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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Help with this mechanism? [closed]

I know that the bottom reaction is probably elimination, but I've never seen Na2CO3 being used as a reagent in this context. I've only taken Organic chemistry I and II, so that's the extent of my ...
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1 vote
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Preventing solvent evaporation for small scale synthesis

I have been conducting an organic synthesis with quite expensive starting material, so whenever I setup the reaction I only use 0.1 g of starting material. I use 4 mL of toluene to adjust the ...
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2 answers
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Boiling point of C3H7Cl vs C2H5I

I know that boiling point of alkyl halide is proportional to the length of the alkyl group, and that the order of BP is RI > RBr > RCl > RF for an alkyl group R. But which of the factors is ...
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-2 votes
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Is Hydroxypropyl Methylcellulose an ok substitution for Hydroxypropyl Cellulose? [closed]

I'm trying to make these https://www.nature.com/articles/s41467-022-30505-2 , and it calls for HPC which is significantly more expensive then HPMC, is it ok to substitute ?
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Find concentration of ammonium and ammonia when 0.5 mL 25% ammonium hydroxide is mixed in 1 L H2O at 20 ºC

Doing an experiment where I do as the title says, but am struggling to know the right way to calculate the concentration of NH3 and NH4+. Ammonia 25% (Density: 0.91 kg/L, Mwt: 35.05 g/mol) One thing i'...
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5 votes
1 answer
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Synthesizing octopine from arginine and 2-bromopropionic acid

I am a biologist, and organic chemistry lessons are a distant memory now. I am interested in synthesizing a small amount of octopine. Octopine is a natural molecule resulting from an enzyme-catalyzed ...
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Is the following titration possible (titration of a ketone via oxime formation)?

Given the molecule below (its a salt consisting of a tosylate), I was wondering if the following titration, which can be used for aldehydes and ketones, would be possible in theory: Add excess ...
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1 answer
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Reimer-Tiemann reaction of aniline

[how reaction actually happens I wonder is it possible for aniline to undergo Reimer-Tiemann reaction just like phenol? What is the problem in that? How to compare rates of carbylamine reaction and ...
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1 answer
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About stability and reactivity? [closed]

it has been said by my teachers and even in internet that tertiary carbocation is more stable than secondary my question is if it more stable then why does it forms products?
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6 votes
1 answer
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Does methyl or aldehyde group have higher priority when choosing the main chain of carbonyl compound?

As far as I know, both following names seem to be correct for the compound below. Please explain which IUPAC name is correct by which IUPAC rules: 4-formylpentanoic acid (methyl group counted in the ...
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1 vote
1 answer
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Does the 3D structure generated with MolView violate the wedge-dash rules of "above/below the plane"?

I've been taught that in a wedge-dash diagram, the wedge represents a bond above the plane of the paper, and the dash represents a bond below the plane. Accordingly, I expected the structure of this ...
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1 answer
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Why does acetone give a positive test in Tollens test? [closed]

Tollens test is used to distinguish between ketones and aldehydes wherein it oxidizes aldehydes into a carboxylic acid (according to my textbook). However, another book says acetone gives a positive ...
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3 votes
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Compound's reactivity in Hoffman Bromamide Reaction

I already know that the presence of electron donating groups in the soon-to-be migrating group in the Hoffman Bromamide reaction makes the molecule more reactive, but I encountered a question which ...
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-2 votes
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how to make KMnO4 miscible in octanol? [closed]

I just wanted to have a homogenous mixture of octanol and KMnO4 , so what are the factors or conditions that i have to keep to achieve the desired solution.
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SN2 and E2 Reactions with Primary, Secondary, and Tertiary Alkyl Halides

I was wondering if there are any substitution products present when a strong base/weak nucleophile (such as tert-butoxide) reacts with a primary or secondary alkyl halide. I know that the E2 products ...
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Aromatic nucleophilic substitution of benzyne with amine

All the books say that we can have aromatic nucleophilic substitution by benzyne with strong base like $\ce{NH2-}$. Anyway, I've never seen another base. For example, can we have ARn with 1-...
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Determination of the most basic nitrogen atom in the given molecule [closed]

In the molecule pictured on the photo, nitrogen atom number 7 looks the most basic. It is 2 degree, the lone pair is localized and there is no resonance, so it should accept the proton readily. But ...
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0 answers
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Percentage yeilds of the reaction between tert butyl bromide and silver nitrite

I know that, $$ \ce{R-X + AgNO2 -> R-NO2 + AgX} $$ I have been taught that here nitro alkanes are major than nitrite esters and I have also been taught that this reaction proceeds through SN1 ...
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7 votes
1 answer
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Reaction between 1,2-bis(buta-1,3-dien-1-yl)cyclohexan-1-ol and potassium hydride in THF

Which product is formed in the following reaction? I am quite certain that we deal with an oxy-Cope rearrangement that works at room temperature, but I don’t know how to draw the product given the ...
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0 votes
2 answers
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Shouldn't the Cl- be placed beside the charged N+ ion when writing the structural formula of Benzenediazonium chloride?

