Questions tagged [organic-chemistry]

Use this tag for questions relating to organic molecules and their properties (structure of organic molecules, spectroscopic properties, reaction mechanisms, stereochemistry etc). DO NOT use this tag as the only tag in your question, as this tag by itself cannot appropriately classify your question. Always use this tag in addition to other more specific tags.

Filter by
Sorted by
Tagged with
5
votes
0answers
61 views

What makes this molecule achiral?

I don't understand why this molecule is achiral: I've circled what I think is the sole chiral center in red. I thought that any molecule with exactly one chiral center is chiral without exception. I ...
2
votes
1answer
53 views

Reactions which confirms the presence of cyclic structure of glucose [duplicate]

Are there any reactions that can be explained only on the basis of the cyclic structure of glucose rather than the open chain thus confirming its presence in the solution? Like a reaction that can ...
4
votes
1answer
140 views

Origin of the term “millamolecule”

I came across a term "millamolecule" to represent macrocycles with a molecular weight between 500 and 1,000 daltons. Google Scholar show several resources which use this term e.g., Google Scholar ...
1
vote
0answers
34 views

Source of highly nucleophilic iodide [closed]

What is be the best commercially available source of highly nucleophilic iodide in non-polar solvent? Solvents used are cyclohexane, benzene, chlorobenzene. I can get ahold of bromide quaternary ...
1
vote
1answer
36 views

5-methylhexa-1,3-diene reaction with HBr [closed]

What will be the major product of the reaction? I guess that rearrangement will take place and give 5-bromo-5-methylhex-2-ene as a product, but I'm completely not sure
0
votes
1answer
36 views

Recommendations for textbooks with correct and up-to-date information

I recently began studying chemistry, only to find out that, apparently, concepts such as “octet expansion” and Lewis structures are outdated and incorrect. And I don’t mean they’re approximations of ...
5
votes
1answer
124 views

Acid-catalysed isomerisation of phenyl epoxide to aldehyde

How does $\ce{H3O+}$ cause the formation of an aldehyde from the following epoxide? I thought that the epoxide would undergo opening to form a 1,2-diol, as illustrated below. Am I wrong?
1
vote
1answer
78 views

Why doesn't H₄CO₄ exist as a stable compound? [closed]

Why doesn't $\ce{H4CO4}$ exist as a relatively stable compound? Its heavier homologue $\ce{H4SiO4}$ seems to exist although it is unstable to some extent but new methods have been able to stabilise ...
1
vote
0answers
33 views

Oxidation of ascorbic acid (Vitamin C) [closed]

What would you suggest me to use for oxidation of vitamin C to dehydroascorbic acid instead of bromine water?
1
vote
0answers
37 views

Difference between liquid and solid stearic acid

I had some stearic acid in solid pellet format. It is slippy and in white color. I used this to make some experiments. I recently notice that some manufacturer can supply liquid stearic acid. I ...
1
vote
0answers
85 views

Does aniline react with FeBr₃?

I have read that aniline does not undergo Friedel–Crafts reaction because it complexes with Lewis acid $\ce{AlCl3}.$ Will it also react with $\ce{FeBr3}$ during bromination (to receive a 3-bromo ...
2
votes
3answers
150 views

I have a solution of citric acid, tartaric acid, water and glucose. How do I find the concentration of the citric acid present in the solution?

If I try to find the concentration of citric acid through back titration or reverse titration, the base I would use, like NaOH, would react with both acids to form sodium citrate and sodium tartrate, ...
-1
votes
1answer
45 views

Mechanism of the reaction of cyclohexanol and concentrated nitric acid to form adipic acid [closed]

If someone could please give me the hint to how the initial attack is carried out, it'd be a huge help.
3
votes
1answer
125 views

Is Pinacol rearrangement the source for the ring expansion?

I have no idea what's happening as in the product (the answer is (a)) there is a new ring being formed on the left benzene. But as I studied after $\ce{H2O}$ leaves, a carbocation is then formed on ...
3
votes
1answer
76 views

Why does phenolphthalein form in this reaction?

This reaction (http://orgsyn.org/demo.aspx?prep=CV1P0476) gives quinizarin as the major product in about 70% yield. However, when the same reaction is conducted with phenol insteas of p-chlorophenol, ...
4
votes
1answer
52 views

Reduction of an Allylic Enoate to afford allylic alcohol in presence of Benzyl Acetal Groups

I have a question that requires finding a reagent for the reduction of an enoate to the corresponding allylic alcohol. Preferably done in one step too with an acid workup at the end too. What types ...
3
votes
1answer
43 views

C−H bond length in organic compounds [duplicate]

I am reading Fundamental concepts of organic chemistry by Dr. Anju Srivastava (12/04/2007). It shows that carbon-hydrogen bond in ethane is 1.1 Å long, in ethene it's 1.08 Å, and in ethyne it's 1.06 ...
8
votes
2answers
311 views

What products do 4-nitrobenzaldehyde and 3-nitrobenzaldehyde give in a crossed Cannizzaro reaction and why?

