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.

Filter by
Sorted by
Tagged with
0
votes
2answers
56 views

Confusion regarding mechanism of dehydration of alcohols [closed]

1)Today I came across a problem which asks to find the order of dehydration of 2-hydroxycyclohexanone(1), 3-hydroxycyclohexanone(2),4-hydroxycyclohexanone(3). The answer is 2>3>1 But I thought ...
1
vote
2answers
43 views

Intramolecular Cannizzaro reaction product

I came across the following question : My reasoning was as follows : It can't be option (c) because there is no chance of losing a carbon during Cannizzaro's reaction It can't be option (b) because ...
0
votes
0answers
26 views

Alcohols are a homologous series. However, you can get aromatic, aliphatic and alicyclic alcohols. Are there separate homologous series for each type? [closed]

In my textbook, it says that alcohols are one homologous series with the hydroxyl (-OH) functional group. However, there are aromatic, aliphatic and alicyclic alcohols. In one homologous series, can ...
0
votes
1answer
20 views

Methanol-water mix freezing points - clarify contradictory online data > 60% w/w?

Extending an exploration of windshield washer-fluid choices to freezing points of methanol-water mixes, all web-sources located agreed to within a couple of degrees from 0-60% w/w, yet above this ...
2
votes
1answer
81 views
+50

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 ...
0
votes
0answers
44 views

Is my bottle of “RooR”-brand glass cleaning liquid pure isopropyl alcohol or something else?

I have this exact bottle: https://www.grasscity.eu/media/catalog/product/cache/2b55fa971a29a7844993ad77b24950ac/i/m/img_3633_1_1.jpg I originally purchased it to clean my vaporizer (I've since stopped ...
4
votes
1answer
52 views

On the molybdenum(III) oxide-catalysed oxidation of alkanes to carbonyls

The following reaction is specified in my notes; $$\ce{CH4 ->[Mo2O3, \Delta]HCHO}$$ The intermediate steps involve the dehydration of an alcohol to yield the final product. Wouldn't this only work ...
-3
votes
0answers
32 views

Manganese(IV) oxide oxidation of carbocations [closed]

As I understand it, $\ce{MnO2}$ selectively oxidises benzylic and allylic alcohols to carbonyls. But this also works for making alcohols out of carbocations, apparently. I found the following ...
2
votes
1answer
64 views

Periodic acid oxidation of carbonyls?

The following reaction seem to be valid; $\ce{CH2OH-CHOH-CH2OH ->[HIO4]CH2O + HCOOH + CH2O + 2H2O}$ Apparently, there are similar reactions by 2,3-dihydroxypropanal, and also by the straight chain ...
5
votes
1answer
124 views

Why there is a color fading ( to colorless) when Cerium Ammonium Nitrate (CAN) is mixed with ethanol or butanol? [duplicate]

I have mixed CAN in butanol and also ethanol (separately), the solution became dark red immediately but after a couple of minutes the color totally faded and turned into a transparent solution, I am ...
1
vote
1answer
43 views

On the relative ease of E2 dehydration

Concerning alcohol dehydration, I get that it's E1 in secondary and tertiary alcohols, that it's E2 in primary alcohols, and also why E1 reaction is easier for tertiary alcohols as compared to ...
0
votes
0answers
30 views

Is it possible to distinguish between cyclohexanol and cyclohex-2-en-1-ol?

Primary, secondary and tertiary alcohols can easily be distinguished by using reagent tests such as: The Triiodomethane test for R-CH(CH3)OH alcohols Lucas' reagent to distinguish between the 3 ...
2
votes
1answer
154 views

IUPAC name of cyclopentanol derivative

Is the name of the following compound 3-(ethenyl)-5-(prop-1-enyl)-2-(prop-1-ynyl)-4-(prop-2-enyl)cyclopent-2-en-ol? The problem I am facing is that how do I arrange 5-(prop-1-enyl), 2-(prop-1-enyl) ...
0
votes
0answers
49 views

Possibility of removing two water molecules from glycerol

Not a chemist, but from a chemical formula perspective, how hard would it be to create acetone by acidifying glycerol? $$\ce{C3H8O3 + 2 H+ <=> C3H6O + 2 H2O}$$ Has anyone ever heard of this ...
1
vote
0answers
38 views

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 ...
1
vote
0answers
25 views

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 ...
0
votes
0answers
38 views

Reaction between phosphorus(III) bromide and alcohol

Alcohol acts as a nucleophile in a reaction with $\ce{PBr3}.$ It attacks the $\ce{PBr3}$ leaving $\ce{Br-}$ behind. The alcohol forms a bond with the $\ce{PBr2+}.$ How the oxygen having three bonds ...
3
votes
1answer
104 views

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-...
2
votes
0answers
42 views

Show the mechanism of the Pinacol-Pinacolone Rearrangement reaction [duplicate]

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 will it give such a product. I cant see any way to make ...
2
votes
0answers
21 views

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 ...
0
votes
1answer
54 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. ...
0
votes
3answers
113 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'...
0
votes
0answers
44 views

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 ...
6
votes
1answer
433 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. ...
3
votes
1answer
122 views

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 ...
1
vote
2answers
125 views

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?
1
vote
0answers
249 views

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 ...
2
votes
0answers
45 views

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....
2
votes
1answer
149 views

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 ...
0
votes
1answer
220 views

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. ...
1
vote
2answers
79 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 ...
3
votes
0answers
125 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 ...
1
vote
0answers
35 views

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. ...
1
vote
3answers
854 views

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?...
0
votes
0answers
87 views

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 ...
0
votes
1answer
82 views

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 ...
2
votes
0answers
40 views

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 ...
0
votes
1answer
140 views

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'...
0
votes
0answers
21 views

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 ...
1
vote
0answers
29 views

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 ...
2
votes
1answer
146 views

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 ...
0
votes
1answer
86 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 ...
0
votes
0answers
20 views

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 ...
-1
votes
1answer
39 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 ...
1
vote
0answers
49 views

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 ...
0
votes
0answers
48 views

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 > ...
0
votes
1answer
479 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 ...
0
votes
0answers
812 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 ...
10
votes
2answers
1k views

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)? ...
-1
votes
1answer
29 views

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 ...

1
2 3 4 5
10