I found the structural formula of Benzenediazonium chloride written on a website: I believe that the Cl- ion is stabilizing the N+ ion. So, shouldn't the structural formula be written like the above ...
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2 votes
0 answers
48 views

Nylon 6,6 synthesis yield

This is the nylon 6,6 reaction Having these data available, I would need to know the theoretical quantities, in grams, of the monomers My attempt: Adipoyl chloride is our limiting reactant so ...
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1 vote
0 answers
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Does E1cB take place over here?

I formed this product (reason: alkene has 6 alpha hydrogens) ----> However, it turns out, this is the answer: The reason why I suspect this is e1cb is because NO2 could stabilize the carboanion (...
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-2 votes
1 answer
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How to name this organic compound?

How would you name, if ethoxy ethane is disubstituted with hydroxy group on both alpha carbons? Here is it's formula, $\ce{H3C-CH(OH)-O-CH(OH)-CH3}$ Is this compound stable at room temperature or not?
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1 vote
1 answer
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Why is p-dichlorobenzene the major product of chlorination of chlorobenzene?

The chlorine atom in a chlorobenzene has an ortho- and para- directing effect on any further substitution by an electrophile. Going by probability ortho- position has 2/3 chance and para- position has ...
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3 votes
0 answers
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How to establish trend of carboxylic acid acidity in the presence of certain substituents?

I encountered a question in my textbook which asked the following: At first, i thought that i can approach it in the same way i sort the effect of EDG and EWG on the acidity of phenols, that is, ...
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-2 votes
1 answer
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Does sodium borohydride reduces alkyne? [closed]

Will an isolated Alkyne or an alkene be reduced using sodium borohydride ($\ce{NaBH4}$)?
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3 votes
1 answer
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What is the pKa value of the nitrogen atoms, specifically the amine groups?

How would you estimate the $\mathrm pK_\mathrm a$ values of the nitrogen atoms in 1,4-dimethyl-1,2,3,4-tetrahydroquinoxaline? I struggle with it because I am unsure whether to classify them as ...
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reason for Popoff's rule [duplicate]

Popoff's rule, unless I'm mistaken basically states that when a chain containing a carbonyl carbon is oxidised, on fragmentation the carbonyl group(C=O) is retained by the smaller chain. Is there any ...
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1 vote
1 answer
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How is the intermediate compound 2-chloropropan-1,3-diol is formed when hypochlorous acid is added to allyl alcohol in the preparation of glycerol?

The expected product is 3-chloropropan-1,2-diol since secondary carbocation is more stable than primary but it is not formed. I have surfed the internet a lot regarding this and none seems to be a ...
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0 votes
1 answer
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What is the Chemical Reaction that Explains why Rubbing Ascorbic Acid on Rust Stains Removes Them?

I am a pool maintenance technician. In the industry, we pour bags of Vitamin C (ascorbic acid) into the pool to remove rust stains from the fiberglass surface. I am trying to determine the chemical ...
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-1 votes
1 answer
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Formula of what substance is shown in the clip Disappointed by Electronic? [closed]

I'd like to know the substance (if any) the model of which is shown in the clip Disappointed by Electronic. The following screenshot is taken from the video electronicofficial — Electronic - ...
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1 vote
1 answer
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Negative Fehling's Test for glyoxal and glyoxylic acid

While I understand why aromatic aldehydes and ketones do not give positive Fehling's test, I do not know why Glyoxal and Glyoxylic Acid give a negative test too. Nothing has been written about these ...
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0 votes
0 answers
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name of these compounds?

I'd call c. 6- (3 aminocyclohexyl- methylamino) cyclohexa-2,4-dien-1-one and d. 1r, 2s- 2 (2-formyl- 4-methoxycarbonyl-but-3-en-1yl) cyclobutanecarboxylic acid
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1 vote
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What kind of rearrangement happens between 2,2,5-trimethylcyclopentanol and concentrated sulfuric acid?

