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.
10,205
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Conjugate addition of alkyl groups to α,β-unsaturated Aldehyde [closed]
why the conjugate addition of an alkyl or other organic group to an α,β-unsaturated aldehyde is not available while ketones can? (for example of addition of lithium diorganocopper reagent, R2CuLi)
3
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0
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34
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Systematic method to determine D/L notation of substances other than amino acids and glyceraldehyde
The fundamental rules of D/L notation, as I understand it, are as follows;
In D/L notation, a molecule is named by mapping it to glyceraldehyde.
The D/L notation is based on the stereo configuration ...
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3
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1
answer
120
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If the substituents are distinguishable, is it possible to prioritize them using the CIP rules?
In the R/S stereochemical nomenclature,
when we try to determine the priority of substituents around a chiral carbon, are there specific examples where the ranking cannot be definie under the CIP ...
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2
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1
answer
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IUPAC name of the following bicyclic / spiro compound
We have the given compound
It's IUPAC naming is more sinister than things seem.
It's not a proper bicyclic compound, or a proper spiro cpmpound either.
I could interpret the spiro compound in red, ...
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1
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42
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Synthesizing "Methyl 2-(2-oxopyrrolidin-1-yl)-2-phenylacetate" [closed]
I am a chemistry student, here I mapped out the steps one might take to synthesize Methyl2-(2-oxopyrrolidin-1-yl)-2-phenylacetate, a piracetam dirivitive. Please add any steps I might be missing and ...
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1
answer
23
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Fischer Esterification and Dean Stark
Why is it Impossible do use a Dean Stark Montage if our reactives are more volatile than the mixture (H20 + Toluene for example)
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Does acetone react with acidic precipitate product in this reaction?
In this reaction procedure, It seems like there is a mistake in step 3 which would result in a 0% yield. From step 3, it looks like everything is fine, its performing the acid catalysed hydrolysis of ...
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0
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Nucleophilicity in protic solvents
It is said that a weak base acts as a strong nucleophile in protic solvents because it has less dipole-dipole interaction, so following that analogy, we can say that F- is a weak nucleophile than I- ...
-1
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1
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45
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Nutrients in translucent bottles/boxes
Nutrients e.g vitamin C, calcium etc are sensitive to light and that is the reason that major companies have juices and milks in boxes and opaque packages.
But there are some companies that the recent ...
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3
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136
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Structure of AgNO2 and AgONO [closed]
We had a discussion in class today about the substitution reaction of RX with AgNO2 and KNO2. Pretty unimportant, since those seem just fine. But there were 2 arguments.
The root problem was, that we ...
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3
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1
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208
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Product of oxymercuration-demercuration reaction
What will be the major product of this reaction?
I know that this is the OMDM reaction where Alkene is converted to alcohol following the Markovnikov rule. This question is also atypical because all ...
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1
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1
answer
73
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Naming of cyclic acid anhydrides
For some cyclic anhydrides, the -dioic anhydride suffix seems to be used.
E.g. butanedioic anhydride (succinic anhydride).
How does this apply to anhydrides which are not symmetrical about the oxygen ...
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1
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0
answers
39
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Organic Chemistry: Numeric prefix for 9 carbons doesn't follow pattern of greek numbers [duplicate]
In the nomenclature of organic compounds, a numeric prefix is used for denoting the number of carbon atoms in the main structure. From "pent" onwards, they seem to follow a pattern of greek ...
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3
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0
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Hydrolyse Phosphonate diester to free phosphonic acid under relatively mild conditions?
I want to hydrolyse a phosphonic acid diethylester to the corresponding free phosphonic acid. In the literature, it is described, that usually strongly basic or acidic conditions are utilized to ...
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1
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1
answer
67
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Which of the following two IUPAC names would be accurate according to 1993 IUPAC rules?
I'm not looking for answers that are based on 2013 IUPAC recomendation based rules. But rather the old 1993 rules of IUPAC.
The two names are :
1.) Penta-1,2-dien-5-ol
2.) Penta-3,4-dien-1-ol
would we ...
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1
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0
answers
77
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Why did this synthesis of Aspirin fail?
I tried to synthesize acetylsalicylic acid(aspirin) by the method below. However, I definitely failed and got something unknown.
The method used was:
Add 2.5 g of salicylic acid(about 2494 mg), 3.0 ...
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1
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0
answers
76
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Aminium/Ammonium?
