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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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
176 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
34 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
30 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
296 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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How do I go about calculating which of several carbonates would most easily decay when exposed to an acid?

For instance, I'd want to compare CaCO3, ZnCO3, MgCO3, etc and find out which one will decay with the least amount of an acid? Which laws / principles are involved that I'd need to find out how to ...
2
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0answers
36 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 ...
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1answer
52 views

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 ...
3
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1answer
65 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 ...
2
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2answers
42 views

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
28 views

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
44 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
40 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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0answers
46 views

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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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
39 views
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0answers
39 views

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
64 views

Reaction of geminal dibromide with silver nitrate [closed]

$\ce{Ag+/H2O}$ is used peroxide formation then followed by hydrolysis to yield alcohol. But in the question it is a geminal dihalide and I don't know if the mechanism follows through carbocation ...
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0answers
9 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 ...
2
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1answer
81 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
34 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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0answers
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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0answers
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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:...
3
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1answer
48 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 ...
5
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1answer
91 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 ...
0
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1answer
46 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 ...
4
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1answer
58 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 ...
4
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1answer
38 views

Are all fatty acids monocarboxylic acids?

This answer for this question might solve a multiple choice in my previous chemistry exam.(which caused an argument with my teacher) We know that fatty acids form fats and oil due to their carboxylic ...
0
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1answer
47 views

butane extraction (microbials)

I was wanting to know using a butane extraction method for hemp flower (cannabis sativa) would also extract the microbial DNA present on the flower as well as deriving the cannabis oil (oleoresin)? ...
11
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2answers
634 views

When 2-pentene reacts with HBr, what will be the major product?

If we consider the first step (formation of carbocation by the attack of the proton). A couple of textbooks I referred say that when the substituents on the $\ce{C=C}$ are different, the direction of ...
4
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1answer
27 views

Measure low DOM absorbance values in a microplate reader. Is there a suitable deep well microplate with flat bottoms available?

I would like to use a microplate reader to measure the absorbance of dissolved organic matter (DOM), but the measured values are close to the lower detection limit. To overcome this, I thought of deep ...
5
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1answer
44 views

Can I make a mirror on PET plastic using Tollen's reaction?

I want to make a very shiny surface, like a mirror. I tried to use chrome paint but it's barely shiny. It's more like gray even though I bought one of the most expensive crom looking paint. I know ...
2
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3answers
81 views

Visualizing rotation about a double bond

So I'm having trouble visualizing rotation about a double bond without using a model kit. The 2nd image has a red dot where I rotated it to make the molecule look exactly like the second image with my ...
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0answers
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Condensed Structural formula of 4,5-Dimethylhexane-1-ol

What is the condensed structural formula of 4,5-Dimethylhexane-1-ol? I'm confused between the following: CH(CH3)2CH(CH3)CH2CH2CH2OH CH(CH3)2CH(CH3)(CH2)3OH Doesn't the usage of parentheses around ...
0
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1answer
33 views

Why does this reaction produce an alcohol in one case and an alkene in the other?

Does it have something to do with the fact that the chlorine atom is bonded with the primary carbon, or with higher temperature in the upper reaction?
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2answers
63 views

How to convert wedge–dash structure into Fischer projection? [closed]

I am very confused when a compound with more than one chiral centre is given. How to find whether the two compounds are enantiomers or diasteromers? Please also explain how to convert more than one ...
0
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1answer
45 views

How to convert -OH to terminal -SH group in nucleolipids: [closed]

I am recently working on some synthesis of Nucleolipids and I want to transform $\ce{-OH}$ to terminal $\ce{S}$ group. Can anyone help?
3
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0answers
47 views

Rationale behind Barton's rules for catalytic hydrogenation

Organic Chemistry by Morrison and Boyd,Seventh Edition says - When cyclohexanones are used as substrates, the stereoselectivity of the reduction is found to be dependent on the acidity or the ...
2
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1answer
54 views

Why aren't there 2 products formed?

The question is asking for the major organic product. This seems like an $S_N1$ reaction to me as there is a weak base in $\ce{CH3OH}$ and heat. If it is, shouldn't there be 2 products. One with the $\...
1
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1answer
122 views

What is the total number of isomers, considering both structural and stereoisomers of cyclic ethers with the molecular formula C4H8O?

According to me, it should be 11 and this is how I have worked out as shown in the attached diagram. However, I am not sure whether all these 11 isomers can be considered as those belonging to ...
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1answer
38 views

Is 1,3 alkyl shift allowed in Cyclobutyldicyclopropylmethyl Cation?

While reading a post , i came across the following mechanism .(source : Which ring expansion in cyclobutyl(cyclopropyl)methanol is favourable?) The rearrangement is a series of shifts. The first ...
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1answer
55 views

What is the standard way to know the price of a chemical substance? [closed]

I've encountered many vendors with broadly varying prices for the same chemical substance, including amazon and Alibaba. I wonder if there is a standard way to know the universal/average price of a ...
4
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1answer
80 views

Qualitative Comparisons of Dielectric Constants of Organic Solvents

This question is inspired by the discussion around this earlier question. It is relatively simple to do a qualitative comparison of the polarities of different molecules (for example by analyzing the ...
4
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1answer
44 views

Identifying an extra NMR peak in silyl protection reaction

I protected a phenol with the TIPSCl/triethylamine procedure. The product was isolated by column (hexanes/EtOAc) and shows an extra singlet at 1.05 ppm in $\ce{CDCl3}$, integrating to ~10 H. Whatever ...
3
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4answers
66 views

Which ring expansion in cyclobutyl(cyclopropyl)methanol is favourable?

Predict major product: In this question first I've protonated the OH group and then water is removed to form a carbocation. Now I have to expand the ring, but I'm confused which ring to choose: ...
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1answer
43 views

Is this statement correct or not regarding SN1 reaction?

A primary alkyl halide may also undergo SN1 reaction in aqueous formic acid. This statement is written in one of my organic textbooks. Is it true ?
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0answers
28 views

On the stability of methyl mercury

Question: Given that $\ce{Zn, Hg}$ are in the same group, how to explain that $\ce{Hg(CH3)}$ is stable but $\ce{Zn(CH3)}$ is unstable and $\ce{Hg(CH3)Cl}$ is stable? $\ce{Hg(CH3)}$ seems to have an ...
2
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1answer
89 views

Synthesis of Aspirin, made unknown fluid

When I tried synthesising aspirin, after quenching and cooling it I noticed a translucent, milky, white fluid floating in the solution. The method used was: Salicylic acid (2 ml) was added to ...
2
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1answer
50 views

Preparation of sulfonyl chlorydes and mechanism of preparation of tosyl chloride

After searching about the preparation of sulfonyl chlorides, I couldn't find much. I found that for preparation of tosyl chloride, chlorosulfonic acid can be used, as in: Can chlorosulfonic acid be ...
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0answers
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Will (3R,4S,5R)-1,3,4,5,6-pentahydroxyhexan-2-one tautomerise in nitric acid?

The following question was sent to me .The question is " Which of the following is A ?" The given answer was a,b,c Background If both ends of an aldose chain are oxidized to carboxylic acids the ...