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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.

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-1 votes
0 answers
14 views

Determing a monomer in a polymer

Do monomers can be determined by me? It depends on the location which I start. It is sketched at the picture.
0 votes
0 answers
43 views

Conflict: Sandmeyer reaction and Gattermann reaction

So it is known that benzene diazonium chloride when reaction with cuprous(I) chloride would produce a chlorobenzene which is called Sandmeyer reaction. Now for the same salt, if we react it with ...
-1 votes
1 answer
33 views

Why does pectin/agar jelly taste sweet, if they stay solid at 36.5 °C, entrapping sugar?

When we eat pectin jelly(fruit jelly) or agar jelly, they taste sweet. This should imply that sugar entrapped in gel network is somehow exposed and dissolved to saliva. However, pectin and agar gel ...
2 votes
0 answers
37 views

(Di)chlorination of phosphonic acid ester

What is the best way to do this reaction to form the dichloride as an reactive intermediate when the substituent R is acid sensitive? In the literature the reaction is either performed with PCl5, a ...
-4 votes
0 answers
39 views

what will be the major product on mononitration of para-isopropyltoluene? [closed]

para-isopropyltoluene means an isopropyl group attach to the para position with respect to the methyl group of toluene. mononitration means treating with concentrated HNO3 and concentrated H2SO4 to ...
3 votes
1 answer
328 views

It is possible to synthesize 3,3-diethylpentane ("tetraethylmethane") from carbon tetrachloride?

Compounds like tetraethyl silane or tetraethyltin can be made from their tetrachlorides using ethylating Grignards, but what about substituting carbon, would it work or steric hindrance would prevent ...
-4 votes
0 answers
56 views

What's the correct name of this compound ..?

In an exercise for naming organic compounds, the compound shown below is named “3-ethyl-6-methylcyclohexene” in my textbook and even on Pubchem (https://pubchem.ncbi.nlm.nih.gov/compound/3-Ethyl-6-...
-2 votes
0 answers
33 views

Why can't benzene carbocation be stabilized by resonance effect?

I've seen that carbocations of cycloalkenes and those of benzene attached to more carbon atoms can be stabilized by resonance. Similarly, why cant benzene carbocation be stabilized by resonance?
-2 votes
0 answers
34 views

Grignard reagent addition to carbonyl compounds [closed]

How does Grignard Reagent shows the addition reactions with carbonyl compounds? I'm having problems in the mechanism of the reaction. I know that Grignard reagent is a very versatile reagent apart ...
1 vote
1 answer
58 views

Does di(n-propyl)ether support Grignard reactions?

It is known that diethyl and dibutyl ethers are good solvents for Grignards, it has been also found that diisopropyl ether does not work. I have never seen dipropyl being discussed. Edit: For clarity, ...
3 votes
0 answers
54 views

Is cyanomethanide more stable than 2‐oxoethanide?

Which carbanion is more stable? $$\underset{(\textbf{a})}{\ce{H2\overset{-}{C}-CN}} \qquad \underset{(\textbf{b})}{\ce{H_2\overset{-}{C}-CHO}}$$ If we talk about the −M effect, $\ce{CN}$ is higher ...
6 votes
2 answers
558 views

Do alkyl halides with an alpha nitrogen atom undergo SN1 reaction?

Today, in my organic chemistry class, I learnt about the nucleophilic substitution reaction. The notes have stated that: Alkyl halides with $\alpha$ oxygen atom can also undergo SN1 reaction ...
1 vote
1 answer
34k views

Does Rubbing Alcohol + Bleach really produce Chloroform?

A lot of sources on the internet claim that mixing rubbing alcohol with chlorinated bleach produces chloroform. Rubbing alcohol is Isopropanol, and bleach is Sodium Hypochlorite. Neither of these are ...
3 votes
0 answers
38 views

How to decide the correct numbering of aminocyclohexenol?

I'm self studying for a university admission exam. So I'm relying fully on online sources to study, but I often get confused because of differing methods. This is one such case: According to this ...
-6 votes
0 answers
62 views

What is an organic compound with 32 isomers? [closed]

I'm in grade 11 chemistry and learning organic chemistry. My teacher said that we will get bonus marks on our exam if we are able to name all 32 isomers of a compound, so I was hoping that someone ...
-3 votes
0 answers
19 views

Nucleophilic Addition reaction mechanism [closed]

In the reaction of Acetaldehyde with HCN, why is the CN(-) added first and not the H(+) ion. The mechanism is NUCLEOPHILIC ADDITION, but otherwise what could be the reasons. My textbook didnt mention ...
1 vote
1 answer
113 views

Cannot understand the stereospecificity and stereoselectivity of a compound formed in a reaction

How is the reaction given below stereospecific and stereoselective? 1,3,6-trimethylcyclohexene is treated with B2H6 followed by H2O2/NaOH/H2O. Since trans and cis form in cycloalkene starts in a 8 ...
0 votes
0 answers
26 views

Why does allylic bromination occur with N-bromosuccinimide?

