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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Mysterious violet-purple compound in "Gerber Method" & "Banana oil synthesis"
During the determination of fat in milk (Gerber method), in a milk butyrometer are mixed milk + $\ce{H2SO4}$ 90% w/w + isoamyl alcohol (isopentyl alcohol) and heating.
The acidic mixture separates ...
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Why isn't PBr3 used to halogenate tertiary alcohols?
I've been looking into activation of alcohols for nucleophilic substitution, and I've come across a series of reactions that differentiate between primary, secondary and tertiary alcohols. I've seen ...
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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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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 involves ...
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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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Reactivity of different alcohols with NaNH2 and CH3I
Identify the final product (B) in the following reaction:
I'm not sure how $\ce{NaNH2}$ and $\ce{CH3I}$ will react with the different types of alcohol present here. According to my solution,ether was ...
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How to decide the correct numbering of aminocyclohexenol?
I'm self studying for a university admission exam. So I'm relying fully on online sources to study, but I often get confused because of differing methods. This is one such case:
According to this ...
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Boiling point of pentanol isomers
Arrange the following alchohols and alkanes in increasing order of boiling point:
3-pentanol, n-pentane, 2,2-dimethylpropanol, n-pentanol
I understand that n-pentane would have the lowest boiling ...
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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 (...
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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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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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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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Ethyl acetate produces red colour on ceric ammonium nitrate test
When I did CAN test on ethyl acetate red colour was seen. I thought water may get added with Ethyl acetate to produce
this compound which in turn gave red coloration but carbon should not make three ...
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Major product of isomerization reaction
I am trying to come up with a logical mechanism for the following transformation, where 2-methylenecyclobutan-1-ol is converted to cyclopentanone under acidic conditions:
What I have tried to do was ...
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How to make a placebo drink taste convincing?
I'm trying to make a placebo alcoholic drink - something strong (cognac, whiskey or vodka). Is it possible to make a drink containing absolutely no alcohol taste like it's got 30 or 40% alcohol? What ...
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How can I purify ethanol from formic / boric / salicylic acid?
I need some ethanol pure and strong enough for technical purposes (fuel, solvent, cleaning agent, dissolving rosin for soldering flux, etc.). Food quality is not required though, denaturated one is ...
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Catering grade electrolysis of alcohol
Would the electrolysis of alcohol, specifically spirits, result in a potable end product? I'm looking for some novel cocktail ingredients.
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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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Intuition of the oxidation of alcohols?
I understand that primary alcohols oxidise to aldehydes and then to carboxylic acids, and secondary alcohols oxidise to ketones, while tertiary alcohols don't oxidise at all. However, I am struggling ...
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Removing DCC and its by-product from Steglich Esterfication
In my small research, I want to synthesize 3 alkyl gallates (ethyl gallate, butyl gallate, and hexyl gallate), and here's my overall reaction using Steglich esterification):
However, from reading ...
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Creation of a Solution of Liquid Latex + Sodium Caseinate with Polyvinyl Alcohol
I am going to be experimenting with creating different types of liquid latex formulations, primarily for the purposes of increasing shear strength and tear resistance, as well as just general ...
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Predict the products of organic reaction sequence
This is a reaction sequence involving alcohols, phenols, halides, alkenes ,alkanes etc , and the task is to identify all the compounds A to E
The few things I was able to identify :
The compound C ...
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Protecting Thiol group in presence of alcohol
What protecting group can I use that will protect the thiol in the presence of an alcohol? Is there a set of conditions, or a group that I can use that is selective to the thiol over the alcohol?
I am ...
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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 ...
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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 ...
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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 ...
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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
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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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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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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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1,5-Pentanediol MS
I'm having troubles assigning the signals m/z = 41 and 56 of the compound 1,5 pentanediol. I tried the basic fragmentations (McLafferty, loss of OH radical, etc.) but I can't figure the structure of ...
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Addition of NaBH4 and LiAlH4
NaBH4 and LiAlH4 will be a source for the hydride ion and reaction will begin with addition of hydride by displacing the carbonyl group.
But I am not sure will it attack both the carbonyl or only one....
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PF3 as a source of fluoride for substitution in alcohols
It is known that $\ce{PX3 (X= Cl, Br, I)}$ and $\ce{PX5 (X= Cl, Br)}$ are used to make halogen derivatives of hydrocarbons from alcohols. My question is why there's no information about using $\ce{PF3}...
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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 ...
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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 $\...
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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 ...
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What determines whether iodination or reduction will occur?
Alkyl Iodides are formed by reaction of alcohols with iodine and red phosphorus. I already am well aware that this forms $\ce{PI3}$ in situ, which acts similarly to $\ce{PBr3}$ and allows alkyl ...
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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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Can I make an alcohol-based stain from a pigment with an alkaline extraction process?
I'm in a situation where I don't really even know enough to know if what I want makes sense or has the kinds of problems that I think it might have, but here's the situation:
I would like to make a ...
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What is the rate of hydration in the following compounds
I came across a question :
What is the order of rate of hydration in the following compounds:
My attempt to this question was checking the stability of carbocation. As III has a possibility of 3* ...
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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 ...
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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 > ...
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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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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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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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What fluid can I store metal filings in so they do not oxidize?
I am working on an art project that will involve storing filings of various metals (e.g., iron, copper, zinc) in a colorless fluid. I want to prevent the metals from oxidizing for several years, so ...
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Proton NMR of tert-amyl alcohol
I just started learning about proton NMR.
According to Molbase, the HNMR data for tert-amyl alcohol (2-methylbutan-1-ol) shows four kinds of protons at 0.9 ppm, 1.24 ppm, 1.44, and 3.65 ppm.
However, ...
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Water solubility comparison of stereoisomers of bicyclo [4.4.0] decane-3,4-diol
I think, (I) must be more soluble in water. It is due to trans configuration and thus, forming more effectively inter-molecular hydrogen bonds with water molecules.
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Solubility of alcohols in non-polar solvents
The solubility of an alcohol in a non-polar solvent (like hexane) increases with size of the alcohol, as the non-polar chain increases. However, as the chain keeps increasing, will the solubility ...
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Rate determining step in oxidation of alcohols using chromium-related compounds
I wanted to ask a question about the kinetics of an oxidation reaction using chromium reagents.
I was given a lecture today on the mechanism of alcohol oxidations using Chromate (VI) reagents:
My ...
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