Question: My attempt: After getting the carbocation after protonation, in order to form a more stable alkene, it rearranged the methyl group on the adjacent carbon so as to get the alkene in the ...
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0 votes
1 answer
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How does the molecule consisting of two bridged aromatic rings look in 3D?

I can't understand how the following compound with bridged benzene rings looks like:
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1 answer
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intramolecular h-bonding in maleic acid

While studying organic chemistry, I came across two practice questions given by my professor: Compare the acidic strength of:- Maleic acid and Fumaric acid o-nitrophenol and p-nitro phenol And the ...
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-2 votes
0 answers
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Is the first letter of the first substituent capitalized? [duplicate]

Which of the following is correct? 4-Bromo-1-chloropentane or 4-bromo-1-chloropentane 3-Methylhexane or 3-methylhexane 2,2,5-Trimethylhexane or 2,2,5-trimethylhexane I'm asking this because my ...
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0 votes
0 answers
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Quantity vs quality in determining acidic strength

Consider the following order of acidity based on pKa values:- ethanoic acid > phthalimide >phenol >water >acetamide Looking towards similar questions on stack exchange such as this , the ...
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1 vote
0 answers
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Phenol's resonance structure doesn't match NMR

I've asked a question before and quickly realised that the resonance/mesometric effects played a large role in determining the C-13 NMR spectrum of phenol, shown below. This is the resonance ...
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1 vote
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Why is a strongly-ortho directing substituent preferred over a strongly-meta directing substituent?

When we were taught electrophilic aromatic substitution at our school, our teacher made us write the "rules" of di-substituted benzene concerning the decision of the substitution position ...
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Why do some nucleophiles attack at the carbonyl group while others at an alpha-carbon?

I was observing the following reaction: The only part I am confused on is the first step... why does the peroxide oxidize the reactant by attacking the alpha carbon of the carbonyl ester instead of ...
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0 votes
0 answers
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Why are amides weaker acids than water?

Based on a a recent question I asked on ChemSE, the answer to my question was that amides are weaker acids than water with a typical pKa value of ~20. Although, this answers my question, it got me ...
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0 votes
0 answers
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Why doesn't an acid-base reaction occur in basic amide hydrolysis instead of nucleophilic acyl substitution?

In the reaction of Grignard reagent with a primary and secondary amide, nucleophilic acyl substiution doesn't happen. The reason given is that R- is a strong base as well as strong nucleophile, an ...
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-2 votes
0 answers
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Why doesn't Phenol follow the pattern for C-13 NMR?

I find this C-13 NMR Of phenol really weird. It's weird because I would have expected that $a$ would be the most shifted, then $b$, then $c$ and finally $d$. After all, d is the furthest from the ...
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2 votes
0 answers
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Can a hydroxyl group be attached to a triple bonded (sp hybridized) carbon?

Alcohols are defined as organic compounds containing one or more than one hydroxyl group attached to a sp3 hybridized carbon atom. And it is mentioned in the book I am referring to [errorless ...
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5 votes
2 answers
376 views

Can primary amine be produced using Grignard reagent?

I found a way to produce Secondary Alkyl Amines using Grignard Reagent. Ref: Z. Huang, J. Lv, Y. Jia, Chemistry Select 2016, 1, 5892. DOI: 10.1002/slct.201601464 But I want to know if I can use $\ce{...
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-2 votes
0 answers
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Does Cannizzaro reaction occur simultaneously during benzoin condensation?

Does Cannizzaro reaction occur simultaneously during benzoin condensation of benzaldehyde catalyzed by $\ce{NaOH}$ and thiamine? I assume that benzaldehyde break down to benzoic acid and benzyl ...
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2 votes
0 answers
75 views

Red P+HI with some specific functional groups

I've seen the related question (Does RedP+HI reduce all carbon functional groups to alkane?). Although the question is admittedly similar, neither the answer provided nor the document linked in it ...
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-1 votes
1 answer
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Why is the carbocation on the left more stable? [closed]

I assume resonance is coming into play here due to the hydroxy group on the carbon adjacent to the positive charge. What about the electron donating effect of the alkoxy groups?
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1 vote
0 answers
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How to get the total number of numbered positions in a molecule/compound

I'm working on a metabolite database where "labeled" compounds can contain isotopically labeled atoms in specific positions. When a new labeled compound is entered into the database, we'd ...
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