For the purpose of allylic bromination on an alkene, say propan-1-ene, N-bromosuccinimide (NBS) is added to HBr in carbon tetrachloride which leads to the formation of bromine. The bromine, in the ...
0 votes
1 answer
41 views

Do Electron-Withdrawing-Groups give an hypsochromic shift or a bathochromic one? and why?

I'm not familiar with this topic,but i know that bathochromic shifts occur when the energy gap between energy levels of the substituted molecule, are lower than the unsubstituted one;viceversa ...
1 vote
1 answer
75 views

Dehydration of isoborneol with carbocation rearrangement

What rearrangement happens when isoborneol (structure below) is heated with acid? Since acid is used and the hydroxyl group is present, the reaction mechanism is dehydration. My attempt: In the ...
-1 votes
2 answers
180 views

What is the chemical reaction between nitric acid and acetic acid?

Is there a chemical reaction between nitric acid and acetic acid? The main reason I am asking this question because my lab throws away residues of both of these two ($\pu{1 M}$ concentration each) in ...
6 votes
0 answers
73 views

Another Issue With ChemDraw?

Two years ago I posted issues with erroneous stereochemical assignments made by ChemDraw (CD). To date, the people at ChemDraw have not resolved the issue. Recently, I have uncovered an error with a ...
3 votes
0 answers
43 views

Can thionyl chloride or similar be used as catalyst for Hell–Volhard–Zelinsky halogenation?

Since the mechanism for the Hell–Volhard–Zelinsky (HVZ) reaction involves a phosphorus trihalide in catalytic amounts solely to form the acyl halide of the reagent, couldn't a different catalyst be ...
1 vote
1 answer
556 views

Twisting stereoisomers with rings to determine R/S [closed]

I know that if the smallest atomic number group is not in the back, we can twist the molecule so that it is in the back and then determine if it is R/S (Left image). But if the chiral center is ...
8 votes
1 answer
4k views

How can this ketone show Cannizzaro reaction?

According to answer key, Cannizzaro reaction of 3-hydroxy-2,2-dimethyl-1-phenylpropan-1-one (a ketone) takes place but how is that possible when we know only aldehydes show Cannizzaro reaction?
7 votes
6 answers
3k views

How can I determine the size of tropolone molecule?

How can I determine the size of a tropolone molecule? It's a seven-membered aromatic ring with =O on the first carbon and -OH on the second carbon. Is there any software available?
-1 votes
0 answers
49 views

Studying for organic chemistry, i'm completely new and confused. is there any chronological order to study this, any tips and advice to excel? [duplicate]

I really want to excel in organic chemistry, I'm completely new to it and my teacher doesn't teach well. Is there any source, tips and advice to understand and excel in organic chemistry? Because it ...
-2 votes
0 answers
64 views

Getting enantiomers from the same molecule written differently?

This is a reaction I have written in my notes: I get $(A)$ from the upper molecule and $(B)$ from the lower molecule. $(A)$ and $(B)$ are enantiomers. My question is why are the products enantiomers? ...
13 votes
2 answers
1k views

Does folic acid contain a benzyl or a phenyl group?

I'm studying for my MCAT currently and I stumbled upon this question. It gives the structure of a folic acid molecule and asks what functional groups can be found within the molecule. I understand ...
-2 votes
0 answers
55 views

Is this calculation of number of bonds formula correct? [closed]

I found this formula in a book but I am unsure if this is correct. There is no derivation whatsoever given. I have tried using it but cannot reach the solution In open-chain compounds: Number of ...
1 vote
0 answers
35 views

Lignin Test mechanism for amine identification

So, I've been trying to find a mechanism to explain the Lignin test for amine identification but haven't had any lucky so far. I was wondering if anyone here might know the mechanism? In the procedure ...
3 votes
0 answers
43 views

Reaction of aniline with sulfuric acid

I'd like to know why a compound I had, when reacted with concentrated sulfuric acid during an identification test, produced a solid compound that appeared carbonized (the solid was grey). After ...
4 votes
0 answers
70 views

Will 1-phenylpropan-2-one give the iodoform test?

The iodoform test involves an acid base reaction with NaOH in which the alpha hydrogen atoms (hydrogen atoms on carbon 3) react with hydroxide ions followed by substitution of iodine. This is expected ...
8 votes
2 answers
859 views

Why does the Wurtz-Fittig reaction occur?

