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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Can molecular systems display negative magnetic susceptibility of a higher magnitude than bismuth?

Bismuth has the biggest value when it comes to a negative magnetic susceptibility than all other elements, ignoring superconductors, as they would have a value of -1. Yet, when tables displaying ...
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157 views

How come the methyl group (-CH3) is electron donating?

If the inductive effect operates purely through electronegativity differences, how come the methyl group is considered to donate electrons through the inductive effect? My textbook says that there is ...
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Why is the carbanion stability order the way it is? (3*<2*<1*)

According to the lecture notes I made, a 1* carbanion is more stable than a 3* carbanion. I can't grasp exactly why. (I had a look at the similar questions, the answers didn't help) With my very ...
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143 views

comparing acidity of oxonium cations ( conjugate acid of ketone, ether and alcohol)

I read that alcohol is the most basic among alcohol, ether, aldehyde and ketone. I am curious about the reason and I found the pKa of their conjugate acids: It makes me wonder: why is the ethanol ...
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263 views

Major product formed in Reimer-Tiemann reaction when Potassium Hydroxide is used as a base

Reimer-Tiemann reaction is known to give ortho major product when NaOH is used as a base. However there seems to be some confusion regarding the major product in case KOH is used as the base. It is ...
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60 views

Is the correct parent chain the longer one or the one including two double bonds?

I want to know which is the correct parent chain in this compound: Is it the one inside the loop, or the longer one that includes the part to the left of the allyl group? I know that once a ...
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69 views

Which is the correct parent chain in this compound?

In this compound: Will the parent chain be the one inside the loop, or the longer one including the single bonds to the left of the vinyl group? I know that carboxylic acid is the highest-priority ...
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1answer
86 views

Can dimethyl sulphide be used for ozonolysis of benzene?

There is literature that suggests that ozonolysis of benzene occurs with ozone and $\ce{Zn/H2O}$. Can it take place with ozone and dimethyl sulphide?
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Number of products formed in radical chlorination on a chiral center

If an organic compound with a chiral center of a specific (R) or (S) configuration, is chlorinated on that carbon center through a radical mechanism, will one product be formed or two? Basically will ...
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222 views

Reaction of cyclooctatetraene with sulfuric acid

Problem The correct statement is (A) P & Q are aromatic compound and Q has $\mathrm{sp^3}$-hybridized carbon atom. (B) P is aromatic with 10 π electrons and Q is aromatic with 2 π electrons. (C) ...
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Major product formed when 4-Methoxybenzil is reacted with a base

What will be the major product formed in the given reaction: I am not able to apply any of the reactions or mechanisms I know of in this case. The only thing I am able to predict is that the $\ce{OH-}...
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Why do different products form when alkali halide reacts with zinc in polar protic and aprotic solvents?

Let's take an alkali halide such as $\ce{CH3CH2Cl}$ the two reactions in polar protic and aprotic solvents are as follows: $$ \begin{align} \ce{CH3CH2Cl &->[Zn, CH3OH] CH3CH3}\tag{R1} \\ \ce{...
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Leakage during Celite filtration

I'm conducting a synthesis involving crown ether and Pd catalyst. In many papers, prior to column chromatography, they filter crude mixture through a Celite pad. I tried to, but leakage of Celite ...
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65 views

Effect of R/S configuration on reactions not involving the stereocentre

An exam question involved the following reaction - + forms Both reactants (2-methylbutanoic acid and 2-methylbutanamine) are optically active. The question used pure R-enantiomer of the acid, and a ...
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Translating from milligrams in the pill to Ki at the receptor

Many places (e.g. Wikipedia) report the action of a drug on the various receptors, transporters, ion channels, and the like in terms of the Ki(nM). (This is for drugs that act primarily through such ...
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Possibility of further chlorination of hexachlorocyclohexane

The reaction of benzene with excess of chlorine in the presence of sunlight produces 1,2,3,4,5,6-hexachlorocyclohexane as the major product. This is also given in the preparation section of the ...
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Why is the enthalpy of formation of 2,2-dimethylpentane larger than that of 2,2,3-trimethylbutane?

