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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27 views

Are Cross Products Possible in the Claisen Rearrangement? [closed]

I have seen a question of FRIES Rearrangement in which Cross products are possible, Is it possible for Claisen Rearrangement too?
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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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27 views

Safe sprayable fast-drying liquid for mould release agent [closed]

I am looking for a safe sprayable (will be sprayed as a fine mist) liquid that I can use as a base for a mould release. The mould release is simply melted paraffin wax suspended in the liquid which is ...
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1answer
47 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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42 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
903 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
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 ...
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3answers
262 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
48 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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26 views

Finding product when 3-ethyl-3-methylhexan-1-ol is dehydrated [closed]

Find the major product when 3-ethyl-3-methylhexan-1-ol is treated with concentrated sulphuric acid. I think it can be 3-ethyl-4-methyl-hex-3-ene. What should be the correct answer?
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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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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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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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32 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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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
93 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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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
60 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 ...
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1answer
145 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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2answers
255 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
912 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
44 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.
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2answers
138 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
32 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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1answer
33 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
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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 ...
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1answer
121 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 ...
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2answers
417 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
67 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
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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 ...
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1answer
101 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 ...
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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 ...
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1answer
78 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 ...
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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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2answers
336 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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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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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. ...
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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
205 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
64 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
183 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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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 ...
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1answer
51 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 ...
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1answer
246 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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0answers
53 views

Adding an essential oil to WHO Handrub Formulation [closed]

I'm not a chemist, so I prefer to ask this question to some people, who definitely have knowledge in that area. WHO Handrub Formulation is available here. Ingridients: Ethanol 96%, Hydrogen peroxide ...
2
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1answer
130 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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3answers
6k views

When I burn isopropyl alcohol (IPA), it burns orange. But when I burn ethyl alcohol, it burns totally blue. Why is this?

I burned them in a small aluminium tray. While IPA is burning orange, it produced the smell of soot, but while ethanol is burning blue there isn't any smell. Also, ethanol made the tray really cold ...

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