In the Wurtz-Fittig reaction, an aryl halide and an alkyl halide react with sodium in the presence of dry ether to give R-Ar as the major product. Why is the coupling of R and Ar favoured? In other ...
2 votes
2 answers
117 views

How to identify an organic base?

According to the answer key, trimethylamine (iii) and ethanolamine (iv) are considered organic bases, whereas ammonium (i) and acrylamide (ii) are not: From my understanding, an organic base has an ...
5 votes
1 answer
428 views

Is cyclohexane‐1,3‐dicarboxylic acid a correct IUPAC name?

I did the numbering by taking all the functional groups in principal chain (scheme A), but my teacher did it differently and proposed the name cyclohexane‐1,3‐dicarboxylic acid (scheme B): The ...
10 votes
2 answers
351 views

Can ferrocene type sandwich compounds be made with fluorene?

Ferrocene will be well known to made members of this site. It consists of two cyclopentadienyl anions sandwiching an iron-II ion. During my first year organic chemistry course (about 40 years ago) I ...
4 votes
2 answers
9k views

Reaction mechanism for 7-hydroxy-4-methylcoumarin synthesis with an iodine catalyst

7-Hydroxy-4-methylcoumarin can be synthesized from ethyl acetoacetate and resorcinol with iodine as a catalyst. What is the mechanism for this? From what I understand it follows the Pechmann reaction ...
0 votes
0 answers
22 views

Metronidazole physicochemical characteristics [duplicate]

In literature it is not clear whether the drug metronidazole is acidic or basic. However the British pharmacopoeia indicates that an aqueous saturated solution of metronidazole has a pH of 5.8. This ...
5 votes
2 answers
123 views

Synthesis of (S)-2-hydroxy-4-oxohex-5-enal

I am currently working on a total synthesis strategy, but I was told that a key step in my total synthesis probably wouldn't work, so now I am trying to figure out a way around it. The compound that I ...
5 votes
0 answers
668 views

How does a photochemical reaction of lignin with oxygen (yellowing of paper) produce chromophores?

Edit: This question is about chromophore production in lignin as found in low cost or short-term use paper such as newsprint. A different, excellent answer describes oxidation yellowing of the ...
6 votes
2 answers
3k views

Étard Reaction of Ethylbenzene

What is the major product when the following compound undergoes Étard reaction? Is it acetophenone or a terminal aldehyde. The mechanism discussed in Mechanism for an Étard reaction (chromium complex)...
3 votes
2 answers
77 views

What does phosphorodibromidous acid do in solution?

When tribromophosphine is used to activate an OH to enable its substitution, the leaving group is listed by PubChem as "phosphorodibromidous acid" and doesn't seem to really exist from a ...
1 vote
1 answer
87 views

Are there methods of synthesizing rubber from plant materials?

First and foremost, I am not talking about natural rubber. I am asking if there are any industrially used methods of synthesizing rubber from agricultural products as opposed to synthesis of rubber ...
10 votes
2 answers
949 views

Risks of restoring old books from decaying

I was reading this article on " Why Do Old Books Smell So Good?" and I came across a part of it that seemed to be not elaborated upon. Rapidly degrading and at-risk documents that are ...
5 votes
2 answers
1k views

Total number of stereoisomers of truxillic acid

Total number of stereoisomers of the compound will be: This was a question asked in our mock test. I've tried by considering pseudo-chirality on the carbon atoms. But I don't know where to start. I ...
0 votes
0 answers
44 views

Why is α-truxillic acid not meso compound? [duplicate]

I know that for a compound to be meso it should be optically inactive and should have multiple chiral centres but in case of α-truxillic acid, it is optically inactive due to centre of symmetry being ...
3 votes
1 answer
120 views

Why is Piperidine more basic than Pyridine? [duplicate]

Piperidine, which has sp3 carbons attached to it, experiences an increase in electron density on the nitrogen atom, making it more basic. However, when we look at the resonating structures of pyridine,...
3 votes
1 answer
680 views

Reaction of 1,3-butadiene with HBr in the presence of peroxides

I have learnt that the reaction of 1,3-butadiene with HBr depends on the temperature as the temperature determines whether the reaction is under kinetic or thermodynamic control. I believe that this ...
0 votes
1 answer
35 views

What is the major product formed when you react 1,3-butadiene with HBr in the presence of both ROOR and heat? [duplicate]

I just had an exam where we were given 1,3-butadiene as our reactant and our major product as 1-bromo-2-butene, where we had to state what the reagent was for that particular reaction. I stated that ...

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