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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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Comparing the emission spectrum of ethanol and mixture of alcohols

Sorry if this question has a simple answer but I've been unable to find it elsewhere. Using a diffraction grating, burning ethanol (99.9%) will produce a rainbow of colours. However, when burning a ...
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0answers
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Polar Protic and Aprotic Solvents

I know $\mathrm{S_N2}$ is favored polar aprotic solvents, which means that they may have hydrogens on them somewhere, but they lack $\ce{O-H}$ or $\ce{N-H}$ bonds, and therefore cannot hydrogen bond ...
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3answers
392 views

Why does using NaI as a nucleophile and acetone as solvent lead to an SN2 reaction mechanism instead of SN1? Is I- not considered a weak nucleophile?

In a reaction with a secondary leaving group, why does using $\ce{NaI}$ with acetone as a solvent lead to an $\mathrm{S_N2}$ reaction mechanism instead of $\mathrm{S_N1}$? I thought that halogens were ...
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Can a strong base (in this case Sodium Hydroxide) be effectively weakened ie: safe without the neutralization of it? [on hold]

I wish to figure out If I can retain Sodium Hydroxides ability to hydrolyze fats yet allow it to be safe to humans. I was curious if it were possible without the neutralization of the base.
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Rate of reaction of halogens in a substitution reaction

When a substitution reaction takes place in a substrate having halogen, Why is it that iodine reacts the fastest and fluoride is the slowest ? For sure the iodine has a weaker bond but it is also ...
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Iodide via SN1 in anhydrous medium

In anhydrous medium fluoride ion is the strongest nucleophile whereas iodide is the weakest. I was wondering if in anhydrous conditions, SN1 reaction with an iodide could take place. I have been ...
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2answers
506 views

Coupling of silyl imine and aldehyde

LDA is a strong base and probably deprotonates somewhere which I'm not sure about. It I would to make a guess it would probably be beta to the imine. This is following by nucleophilic attack of the ...
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1answer
602 views

Which singlet dihalocarbene has the strongest carbon-halogen bond?

There are three singlet carbenes - difluorocarbene, dichlorocarbene and dibromocarbene. Which has the strongest carbon halogen bond? Obviously backbonding is a point to be considered, as carbene is ...
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What is the mechanism of the reaction of ethyl prop-2-ynoate to ethyl (2Z)-2,3-dibromoprop-2-enoate?

It's really weird for the product is 99% Z-comformation? Please tell me why? This reaction can be found in scifinder.
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1answer
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Addition of aqueous KOH to 3-bromobut-1-ene

On addition of aq $\ce{KOH}$ to 3-bromobut-1-ene, substitution reaction should take place via $S_N1$ mechanism but in this an allylic carbocation forms which could rearrange. In that case which ...
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2answers
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What reagents or series of reactions would allow for selective hydroxylation of an allylic methyl group outside of a ring?

Sample transformation for selective hydroxylation of an allylic methyl group outside of a ring. Selenium dioxide would not work since hydroxylation would be favored inside the ring.
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1answer
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How would one carboxylate CBG into its acid form, CBGA?

I have a project that would require cannabigerolic acid (CBGA) as a synthase substrate, but the only available chemical I can find is cannabigerol (CBG). CBG is the product of CBGA through ...
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Mechanism of DPD (N,N-diethyl-p-phenylenediamine) reaction with free chlorine

NOTE: As I've been finding new informations about the question, I've been editing the question to keep it up to date. If some comment doesn't make sense just check the Edit History. DPD (N,N-diethyl-...
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2answers
38 views

Which reaction is useful to prepare odd number of hydrocarbons?

Which reaction is useful to prepare odd number of hydrocarbons: Wurtz reaction Kolbe electrolysis Corey–House synthesis Oxymercuration Wurtz reaction produces even products except if we take ...
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1answer
72 views

Kb values of N,N-dimethylaniline derivatives [closed]

I need the $K_\mathrm{b}$ values for ortho-, meta- and para- positions of the following compounds: I've looked and couldn't find them anywhere.
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Will 1-[2-(chloromethyl)phenyl]propan-2-one, follow a Williamson ether synthesis route or, a Diels-Alder reaction?