What are the products of reaction of 4-nitrobenzaldehyde with 3-nitrobenzaldehyde in the presence of $\ce{NaOH}$ when they show Cannizzaro reaction? To my understanding, 4-nitrobenzaldehyde has more ...
1
vote
0answers
45 views

Synthesis of Aspirin

In my lab experiment for the synthesis of Aspirin we used hot water to quench the reaction. Why wouldn't we use cold water but hot water?
4
votes
2answers
60 views

Why does the nitrile carbon experience more shielding than a carbonyl carbon in CNMR?

In organic chemistry lecture, we were given a chart of approximate signal shift ranges for different carbon types in CNMR spectra. carbonyl carbons (C=O) have a range of about 155-210 ppm, but the ...
0
votes
2answers
54 views

Nomenclature of ester with cyclic substituents

I have to tell the name of the following compound The name is cyclopropylmethyl cyclobutanecarboxylate. All of it makes sense but I don't understand why the suffix carboxylate comes? Why are we ...
0
votes
1answer
38 views

The product of the reaction of chloroiodoalkane and cyanide ion in acetone

What would be the product of the following reaction $\ce{Cl-CH2-CH2-CH2-I + KCN} $ ($\pu{1mol}$ each) in acetone? I think the reaction should follow the second order nucleophilic substitution ...
3
votes
1answer
45 views

Why does the O atom of N-phenylnitrosamine donate its lone pair towards H+ when O is more electronegative than N?

Nitrogen has lone pair as well which it can donate towards the proton but instead we see the oxygen being protonated despite being more electronegative. Also, this is not like the next part where $\ce{...
6
votes
1answer
263 views

Large difference in boiling points of tetrafluoromethane and tetrachloromethane

Why is carbon tetrachloride $\ce{CCl4}$ is seen to posses liquid state (b.p. $\pu{76.72 °C}),$ whereas carbon tetrafluoride $\ce{CF4}$ is in gaseous state at room temperature (b.p. $\pu{−127.8 °C})?$
0
votes
1answer
73 views

What is the oxidation state of copper in Gilman's Reagent? [closed]

What is the oxidation state of copper in Gilman's reagent? In $\ce{R-Cu}$ bond the oxidation state is +1. Thus in $\ce{R-Cu-R}$ bond the oxidation state has to be +2. But if that so why positive $\ce{...
2
votes
1answer
32 views

Remove stain from synthetic leather

I have a valuable soccer ball. It is not real leather, but a synthetic leather. I used this cleaning agent to remove a few marks: https://www.amazon.co.uk/Motsenbockers-Lift-Off-Graffiti-Remover-...
1
vote
1answer
103 views

How many distinct dichlorination products can result when isobutane is subjected to free radical chlorination?

How many distinct dichlorination products can result when isobutane is subjected to free radical chlorination? I think that three distinct products may result namely a) 1,1-Dichloro-2-methylpropane b)...
0
votes
0answers
48 views

Reaction of alkyl halides with potassium cyanide

Its given in my book that alkyl halides react with alcoholic potassium cyanide to give alkyl cyanide through $\mathrm{S_N2}$ mechanism. But why do we need to use alcoholic $\ce{KCN}$ (potassium ...
0
votes
0answers
38 views

Preparation of compounds using acetoacetic ester synthesis

I've been given the following exercise in organic chemistry, and I'm at a complete loss. The text book doesn't cover the subject at all. I have some knowledge of melonic ester synthesis. As an ...
0
votes
0answers
25 views

What exactly is an 'activated' alcohol? Benzylic vs. Allylic vs. Aliphatic

I'm currently writing a report about the oxidations of various alcohols using different catalytic systems. In all papers it is stated that benzylic and allylic alcohols are "activated", while ...
0
votes
0answers
27 views

What factors affect the chemiluminesnence of a glow stick reaction?

I know that temperature affects the reaction rate of a glowstick, but are there any other factors? I was thinking the different color dye molecules would have an effect on the reaction rate, since ...
1
vote
0answers
33 views

How can we calculate the “degree” of conjugation?

So a conjugated system is a system of connected p orbitals or alternating single and multiple bonds. I know that conventionally, we count the number of adjacent parallel p orbitals or alternating ...
4
votes
2answers
304 views

Selective reduction of nitro group to amine, in benzene ring containing nitrile?