Firstly, it is commonly known and taught that branched alkanes are more stable than linear ones, and so have larger enthalpies of formation. But why is that the case? Are there some steric ...
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46 views

Can exact bond angles in cycloalkanes be calculated?

I know that bond angles in cycloalkanes are usually different from $\ce{109.5}^{\circ}$ as predicted by the VSEPR theory because of their shape, and a higher deviation will cause a higher ring strain. ...
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2answers
181 views

Decarboxylation of primary amino acids

Since primary amino acids like glycine, alanine can't be decarboxylated under oxidative conditions, what would be the best catalyst for this reaction? I was thinking about copying decarboxylases with $...
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1answer
78 views

Reduction of nitrobenzen using LiAlH4 [closed]

Can you please explain why isn't nitrobenzene reduced to aniline but turns out as azobenzene on reaction with LiAlH4? Please explain the mechanism.
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1answer
159 views

Formation of enamine for unsymmetrical cyclohexanone derivatives

Question: Answer given: D My answer: C My reasoning - I outlined the following steps in the reaction: Nucleophilic attack of pyrrolidine on the carbonyl, leading to the carbon atom now having one $\...
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84 views

Reaction mechanism of formation of salicylic acid with Phenol and carbon tetrachloride in basic medium?

With classic Reimer-Tiemann reaction a variation is also given in my lecture notes which use carbon tetrachloride instead of chloroform. But to me, it seems like it would be just a substitution ...
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50 views

Does the nucleophilic substitution in an acid chloride always proceed through a tetrahedral intermediate?

I am a beginner in organic chemistry and would like to ask for the mechanism for the nucleophilic substitution of carbonyl groups from acid chloride - especially regarding the tetrahedral intermediate?...
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1answer
86 views

Double bond or carbanion for nucleophillic attack [closed]

I came across this question: According to me the Hydride ion should take hydrogen from left (unsubstituted carbon) because carbanion will be more stable there and this carbanion will then act as a ...
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69 views

Driving force in Corey-House reaction

In my textbook of organic chemistry by francis carey 11th edition, the Corey-house synthesis is elaborated on in the topic of organocopper reagents. It is mentioned that as the R-X alkyl halide is ...
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37 views

How do molecules with opposite rotational photoisomerization bonds behave? [closed]

If a molecules bond change upon isomerization with the respective bonds straining the molecules as they orient themselves opposite from each other, would the molecule undergo some kind of ...
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Advantages of p-toluenesulfonic acid over sulfuric acid in the formation of acetals

I am currently working on an undergraduate experiment to form a cyclic acetal. We were asked to use p-toluenesulfonic acid as a catalyst rather than sulfuric acid. This seems to be common practice ...
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60 views

Claisen condensation of methyl benzoate and ethyl propionate

I am planning to preform the Claisen condensation between a benzoate ester (methyl benzoate is the only one I can get) and a propionate ester (ethyl propionate is my only option). The idea is to ...
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31 views

How to know what lubricant is compatible with resin matrix

I am reading a lot of papers on electrically conductive adhesives that say that the filler (flake) is coated with lubricant which needs to be “compatible” with the epoxy resin matrix to have good ...
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69 views

Does amide ion prefers to act as a base than a nucleophile?

In this question, I think that amide ion, being a good nucleophile should attack on the terminal carbon through $\mathrm{S_N2}$ mechanism to form compound (c), but the answer given is (b), and the ...
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1answer
99 views

Does Ei or pyrolytic elimination reaction undergo carbocation rearrangement?