I was asked to find the product of potassium ethoxide reaction with 1-[2-(chloromethyl)phenyl]propan-2-one (1). I came up with two different paths, each leading to the same product. 1-[2-(...
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1answer
44 views

How does 1-bromo-2-fluorobenzene react with lithium amalgam? [on hold]

How does this organometallic reagent react with 1-bromo-2-fluorobenzene? Does it react like Grignard reagent? If the product of this reaction is then reacted with furan, what will be the final product?...
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2answers
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How are neutral amines effective bases in organic chemistry?

I have found it to be rather strange that neutral amines, such as triethylamine or DIPEA, find applications in organic chemistry in deprotonating alcohols or even α-carbonyl compounds. Amines are ...
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0answers
28 views

Addition v/s elimination with double bond and OH together

If a compound has both an hydroxyl group and a double bond and we add $\ce{HBr}$ to it, (a) substitution reaction to the hydroxyl group can take place, or (b) an addition reaction of a ...
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0answers
22 views

heat of hydrogenation, putting the molecules into a right order [on hold]

could anyone help me with this question out?: I should put the molecules in a rising order in terms of the heat of hydrogenation. 1-Butene, (E)-2-Butene, 2-Methyle-2-Butene, 1,3 Butadiene,(Z)-2-...
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What is the line cutting benzene ring? [duplicate]

There is a line cutting benzene ring what is that called.
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0answers
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Hydrolysis of an amidine derivative under acidic conditions

I know that an imine can undergo acid hydrolysis to yield a corresponding amide: https://chem.libretexts.org/@api/deki/files/13283/10.jpg?revision=1 But I am looking at a mechanism for acid ...
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0answers
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Controlled chlorination of methyl group of toluene

I've seen a reaction in which tolune is converted to chloromethyl benzene and another to dichloromethyl benzene, both with the conditions Cl2, PCl5. If this is a radical mechanism, could you control ...
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1answer
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Synthesis for turning synephrenine into N-methylphenethylamine

I am trying to devise a synthesis to change synephrine (4-[1-hydroxy-2-(methylamino)ethyl]phenol) into N-methylphenethylamine. I was figuring that I could remove the hydroxyl group attached to the ...
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1answer
881 views

How long would it take for sucrose to undergo hydrolysis in boiling water?

I was reading the book Cocktail Codex and there was a snippet on avoiding boiling sugar and water to make simple syrup that made me a bit skeptical. Here it is: Heat also affects the molecular ...
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1answer
24 views

What Are Examples of Reducing Sugar in Mailliard Reaction?

I'm interested in food science, and I've been reading about Maillard reaction. All of the articles / videos about Maillard reactions that I found online mention that reducing sugar and amino acids ...
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0answers
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How to synthesize (4-chloro-2-methylphenoxy)acetic acid from 2-methylphenol? [on hold]

How to synthesize (4-chloro-2-methylphenoxy)acetic acid (mPCA) from 2-methylphenol?
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0answers
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What are the chemical principles behind paper/ink deterioration over time and how do I prevent them? [duplicate]

I have been working on a time capsule for the past few months, in which I decided to not include any electronics (ie: no USB). I am done writing the content of the capsule, but I have some concerns ...
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1answer
9k views

Nomenclature of organic compounds containing complex side chains

How do we decide the sequence of substituents in a organic compound if one of the substituents is complex. Should the complex chain must always be written first while writing the IUPAC name or are ...
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3answers
170 views

Shouldn't it take more energy to break CO2 compared to CO? [closed]

I read in a book that bond dissociation energy of carbon monoxide $(\ce{CO})$ is $\pu{749 kJ/mol}$ and carbon dioxide $(\ce{CO2})$ is $\pu{532 kJ/mol}.$ Shouldn't it take twice as much energy to break ...
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1answer
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Epoxidation with peroxyacids

In this particular epoxidation/hydroxylation reaction, why does the epoxide only form at one of the double bonds and not both? The compound initially reacts with the peroxyacid to form an epoxide, ...
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1answer
38 views

Why is cyclopropane-1,1-diol stable [on hold]

The reason given me in my book is that it's stable due to steric relief. The answer given on quora said "there is a lot of angle strain." What exactly is steric relief ? Can anyone help me elaborate ...
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0answers
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Intermolecular force (Chemistry-structure and properties of matter) [on hold]

Some trees grow larger at unusual height. Predict why not all trees can achieve unusual heights?
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2answers
20k views

What is the priority for numbering alkyl side chains?