Chemdraw names this as 2-carboxyethan-1-aminium. Shouldn't it be ammonium? What's an aminium ion?
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2
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113
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Why don't Alkyl Fluorides form Grignard Reagents
The reactivity of forming Grignards reagent were given as RI > RBr > RCl > RF and was noted that Grignard reagent with alkyl fluorides cannot be formed. What is the reason for this?
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4
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2
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574
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Acidity of metronidazole
Metronidazole has two $\mathrm{p}K_\mathrm{a}$ values: $2.57$ and $15.42.$ The basic group is the imidazole moiety. Does metronidazole have acidic groups?
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3
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1
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72
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Reduction of di-N-substituted imidazole to imidazoline to remove counterion?
I would like to synthesize a di-N-substituted imidazole (compound 4) in its free base form or reduce it to generate an imidazoline (compound 5) to remove the bromide counterion to the imidazole ring.
...
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3
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0
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51
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Boiling point of pentanol isomers
Arrange the following alchohols and alkanes in increasing order of boiling point:
3-pentanol, n-pentane, 2,2-dimethylpropanol, n-pentanol
I understand that n-pentane would have the lowest boiling ...
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0
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1
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94
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Friedel-Crafts alkylation of fluorochloropropane
Consider benzene reacting with 1-chloro-3-fluoropropane, with $\ce{AlCl3}$ as the Lewis acid. My question is, is this reaction feasible? If so, what is the product formed and do cationic ...
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1
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0
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63
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Why do vinylic carbocations have an empty sp2 orbital instead of an empty p orbital?
Assume a tetrahedral carbon with a leaving group reacts via the SN1 mechanism. This carbon is initially sp3 hybridized, and after the departure of the leaving group, the resulting tertiary carbocation ...
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1
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95
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Mechanism of ring expansion of epoxide
The below transformation is from
J. Am. Chem. Soc. 1990, 112, 14, 5583–5601
What does the treatment with lithium anion of ethoxyacetylene in the presence of the lewis acid do to epoxides? How does ...
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1
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1
answer
176
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Why doesn't the reaction between molecule "B" and diethyl oxalate yield a diester?
Problem
Answer
Question
Why isn't this structure the answer for the second reaction?
From my understanding, the resonant structure (B) with the full negative charge on the oxygen is the most stable ...
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1
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1
answer
106
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Why doesn’t the reaction between 3-mercaptopropionic acid and methyl iodide yield a methyl ester? [closed]
Problem
Answer
Question
I don’t understand why 3‐methylthiopropionic acid (X) is the correct answer. Wouldn’t sulfur and carbon have similar electronegativities?
As the consequence, isn’t it more ...
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3
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0
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80
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Gabriel Phthalamide Synthesis of 1-Phenylethylamine
I had learnt that due to the nature of the Gabriel synthesis reaction being $S_{N}2$, the alkyl halide used must have a primary alkyl group. However, in an exam (JEE Main 2023), it was mentioned that ...
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0
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28
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Factor affecting acidity:Hybridization [duplicate]
I have problem here
So I had learn that the percent of s-character of hybrid orbital will affect the bond strength. The higher percentage of s-character,the stronger the bond.For example the strength ...
3
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1
answer
165
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Ring formations catalyzed by piperidinium acetate: Robinson annulation?
Hey everyone, I have a question about the mechanism below. Do you guys think the Robinson annulation is a good starting point for the 6-C ring on the right? If not, what would you suggest me for this ...
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1
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Na+ as an electrophile [closed]
In inorganic I learnt that s block cations are lewis acids but while learning attacking reagents in organic chemistry I came across the fact that Alkali metals are not electrophiles, why so?
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0
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50
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Degradation of 4-MeO-Tetrahydrocarbazole
I recently synthesized 4-Methoxy-Tetrahydroxarbazole from 4-MeO-Phenylhydrazine and Cyclohexanone. The product had a off-white color directly after synthesis but was brown after standing over night at ...
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0
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54
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Order of radical dimerization ability
In a question I came across recently, it was asked to arrange the following radicals in the ascending order of dimerization ability.
I have read about the triphenylmethyl radical undergoing Gomberg ...
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0
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63
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How to break C-C bond in a cyclohexanone?
I cannot find a way to start this reaction. For the end, I found that a H that is attached to C with OTs group will be deprotonated forming double bond but before that I think I need to break C-C bond ...
