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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Priority to longest carbon chain or double bond? [duplicate]

Priority to longest carbon chain or double bond? Above structure and its nomenclature is given in my notes. However, I suspect it is wrong because the Carbon chain of 8 instead of 7 is available. So ...
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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 ...
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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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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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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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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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529 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
36 views

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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1answer
121 views

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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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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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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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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1answer
58 views

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

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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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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What is the line cutting benzene ring? [duplicate]

There is a line cutting benzene ring what is that called.
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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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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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35 views

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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1answer
34 views

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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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
56 views

Why is cyclopropane-1,1-diol stable [closed]

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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1answer
40 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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1answer
943 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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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
37 views

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
33 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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3answers
185 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
40 views

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

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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0answers
42 views

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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2answers
304 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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53 views

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 ...
3
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1answer
73 views

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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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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Methyl iodide in water

Iodide being a good leaving group and water being quite a weak $\ce{Nu-}$, does $\ce{CH3I}$ undergo $\mathrm{S_N1}$ reaction? I was taught that whenever a protic solvent which can ionize the halide ...
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1answer
52 views

DCC coupling of N-hydroxysuccinimide and Dimethoxy Acetic acid

I am forming N-hydroxysuccinimide ester: by DCC coupling with N-OH Succinimide and 2,2-Dimethoxy Acetic Acid. (Solvent: distilled THF). What I see on $\mathrm{^{1}H}$-NMR is 3 major singlets: $\...
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1answer
44 views

What is the mechanism of ring contraction of 6-bromo-7-methoxy-2,3,4,7-tetrahydrooxepine from seven to five?

I have recently come across a paper from here.I have tried to workout the mechanism for the following reaction presented in the paper. I was able to workout mechanism till acetal formation.It is a ...
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1answer
21 views

How do I calculate the proportion of respective conjugates of one base mixed with several acids (and/or conversely) at different temperatures? [closed]

How do I calculate the proportion of respective conjugates of one base mixed with several acids (and/or conversely) at different temperatures, and is there a free software tool that would allow me to ...
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2answers
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Reactivity of Grignard reagent

I had the following question at an exam: What is the fastest reacting compound towards nucleophilic addition with Grignard reagent? (a) Acyl chloride (b) Aldehyde (c) Ester It is ...
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2answers
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What is the major product of the reaction of a geminal dibromide with silver nitrate? [closed]

$\ce{Ag+/H2O}$ is used for peroxide formation, then followed by hydrolysis to yield an alcohol. But in the question it is a geminal dihalide and I don't know if the mechanism follows through a ...
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17 views

Effect of solvent on SN1 and SN2 reaction?

In SN1 reaction the increase in the polarity of the solution increases the rate of reaction. This can be explained by the increased solvation of the resultant ions and ease of ionisation. However in ...
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1answer
111 views

Di-alpha-halogenation of ketones in acidic medium

I was studying alpha-halogenation of ketones from LibreTexts Chemistry, Under acidic conditions the reaction occurs through the formation of an enol which then reacts with the halogen${^1}$. 1) ...
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1answer
37 views

Why should ether O be named as OXA in a bicyclo ring when it is a substituent?

I was asked to name the molecule below . For the following molecule, since ether is a substituent here (keto is more prior group) my answer was: 3-methoxy-6-methy-7-oxy bicyclo[2.2.1]hept-5-en-2-one ...
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1answer
50 views

FMO analysis of the [3,3] Sigmatropic reaction regarding geometry. Is it accurate?

While studying the reasons behind the stereospecificity of [3,3] Sigmatropic reactions, I ran into an image portraying both possible transition states for the reaction: The Chair TS and Boat TS. The ...
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29 views

How to rationalise the difference in reactivity between alcoholic and aqueous KOH with alkyl bromides? [duplicate]

Why is it that when we use alcoholic $\ce{KOH}$ with say $\ce{R-Br}$, E2 elimination occurs, whereas with aqueous $\ce{KOH}$, SN reaction takes place, as both have the same nucleophile, ie $\ce{OH^-}$?...
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What is the structure & hybridization in singlet and triplet nitrenes ..?

What is the structure & hybridization in singlet and triplet nitrenes .. some sources say triplet nitrene has sp hybridization with two p orbitals : http://burton.chem.ox.ac.uk/handout-2.pdf http:...
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1answer
59 views

How do I remove tetrabutylammonium perchlorate from an organic synthesis?

I am trying to remove tetrabutylammonium perchlorate (TBAP) from an organic synthesis where TBAP was used as an electrolyte. I am working with compounds containing the amide group. I have used flash ...
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1answer
131 views

Why is formyl chloride unstable while higher acyl chlorides are stable?

Source: Paula Bruice Ed. 2017 Pg.877 From this excerpt, we infer that formyl chloride is unstable. But how does that affect the reaction in any way? Is it just mentioned as a point to note or does it ...
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1answer
70 views

Why does Finkelstein reaction only work with R-Cl and NaI? [duplicate]

Why does Finkelstein reaction necessarily involve: R-Cl and NaI (in Acetone)? Why can it not be done with KI? How does potassium instead of Sodium affect the reaction? Why can't R-I react with KCl in ...
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1answer
103 views

What is proximity effect?

From page 780 in Organic chemistry, Seventh Edition by David R. Klein, I quote: "The 1,2-adduct is believed to form more rapidly as a result of a proximity effect. Specifically, the carbocation and ...