I would like to know if there is a possible route of synthesis that may reduce the shown compound A to the following product B. I would normally reduce a nitro to an amine using $\ce{Pd/C}$ and $\ce{...
0
votes
1answer
31 views

How will the degree of conjugation effect the light emitted? (glow stick reaction)

So regarding the chemiluminescence in a glow stick reaction, the glow is due to the unstable compound 1,2-dioxetanedione decomposing into carbon dioxide, releasing energy which is then absorbed by the ...
1
vote
0answers
28 views

which oxygen atom make intramolecular hydrogen bond in salicyclic acid?

When I googled about intramolecular hydrogen bonding in Salicylic acid, I found that there are two type of hydrogen bonding. Which one is more appropriate? And another question, if there ARE two ...
2
votes
1answer
32 views

How do Lewis acids interact with 1,4-diketones and amines to form an alkaloid?

The following double cyclization was used to generate the ring system of the lycoanitine alkaloids in 2005. Demonstrate your understanding of this C−C bond-forming process by providing a mechanistic ...
0
votes
0answers
14 views

Why homolytic fission of polar molecules is possible at higher temperature?

While studying alkanes I came across the nitration of alkanes using Nitric acid at very high temperature, which apparently follows "free radical" mechanisms, by formation of OH° °NO2 free radical ! ...
-1
votes
2answers
48 views

Why does a substance such as methane have 4 sp3 orbitals rather than 3 orbitals [closed]

I have been learning about SP3 hybridisation and slightly confused why it it results in 4 sp3 orbitals. My understanding is this... The S orbital is spherical and uniform whilst the p orbitals are ...
1
vote
0answers
35 views

Fischer Esterification of the Unsaturated 3-Butenoic Acid with Methyl Alcohol

I am attempting to perform a Fisher esterification of 3-butenoic acid (vinyl acetic acid). I believe that this should theoretically work and not disturb the unsaturated region of the molecule, but I'm ...
1
vote
0answers
37 views

Confused about identifying delocalized electron pairs in Isoniazid

I have to identify delocalized electron pairs in Isoniazid (pairs not shown in the image below): I know the nitrogen in the ring has a localized electron pair, since it already forms a pi bond. I'm ...
0
votes
0answers
21 views

Benzannulation of 18-crown-6

I know crown ethers can be used to complex metal ions. Question: What important properties do 18-crown-6 change during the benzannulation from 18-crown-6 to DB18C6 (dibenzo-18-crown-6)? How do these ...
1
vote
1answer
21 views

Properties of starch in packaged pudding

I had a mug of packaged pudding. The top layer of the pudding was of typical pudding consistency, while the bottom was more runny. What could have caused this?
0
votes
1answer
68 views

What will be the name of CH2=CH-O-CO-CH3?

We have this question in the textbook but there is no answer given and I have no idea how to name this compound. Edit: I tried naming the compound. Correct me if I am wrong here 1-Methylpropenoate
0
votes
1answer
50 views

Nucleophillic addition reaction in the presence of an acid catalyst on a molecule with an alkene

This is a solution for a question in my textbook. In the presence of an acid catalyst, am I wrong in my understanding that the acid will protonate the alcohol, and then do an electrophillic addition ...
2
votes
0answers
45 views

Do tertiary ethers tolerate oxidative workup of an ozonolysis reaction?

I am attempting to cleave a double bond into a carboxylic acid and carbon dioxide using an ozonolysis reaction followed by an oxidative workup. I am concerned with the presence of a tertiary ether in ...
4
votes
1answer
130 views

Reduction of amino acids to corresponding amino alcohols

I've stumbled upon an interesting article about reduction of amino acids and from there to reduction of L-valine to L-valinol using $\ce{LiAlH4}$ in THF. Article says that because of the cost of $\...
-4
votes
1answer
63 views

Best method to increase the chain length of allyl to butane-1,2-diol [closed]

Best method to increase the carbon chain length of allyl. and also add 2 OH carbon after reducing double bond give (S)-4-R-butane-1,2-diol and (R)-4-R-butane-1,2-diol . R= Any Ak, Cb, Cy, Hy
1
vote
2answers
198 views

Do SN1 reaction always result in Racemisation

In the following reaction the products formed are not enantiomers but are diastereomoers.So there is no racemisation occured.So is it always correct to say that SN1 result in racemisation?
1
vote
2answers
52 views

Is a liquid vitamin E supplement possible without additives? [closed]

Looking at E vitamin products sold commercially, all “pure vitamin E oil” products seem to be for skincare rather than consumption as a supplement. I have read that d-alpha tocopherol is the form of ...
0
votes
1answer
35 views

How to find the volume of the products in methane combustion?

The combustion of methane gas, $\ce{CH4}$, gives as products $\ce{CO2}$ and $\ce{H2O}$, both in the gas phase. If $1$ liter of methane is burned in the presence of $10$ liters of $\ce{O2}$. Suppose ...