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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Can ink manufacturing companies use isobutanol instead of n-butanol?

Will there be any harmful effect if isobutanol is used instead of n-butanol? Will there any major change in the final product?
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Relationship between self ignition and pressure for 91% isopropyl alcohol

We know that the self-ignition temperature for alcohol is about 750F/399C, but I can't find information on how that self-ignition temperature changes with changes to pressure (psi or bar). ...
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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-...
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Show the mechanism of the Pinacol-Pinacolon Rearrangement reaction

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 it will give such product. I cant see any way to make the ...
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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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Piperonal from piperinic acid

Is it possible to get piperonal if I do this? How much would this yield? chlorinate the double bonds in the piperinic acid Then convert the chlorine into alcohol Use periodic acid for oxidation ...
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1answer
36 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. ...
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3answers
79 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'...
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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 ...
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1answer
315 views

Major product in dehydration of alcohol

Consider the dehydration of the following molecule with conc. $\ce{H2SO4}$ at $443 \text K$: The possible products are: The first one is the Zaitsev product and the second one Hofmann product. ...
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Intermolecular forces of attraction between positional isomers of alcohols

This seemingly trivial question is as follows: Why is the boiling point of 1-butanol ($\ce {117.7 ^\circ C}$) higher than that of 2-butanol ($\ce {99 ^\circ C}$)? The only reason I can think of is ...
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When does Alcohol act as Solvent and as a Nucleophile?

I was recently solving problems related to Alcohol. and its solution is My doubt is why methanol act as a nucleophile here and when does alcohol acts as a nucleophile and as a Solvent?
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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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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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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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Is it safe to mix methylated spirits with isopropyl alcohol?

I have about 200ml of methylated spirits and 500ml of 100% isopropyl alcohol that I want to mix together in a plastic drink bottle. I will use it for fuel in an alcohol burning stove while camping. ...
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1answer
46 views

Is 6-ethenyl-4-(prop-2'-enyl) octa-6-en-3-ol a valid name?

I recently study organic chemistry and I read a book by Sana Jamshaid. I came across this compound and I cannot understand why it named 6-ethenyl-4-(prop-2'-enyl) octa-6-en-3-ol: I understand that ...
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92 views

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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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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Why hydrogen bonds are stronger than Van der Waals forces?

Why the hydrogen bonds are more intense than Van der Waals forces in the case where the molecules with the Van der Waals forces have a stronger dipolar moment than the molecules with the hydrogen bond?...
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Number of stereoisomers of pentane‐2,3,4‐triol [duplicate]

What will be the number of stereoisomers of $\ce{CH3CH(OH)CH(OH)CH(OH)CH3}?$ By formula $2^n - 1 + 2^n + 1/2$ for $n$ being the odd number of chiral centres, it's $6;$ four optically active and two ...
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Nomenclature question about diols

I'm struggling to understand why the following organic compound: is named systemically as 2-ethylhexane-1,3-diol (I think its common name is etohexadiol), if the longest carbon chain in the molecule ...
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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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What are the products of alkene oxymercuration with diols?

I was wondering what would be the product of the reaction of alkene with a diol (such as glycol) in alkoxymerucuration/demercuration, i.e. $\ce{(CF3CO2)2Hg/NaBH4}$? I tried to look online but I couldn'...
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Halogenation by Phosphorous tribromide vs using HBr

My textbook introduced PBr3 by stating that it leads to an inversion in stereochemistry since it always goes through an SN2 pathway, unlike using HBr. My question is that since Br- is a reasonably ...
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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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1answer
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Mechanism of acid-catalyzed Robinson annulation?

My professor posed my organic chemistry class a challenge problem for bonus points and I've been racking my brain over the last three days trying to work it out and I want to know if my solution is ...
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Existence of gem-diols [duplicate]

In the mechanism for Reimer-Tiemann's reaction, I was told that two alcohol substituents on the same carbon atom are unstable, and this is why salicylaldehyde is formed. In fact, this is not the first ...
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1answer
76 views

Selection of parent carbon chain for IUPAC naming [closed]

How to select the parent carbon chain for IUPAC naming of following compound? I think the red numbering is correct, but in the answer key, they have used the blue numbering. Which is correct? My ...
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Alcohol VS acrylic

I'm trying find out if it is possible to reverse, or correct the effects of hairline cracks in acrylic caused by isopropyl alcohol. They are very mild. I'm not sure where to look for an answer or who ...
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38 views

Synthesis cost of Fomepizole

Fomepizole is essential drug for methanol poisoning, I observed it cost too much like in 1000's of dollar for couple of ml. Is cost due to patents, or due to synthesis cost,structure of molecule looks ...
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Chemistry and Plants [closed]