I'm wondering why the above image is named 5-ethyl-3,3-dimethylheptane rather than 3-ethyl-5,5-dimethylheptane. I thought an ethyl substituent has a higher priority (I know this is true when arranging ...
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1answer
27 views

Things to consider to determine stability of a compound to another? [duplicate]

Some Compounds with higher bond dissociation energy seem to be more reactive towards certain compounds then ones with lower bond dissociation energy , so what are the things you need to factor in to ...
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0answers
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Aldol Reaction on an intermediate

I was given the following reaction to prove a mechanism for: and I managed to prove the first step with ease. The second step, forming the "base-catalysed aldol" is the part that's rather confusing ...
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1answer
31 views

Priority of carbons attached to chiral group, one with double bonded oxygen, one with two oxygens [on hold]

I have a chiral carbon. Two of the atoms attached to the carbon are other carbon atoms. One of those carbons has a double bonded oxygen and a methyl group attached. The other has two oxygens and a ...
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1answer
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Grignard alkene on a carbonyl

I was given the following mechanism to prove today post-lecture: and my attempt is given below. Now, when the negative charge on the alkene attacks the carbonyl, the electrons are pushed onto the ...
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2answers
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Why do larger alkyl groups show a greater inductive (+I) effect?

I have been taught that an alkyl group shows a +I (positive inductive) effect. Why do they do so? I know that hyperconjugation can explain how alkyl groups could stabilize a carbocation (better than a ...
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2answers
292 views

Tiffeneau–Demjanov rearrangement products

With reference to the paper McCasland, G. E. Pinacolic Rearrangements of Epimeric Aminocyclanols. J. Am. Chem. Soc. 1951, 73 (5), 2293–2295 DOI: 10.1021/ja01149a110. (ResearchGate link). It states ...
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0answers
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Resonance forms of deprotonated hydroquinone

What resonance forms stabilize deprotonated hydroquinone? Deprotonated hydroquinone looks like this: Possible resonance forms include: 1 and 2 look reasonable: they don't carry multiple charges. My ...
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0answers
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How hyperconjugation possible in the below carbocation [closed]

![enter image description here](https://i.sHow hyperconjugation possible in this carbocation
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1answer
383 views

Isocyanides undergo addition reactions, but cyanides do not. Why?

My book mentions addition reactions of isocyanides with halogens, ozone, sulphur, etc. but it doesn't mention any such reaction for cyanides. Instead, it bluntly states: "Cyanides do not undergo ...
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0answers
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Robinson annulation

In the mechanism of Robinson annulation, what is the rate determining step? I have searched in my book but it is not given. If possible please specify the reason for that step being the RDS. Thanks in ...
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0answers
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Dibromoethane Symbol Equation [closed]

Can Dibromoethane (CH2BrCH2Br) be written as 2(CH2Br)? I'm doing GCSEs so I have no idea about stuff like this. Thanks!
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0answers
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Preserving a DMSO “tincture” of plant extracted compounds [closed]

I have soaked dried plant material in 99.99% pure DMSO for compounds extraction. I have then filtrated the solution. DMSO is hygroscopic, which means it will induce water over time. Q1- How long ...
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2answers
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Number of geometrical isomers when a cyclic ring is involved along with axis of symmetry

This is an question from my Chemistry study material and it asks to find the number of Geometrical Isomers of the following compound in the picture. Basically the method/formula given in my book to ...
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1answer
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Ethanol is added to chloroform bottle

I was doing MCQ and the question asked was ethanol is added to chloroform bottles. I know chloroform it gets converted to phosgene gas (which is poisonous gas in presence of air and light ). to ...
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0answers
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What Chemical Compounds Combust when Burning Coal & What is Coal Made of

My research suggests that when burning Coal to produce energy (or just burning coal in general), Carbon Dioxide is released into the other along with other gaseous chemicals. What other chemicals ...
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0answers
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Why is ozonolysis of benzene possible?

I was looking at a question which asked to predict the product of reductive ozonolysis of benzene using $\ce{Zn/O3/H2O2}$ and I predicted them correctly using the cleaving of the double bond shortcut ...