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0
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Synthesis of 1-ethylcyclohexane-1,2-diol from cyclohexylethene
Here's my synthesis:
HBr
NaEtO
OsO4/NMO
But the problem is that for step 2, there are 3 possible alkene locations, with all of them having 3 substituents, so I would have all 3 forming (although 2 ...
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1
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2
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324
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What determines the location of nucleophilic attack on a conjugated ketone or aldehyde?
In a conjugated ketone or aldehyde, nucleophiles could attack the double bond or the carbonyl carbon. I have two examples that differ in the location of initial attack, and I am wondering what ...
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0
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Find the missing chemical structures in the reaction sequence
I came across the following question, where a set of reagents are used, starting from a carbohydrate derivative.
I understand that this is some total synthesis reaction, but I cannot find which one.
...
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1
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1
answer
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Help with Calcium Alginate Precipitation
I am a high school student working on a research project that involves producing alginate gel directly from wet seaweed. I am starting the first phase next week, which is using a small batch to ...
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0
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24
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Is -NR3+ really meta directing? [duplicate]
For electrophilic aromatic substitution, it is said that -NR3+ is meta directing, but since it only shows electron withdrawing inductive effect and inductive effect decreases with distance so it must ...
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0
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Hybridization and lone pairs
I understand how hybridization works but have trouble understanding it conceptually. I understand that for bonds to form, the electrons must be in orbitals with equivalent energy, but why does this ...
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2
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1
answer
70
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A reduction of an ester with DIBAL-H to alcohol
I will do a reduction with DIBAL-H and after I need to do the workup of this reaction. I have to quench the reaction with MeOH at 0°C.And I will let the reaction return to rt. As shown below :
I'll ...
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0
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What's this reaction converting 9,10-dihydroanthracene into anthracene
I have no idea what this reaction converting 9,10-dihydroanthracene into anthracene is. Could someone help me with the name of the reaction/ or explain the mechanism of the formation of the product? 9,...
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0
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Difference between acid-catalysed iodination of acetone and the iodoform reaction
I am curious about what makes the iodoform reaction (in alkaline conditions) substitute 3 times whereas the iodination of propanone (acidic conditions) only substitutes once. Or am I just completely ...
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1
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Selective formation of enolates
I saw the following reaction on Modern methods of Organic Synthesis by Carruthers. The reaction is about the selective alkylation of trimethylsilyl enolates, and is shown below.
However, I have some ...
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1
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Can I make orthophosphoric acid from sodium dihydrogen phosphate and an acid which I can use to make ethyl iodide?
For my project I needed to di-substitute benzamide with ethyl group at N position to create DEB as a mosquito repellent. The first part of creating benzamide I was able to do, but the second part of ...
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1
answer
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Which hydrogens are the most acidic in a THF molecule?
Which hydrogens are the most acidic in a THF molecule? I understand the main factors that influence acidity, but I can't seem to figure this one out and I have not gotten any answers on the internet.
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0
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Amidine synthesis from nitrile and dimethylamine using n-Buli as a base
I am making LiNMe2 using n-Buli (5.5 equiv.) and dimethylamine (5.0 equiv), -15 ºC, dry THF and under nitrogen atmosphere.
I have been doing the reaction and I can observe conversion of starting ...
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11
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3
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Why does burnt milk on bottom of pan have 'vaguely' cork-like pattern?
I burnt milk while boiling it. I noticed that the burnt milk on the bottom of the pan, formed a pattern that vaguely resembled the pattern of cork-cells . Why is this pattern being formed?
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0
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50
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Which enantiomer of 3-Chloro-2-pentanol is this?
I think that there is a chiral centers at $C_2$ and at $C_3$ (Numbering starting such that the carbon with hydroxy attached is number 2.
Then, for $C_2$:
Priority would be: OH > $C_3$ > $C_1$ &...
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0
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0
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Why do grignard reagents add to carbonyls at the carbonyl carbon, and not deprotonate at the alpha carbon to form an enol? [duplicate]
I thought that since grignards are such strong bases that they would be immediately protonated by the alpha hydrogen since it is an acidic hydrogen. However, I keep seeing answers that are saying that ...
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1
vote
2
answers
76
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Mechanism of deprotection of enol thioether
I was reading some enolate chemistry from Carruthers textbook and came across the selective alkylation of unsymmetrical ketones. The reaction involves blocking one alpha-position of the ketone using ...
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