We're going to conduct a study to make corn husk fiber into a paper. Soda Ash is always used to extract the fibers from the husks, First question is there any chemical we can use aside from soda ash ...
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rate of combustion of alcohols and hydrocarbons in relation to the number of carbons in the chain

I understand that the heat released when burning alcohols is greater as long as the number of carbons in the alcohol chain is increased (i.e the enthalpy of butanol is greater than propanol > ...
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222 views

Oxidation of alcohols by Ceric Ammonium Nitrate

I have realized that reaction with ceric ammonium nitrate essentially results in coordination of alcohol with $\ce{Ce(IV)}$ and my teacher referred that we should be able to proceed it to form ketone ...
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398 views

Mechanism of reaction of alcohol with NaBr + H2SO4

My teacher told that the mechanism for reaction of alcohol with $\ce{NaBr + H2SO4}$ follows SN1 when alcohol is 2°/3° and SN2 when it is primary or methanol. He told that the reactivity of alcohol ...
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What is the name origin of ester?

Ester is quite a random nomenclature for a compound derived from a parent acid and parent alcohol. Is there any reasoning behind using the word 'ester' to name such compound (for memorising purpose)? ...
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Any plastic for long term storage of Puriss. Ethanol?

I'm being offered to share some puriss Ethanol. Can I store it long term in any plastic container without the slightest contamination/reaction from the plastic? I have HDPE, PET, but I could buy ...
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3answers
305 views

Isomerization reaction involving carboxylic acid derivatives

I have tried searching for what type of organic reaction this is in my textbooks and ended up with nothing. Thus, I could not fully understand and refer to the mechanisms that the solution has ...
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1answer
70 views

Reduction of epoxide

Does $\ce{LiAlH4}$ and $\ce{NaBH4}$ reduce an isolated epoxide? I have two books where both are saying differently. One says it can and other says cannot. On searching the web there was no definite ...
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1answer
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Lucas test in the presence of EWG like -CN

Does the given compound give Lucas test? My teacher says due to the presence of a strong electron withdrawing group the carbocation formed is unstable. But I say if it undergoes $\mathrm{S_N2}$ ...
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How do I get the smell of Febreeze (uncomplexed cyclodextrin composition) out of my carpet?

Help! I sprayed my old carpet, which had gotten a little mildewy from some wet towels left on it, with Febreeze original scent. Now I can't get that horrible scent out! It might also be mixed with ...
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Reaction of a cyclic tertiary alcohol with chromic acid

We know that $\ce{H2CrO4}$ cannot oxidize tertiary alcohols. The mechanism is: Now the ${\alpha}$ carbon does not have any hydrogen to proceed to next step. Therefore, this reaction would not occur. ...
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Extent of multiple hydride shifts in a carbocation

Take this example: Multiple hydride shifts are possible only if in each step, the formed intermediate is more stable than the previous one. (1) to (2) converts $2^\circ$ carbocation to $3^\circ$ ...
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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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125 views

Acid catalysed dehydration of alcohol with a bicyclo group

Pathway 1: Rate determining step is the formation of carbocation. In this pathway, a conjugated tertiary carbocation is generated as an intermediate. Pathway 2: One of the resonance form of ...
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Acid catalysed dehydration of 5-methylidenecyclopent-2-en-1-ol [closed]

I think the following reaction is NOT possible. I could not find a mechanism for ring expansion. Is ring expansion possible in any way? Is the following mechanism correct?
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Dehydration of primary alcohol with a cyclobutadiene substituent [closed]

Note: Primary alcohol will follow E2 mechanism, therefore, removal of protonated water and proton (RDS) shall proceed in a single step in the above mechanism. My questions are: 1- According to ...
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1answer
194 views

Yield of possible products from acid catalysed hydration of an alkene with a phenyl group

Here, (d) may be the major product due to high temperature. My questions are: Will a kinetically favoured (minor) product (c) form? What shall be the order of yield of products?
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Formation of toluene from (cyclobutane-1,2,3-triyl)trimethanol using conc. sulphuric acid

In my book this reaction is given without any mechanism: I thought that simple dehydration reaction is going to take place with rearrangement of the carbocation but I have no idea as to how toluene ...
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2answers
941 views

What chemical properties of ethanol make it usable for drinks as compared to that of methanol? [closed]

Methanol ($\ce{CH3OH}$) and ethanol ($\ce{C2H5OH}$) both are the organic compounds having an alcoholic group. The alcoholic beverages (liquors and spirits) for human consumption (albeit injurious to ...

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