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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2
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1answer
53 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 ...
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0answers
20 views

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
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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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2answers
441 views

Identification of the organic compound

An organic compound A $(\ce{C10H14O})$ exhibits following characteristics. A) It reacts with metallic sodium to give a colorless odorless gas. B) It is oxidized by $\ce{KMnO4}$ to benzoic acid. C) It ...
10
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2answers
655 views

Can a six member ring expand to achieve octet completion to stabilize a carbocation?

(Probably unnecessary background: I came up with this carbocation while predicting the major product of $\ce{NaNO2/HCl}$ with 1-(methylamine)cyclohexan-1-ol) Will the following carbocation ...
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0answers
17 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 ...
2
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1answer
350 views

Is propanol 1-2 diol 178 the same as propylene glycol?

I clean vinyl records in an ultrasonic vinyl record cleaning machine the manual states it uses propanol 1-2 diol 178 as a surfactant. I think this is the same chemical as propylene glycol. Is it?
3
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1answer
386 views

Why is ethanol distilled off before adding water in the first step of a malonic synthesis?

I am doing a malonic synthesis shown below, and I wonder why I should distill ethanol off before adding water in the first step of the reaction (First I add absolute ethanol and solid sodium).
-1
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1answer
33 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 ...
5
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2answers
2k views

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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0answers
43 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 ...
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0answers
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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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1answer
53 views

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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2answers
949 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
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3answers
22k views

What is reaction between isopropyl alcohol and acetone?

What would be the probable reaction between acetone, $\ce{(CH3)2CO}$, and isopropyl alcohol, $\ce{CH3CHOHCH3}$, at room temperature without any catalyst in different concentrations?
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1answer
54 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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0answers
46 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 ...
2
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1answer
77 views

Which functional group gets reduced first?

The following is a reduction reaction. In the reduction of 2 to 3, keto group undergoes reduction by nucleophillic addition. Ester could undergo nucleophillic acyl substitution to give an aldo group, ...
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1answer
24 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 ...
3
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3answers
279 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
50 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 ...
5
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3answers
5k views

Solubility of methanol and ethanol in water

Which substance is the most soluble in water? $\ce{CH3OH}$ $\ce{CH4}$ $\ce{C2H6}$ $\ce{C2H5OH}$ I wasn't able to decide between 1 and 4, as both have hydroxides, but the answer is 1. ...
1
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1answer
46 views

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.
2
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1answer
159 views

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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0answers
20 views

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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0answers
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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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1answer
33 views

Why am I getting higher conversion values of isopropanol dehydration over a zeolite catalyst then n-propanol dehydration?

The two process are run separetly but under the same condition, same activation of the catalyst, same reaction temperature, same flow. The initial conversion of n-propanol is ~50% and isopropanol ~70%....
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3answers
10k 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 ...
7
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2answers
352 views

Do amines or alcohols have stronger intermolecular hydrogen bonds?

Which has stronger hydrogen bonding, $\ce{CH3OH}$ or $\ce{CH3NH2}$ I think it comes down to which has more dominance; number of hydrogens, number of lone pairs, or electronegativity.
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35 views

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 $3^\circ$ ...
4
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1answer
149 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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1answer
96 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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0answers
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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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1answer
77 views

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?
2
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2answers
143 views

Rate of dehydration of alcohols having keto group

The following question was asked in IITJEE-Screening 2000, Which of the following will be most readily dehydrated in acidic conditions? I thought that the answer would simply be (c), as its ...
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2answers
61 views

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 ...
9
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5answers
29k views

Testing isopropyl alcohol purity

I'm curious how to test purity of isopropyl alcohol? I simply got very curious today. I bought rubbing alcohol and it doesn't say what's the purity anywhere. It could be 70%, but it could also be 90%, ...
4
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2answers
261 views

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 ...
5
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2answers
917 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 ...
5
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1answer
11k views

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 ...
2
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1answer
37 views

Plasticisers and other impurities from polyethylene laboratory bottles?

Does polyethylene (PE), widely used for wash/squirt bottles in labs, contain soluble compounds such as plasticizers that can accumulate in organic solvents (e.g. alcohols, acetone) after prolonged ...
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2answers
73 views

What are the differences and similarities of Sugar Alcohol and the Alcohol in Alcoholic Drinks? [closed]

Question part 1: In particular of Sugar Alcohols, I ask about Sorbitol. I am a 100% strict teetotaler. I do not care if a small dose will not intoxicate me, I am absolutely anti-alcoholic. Recently I ...
4
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1answer
130 views

Rate of dehydration for butan-2-ol and butane-2,3-diol

A question taken from a test series (Vibrant, India): Amongst butan-2-ol and butane-2,3-diol, which has higher rate of dehydration? The carbocation formed in butane-2,3-diol is more stable as it ...
0
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1answer
74 views

Why HCl is used in Lucas test?

In Lucas test $\ce{HCl}$ is used for acid-base reaction between $\ce{Zn(OH)Cl}$ to give $\ce{ZnCl2}$ and $\ce{H2O}$ which is kind of good because $\ce{ZnCl2}$ is formed again and used in first step ...
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1answer
35 views

What does the alcohol functional group (specifically oxygen) have to do that causes an alcohol to have a lower energy content than an alkane? [closed]

My textbook said that the carbon is "partially oxidised" (don't really know what that means) and I just wanted to confirm.
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0answers
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Oxidation of diols to dialdehydes

How could 1,4-butanediol be converted to 1,4-butandial (succinic aldehyde)? I thought of simple oxidation with $\ce{CuO}$ but apparently it yields gamma-butyrolactone according to erowid and this ...
2
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3answers
22k views

Can 99% isopropyl alcohol be stored in a clear container?

I'm planning to get hold of some 99% isopropyl alcohol (aka rubbing alcohol) for the purpose of cleaning electronics, and am going to transfer it from the plastic bottle it comes in to a smaller, ...
1
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0answers
47 views

Reaction of multiple diols with sulphuric acid [closed]

Find the total number of possible products I can think of atleast three reactions that will take place in the acidic medium: Pinacol-Pinacolone rearrangement Intermolecular dehydration (leading to ...
2
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1answer
133 views

Why does H+ attack alkene first in this reaction?

The reaction is: Why is the double bond attacked here even though it is in conjugation with the lone pairs of O thereby making it harder to extract. Also,don't the 2 lone pairs on OH have more ...
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 ...

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