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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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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 ...
Xlomer's user avatar
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-1 votes
1 answer
27 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 ...
new's user avatar
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2 votes
0 answers
36 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 ...
raptorlane's user avatar
-4 votes
0 answers
38 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 ...
Rakesh Ghosh's user avatar
-2 votes
0 answers
31 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?
Vibhas.D's user avatar
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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-...
vishesh jain's user avatar
3 votes
1 answer
325 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 ...
Jakub Nadažy's user avatar
-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 ...
Tejas Joshi's user avatar
3 votes
0 answers
37 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 ...
Flamma's user avatar
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3 votes
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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 ...
ASHISH's user avatar
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1 answer
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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, ...
Jakub Nadažy's user avatar
-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 ...
amys's user avatar
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-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 ...
Jo Nga's user avatar
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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 ...
Nightwing's user avatar
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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 ...
BugsBunny's user avatar
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 ...
user55119's user avatar
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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 ...
trerri's user avatar
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-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 ...
Yoojin's user avatar
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-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? ...
Natasha J's user avatar
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-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 ...
gsam7's user avatar
  • 25
-1 votes
2 answers
179 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 ...
urxwrt's user avatar
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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 ...
Carolina's user avatar
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 ...
Carolina's user avatar
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 ...
The Fright Of The Night's user avatar
8 votes
2 answers
857 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 ...
Nightwing's user avatar
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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 ...
Lindo Xulu's user avatar
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 ...
Ronith's user avatar
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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 ...
S K's user avatar
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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 ...
EMS's user avatar
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3 votes
2 answers
76 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 ...
trerri's user avatar
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2 votes
1 answer
42 views

What does ‘S/A’ mean in SMARTS pattern when using Chemicalize to draw the chemical structure?

I am still new to the SMARTS annotation. I am wondering what does S/A’ mean on the bond labeling drawn with Chemicalize using SMARTS [!#1]c1n[cH]nc([!#1])c1[!#1]? ...
tassaneel's user avatar
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-2 votes
0 answers
37 views

Amino acid methyl ester

Methanol is added into L-asparagine to form L-Asn methyl ester. HCl acid is added to catalyse esterification. Pyridine-2-carbaldehyde is added to form L-Asn Schiff base. NaOH is added to hydrolyse the ...
Guest's user avatar
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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 ...
Noor van den Berg's user avatar
1 vote
1 answer
66 views

Experimental determination of ring strain energy

For my thesis I am looking to expand a part of it to include experimental means of calculating ring strain, thus far I have calorimetry covering heats of combustion and hydrogenation as well as ...
nking1390's user avatar
2 votes
0 answers
30 views

Nonplanar polarization in allenes and aromatic compounds

I recently came across this elaborate article on electrophilic aromatic subsitution. In the third chapter "General mechanistic considerations in electrophilic aromatic substitution" the ...
jona173's user avatar
  • 567
3 votes
1 answer
194 views

What does ‘(A)’ mean in SMARTS pattern when using Chemicalize to draw the chemical structure?

I am not quite sure what ‘(A)’ could mean for the carbon atom when writing the SMARTS CCN(C)C using Chemicalize to draw the chemical structure below. Can anyone ...
tassaneel's user avatar
  • 131
-1 votes
0 answers
24 views

Delocalisation of electrons: Benzenecarboxylic acids

Naturally, the benzene ring will have a degree of delocalisation in the ring due to the pi cloud. Similarly, the carboxylic acid group will also have a degree of delocalisation. Correct me if Im wrong,...
Omar's user avatar
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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 ...
Bongo Man's user avatar
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-1 votes
0 answers
35 views

Why is Hoffmann product preferred over Zaitsev in this reaction?

[] Why is Hoffman product formed here in the elimination step in place of Zaitsev product? My guess is that adjacent double bonds are unstable for some reason In the next step $\ce{H^+}$ does not ...
ocresol's user avatar
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 ...
Indominus beaker's user avatar
1 vote
0 answers
49 views

Selection of parent chain in a halogenated compound with double and triple bonds

We were asked to select the parent chain for naming the halogenated compound containing double and triple bonds: My teacher told me that we choose the orange (1) one over the blue one (3) because as ...
Darshit Sharma's user avatar
6 votes
2 answers
150 views

What does ‘D’ in GADP (glyceraldehyde 3-phosphate) stand for?

Wikipedia says glyceraldehyde-3-phosphate can be abbreviated as G3P, GA3P, GADP, GAP, TP, GALP or PGAL, and many resources seem to use GADP as its abbreviation. I have no idea where ‘D’ came from. ...
chrononaute's user avatar
-1 votes
0 answers
31 views

Esterification reaction of acyl chloride with alcohol to give ester & HCl

Why we neutralize hydrochloric acid during the formation of ester by reaction of acyl chloride with alcohol using pyridine base. What if the acid is not neutralized? Will it affect the rate of ...
Ajit Yadav's user avatar
0 votes
0 answers
57 views

Restriction of back bonding in tris(dimethylamino)borane

J.D. Lee Concise Inorganic Chemistry [3, p. 78] mentions that The bond length order of the B-N bond in the following compounds is $\ce{B(NR2)3}$ > $\ce{HB(NR2)2}$ > $\ce{H2B(NR2)}$ and the ...
Chetan's user avatar
  • 69
1 vote
0 answers
46 views

Confusion in comparing contribution of resonance structures in Hydrazoic acid

Given below is the resonance hybrid of $\ce{HN3}$(Hydrazoic acid) And these are the resonance structures below: If the second resonance structure had contributed more, then the two bond lengths ...
Chetan's user avatar
  • 69
6 votes
2 answers
1k views

Retrosynthesis of 4-ethyl-2,2,5,5-tetramethyl-1,3-dioxane

I asked a similar question yesterday. They ask us to suggest a retrosynthesis for 4-ethyl-2,2,5,5-tetramethyl-1,3-dioxane I found this slide in our lecture where a dioxane is synthesized. If I ...
wengen's user avatar
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-3 votes
0 answers
18 views

What happen when the angle decrease than standard angle 109.5°? [duplicate]

I know when become less than 109.5° angle will cause angle strain that will reduce the stability of compound but why? ( I mean what is the reason decrease the stability of compound or what is the ...
M.J.S's user avatar
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5 votes
0 answers
115 views

Retrosynthesis of 2,5,8-trimethylnonan-5-ol

They ask us to suggest a retrosynthesis of 2,5,8-trimethylnonan-5-ol: So I went through my course slides, and I found this: Translation: verwende Grignard = use Grignard My question is: Can I ...
wengen's user avatar
  • 423
0 votes
0 answers
47 views

Melting Point Order of Benzene Derivatives

Q)Compare the melting points of the following? o-Hydroxybenzaldehyde o-Methoxybenzaldehyde p-Hydroxybenzaldehyde p-Methoxybenzaldehyde My attempt: Intermolecular H-bonding increases melting point ...
Chetan's user avatar
  • 69
-2 votes
0 answers
43 views

Aromaticity in Carbene compounds?

how do i check aromaticity in carbene molecules? i have never come across such a question and am not even sure if huckel's rule is valid here. any help would be appreciated!
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