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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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 ...
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1answer
49 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
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1answer
33 views
IUPAC name of iso butyl alcohol [closed]
In my school book there was a question to give the IUPAC name of iso butyl alcohol
I think the answer should be
2-methyl propanol
but in my book it is written
butan-2-ol
which is correct?
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0answers
20 views
What chemical compound(s) contribute to the signature odor in hand sanitizer? [closed]
We are a trio of senior high-school students who have a personal project to find out what exactly causes the odors in alcohol-based hand sanitizer. Our goal is to try to create an odorless hand ...
1
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0answers
29 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 ...
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1answer
115 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'...
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0answers
19 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 ...
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0answers
28 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
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1answer
61 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
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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 ...
0
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1answer
49 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
19 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
34 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
44 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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20 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
59 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
76 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
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2answers
951 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
25 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
288 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
52 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 ...
0
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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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39 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
61 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
101 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
63 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
153 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?
6
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2answers
274 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
918 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
155 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
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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
39 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
80 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
136 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
449 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.
0
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1answer
103 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
56 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
167 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 ...
3
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1answer
46 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
102 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
90 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
364 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 ...
0
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0answers
32 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. ...
