
129 views

Mass Spectra: 1-pentanol vs 3-pentanol

In mass spectrometry, 1-pentanol can be observed to have no peak at $m/z = 59$, whilst 3-pentanol can be observed to have a peak at $m/z = 59$. Clearly the 3-pentanol peak at $m/z = 59$ is due to the ...
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1answer
299 views

What is the function of tosylchloride in the synthesis of an ether?

Considering the following reaction: Today my teacher explained this reaction as follows: The electron pair of $\ce{OH}$ (in the first compound) will "attack" the $\ce{S}$, making the $\ce{Cl}$ "jump ...

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