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
54 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
41 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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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 ...
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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 ...
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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
18 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 > ...
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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 ...
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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)? ...
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1answer
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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
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 ...
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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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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
34 views

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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0answers
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 $3^\circ$ ...
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0answers
53 views

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, ...
1
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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 ...
0
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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?
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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 ...
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?
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 ...
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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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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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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%....
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 ...
6
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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 ...
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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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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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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
26 views

Grignard alkoxide intermediate as starting material for ether or ester synthesis

I'm having a Grignard reaction between a ketone or aldehyde with RMgX in mind. The average workup uses water to hydrolize the intermediate alkoxide. But could this intermediate be used without ...
1
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1answer
86 views

Conversion of methylcyclopentanol to cyclopentanone

How to convert methylcyclopentanol to cyclopentanone? I tried eliminating the alcohol group as $\ce{H2O},$ but that gives Saytzeff product. If only I can get the Hofmann product (methylene ...
5
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0answers
88 views

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 ...
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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1answer
45 views

Comparing between cleavage of ethers

We have to find out which ether would undergo cleavage faster. My Attempt IV. I couldn't figure out, so i carried out simple SN1 cleavage. Since +M effect of OH > OCH3 1st reactant seemed right ...
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0answers
29 views

Under what conditions can epoxide undergo oxidation by HIO4

Question Doubt Can epoxide react with HIO4. I have seen that in same cases they do. But in this given question they don't. If they do react , then how and what will be the products?Please help
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20 views

Problem detection in reaction procedure

We all know that oxidation of secondary alcohols leads to ketones. So, with that logic, in order to form acetone $CH_3-CO-CH_3$ through oxidation, we need a secondary alcohol like isopropyl alcohol. ...
0
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1answer
28 views

Benzylation and acetylation of amines and alcohols

Question Attempt Since the nitrogen site is more nucleophilic it should react first. But still Oxygen can react and hence I believe A should be right. But the book says C. Where did I go wrong? ...
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1answer
238 views

2-Methylpropan-2-ol and Iodoform test

Can 2-methylpropan-2-ol be converted into methyl ketone the action of $\ce{I2}$ in the presence of alkali base and thus give iodoform test? Answer given to this question is that it can't give ...
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1answer
105 views

Rubbing alcohol gets warm after diluting with water

I've just diluted a 95% rubbing alcohol bottle with water to bring it down to 70%. However, the bottle got noticeably warmer after I did so. I've searched online and I couldn't find any exothermic ...
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1answer
2k views

What type of plastic (PET, HDPE etc.) is appropriate to store alcohol based hand sanitizer? [closed]

I’ve been tasked with distributing hand sanitizer to public safety staff from a bulk supply in gallon jugs. I need a portable squeeze bottle, but I’m having trouble determining what type of plastic (...
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2answers
252 views

How many hydrogen bonds can methanol make?

I believe that it can form 2 hydrogen bonds, one with oxygen and the other with hydrogen but a classmate said that oxygen can form 2 hydrogen bonds? Is this true? I can't find anything on google to ...
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0answers
66 views

Is there an exothermic reaction when washing hands with water and hand sanitiser?

I accidentally washed my hands with water (cold/lukewarm) and hand sanitiser alcohol (room temperature) instead of soap. I felt like my hands have gotten warmer when I applied it. Only using alcohol ...
5
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1answer
52 views

Disubstituted cyclic alcohols - looking for IUPAC rule

Given a simple cyclic alcohol: We can name it cyclopentanol and using cyclopentan-1-ol wouldn't be correct. When more than one ...
7
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1answer
305 views

Why does a proton prefer to attack a double bond instead of protonating an alcohol in a reaction of unsaturated alcohol with sulphuric acid?

A solved problem in Organic Chemistry by Solomons, Fryhle and Snyder asked to write the mechanism for the following transformation in the presence of sulphuric acid ($\ce{H2SO4}$): The mechanism ...

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