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.
456
questions
-3
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0answers
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?
0
votes
0answers
16 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
0answers
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 ...
-3
votes
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 ...
0
votes
0answers
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 ...
10
votes
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)?
...
-1
votes
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
votes
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 ...
-1
votes
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 ...
-2
votes
0answers
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?
0
votes
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 $\mathrm{S_N2}$ ...
0
votes
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 ...
0
votes
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.
...
0
votes
0answers
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 $3^\circ$ ...
1
vote
0answers
46 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
vote
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 ...
0
votes
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?
0
votes
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 ...
4
votes
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?
4
votes
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
votes
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 ...
1
vote
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.
2
votes
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 ...
0
votes
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%....
2
votes
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 ...
-4
votes
2answers
70 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
votes
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 ...
4
votes
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 ...
-1
votes
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.
0
votes
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 ...
1
vote
0answers
40 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
votes
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 ...
2
votes
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
vote
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 ...
5
votes
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
votes
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.
-2
votes
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 ...
0
votes
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
0
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0answers
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
votes
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? ...
0
votes
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 ...
0
votes
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 ...
-2
votes
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 (...
1
vote
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 ...
0
votes
0answers
58 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
votes
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 ...
7
votes
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 ...
1
vote
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
votes
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 ...
14
votes
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 ...