I've read about E1 reaction (unimolecular elimination reaction) which forms the most stable carbocation first and then undergoes the elimination. Ei is also mentioned to be "unimolecular" in ...
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50 views

Nitration of haloarene

Question: Convert benzene to 4-bromonitrobenzene. My attempt: Answer given: Is my solution correct? Can aryl halodes react directly with $\ce{AgNO2}$ to form aryl nitrate?
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226 views

Miscibility gap of heptane-methanol mixture

To explain my question a bit better: I added heptane and methanol together in equal ratios (1:1) and observed a separation in phase where there appeared to be an oily layer sitting on top of the other ...
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1answer
77 views

Dehydration reaction of an alcohol, 2,3-dimethyl-2-phenylbutan-1-ol, with conc. sulfuric acid (at high temperature)

What's the major product of the dehydration reaction of 2,3-dimethyl-2-phenylbutan-1-ol with conc. $\ce{H2SO4}$ (at high temperature)? I am aware that in this reaction $\mathrm{E}$1 mechanism will be ...
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40 views

Does lithium aluminium hydride react with conjugated dienes? [closed]

I have searched many websites, but was unable to find if $\ce{LiAlH4}$ is able to reduce conjugated dienes, such as styrene to ethylbenzene or 1,3-butadiene to 1-butene.
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2answers
89 views

How do you achieve phase separation of a methanol / chloroform solution?

If I'm washing a methanol solution with chloroform, can I just add water in a 1:1 mixture with the methanol and expect it to break? Do I need to do anything else to cause the aqueous phase to separate ...
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1answer
98 views

Why does Br2 brominate CH4 over CH3Br?

I was reading about the bromination of CH4, and saw that since Br is "selective" in its bromination, when you brominate CH4 with Br2 you predominately get CH3Br, and not CH2Br2. What about ...
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49 views

How are cyclodextrins used to form inclusion complexes with drug molecules?

I'm talking about practical application. A cyclodextrin molecule hosts a drug molecule inside of it in order to increase solubility and stability of the drug. But how do we make sure this inclusion ...
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1answer
213 views

What is the isomeric relation between bicyclo and spiro hydrocarbons?

Take for example octahydropentalene (bicyclo[3,3,0]octane) and spiro(3.4)octane: I would think that they are chain isomers of sort but according to nomenclature counting rules, they are both 8-carbon ...
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39 views

Hydrogen as a reference in inductive effect

What does it mean when we say that I-effect of hydrogen is taken as zero ? I think that it means that partial displacement of sigma bond electrons between two atoms of different electronegativity is ...
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101 views

Is there any specific conditions for Neighbouring group participation?

I got to know about what neighboring group participation is, but does it always occur if there are lone pair donating groups in beta or delta positions. Or does it only occur in some kind of medium or ...
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45 views

Why is 4-hydroxyacetophenone more acidic than 3-hydroxyacetophenone? [closed]

At 25 °C, the $\mathrm{p}K_\mathrm{a}$ of 3-hydroxyacetophenone is 9.19, while the $\mathrm{p}K_\mathrm{a}$ of 4-hydroxyacetophenone at the same temperature is 8.05. Why is that so? 3-...
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1answer
46 views

Alkyl halide nomenclature, flouthane [duplicate]

The IUPAC name for flouthane is 2-bromo-2-chloro-1,1,1-triflouroethane. i am confused why did not we assign the numbering to the carbon chain the other way possible that would make the name as 1-bromo-...
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68 views

Can a Grignard reagent form magnesium halide with an alkyl halide? [duplicate]

$$\ce{RMgX + R'X' -> RR' + MgXX'}$$ Is this reaction possible? I am not able find any reference to it in the books that I have. Anyone has a reference?
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Why do poisoned catalysts (Lindlar, nickel borate) result in partial hydrogenation of alkynes?

I read that alkene is more reactive than alkyne, so in hydrogenation of alkynes, it's difficult to isolate the alkenes. But with poisoned catalysts like Lindlar's catalyst or Nickel-Boron (Ni2B), they ...
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1answer
60 views

How would I go about developing a linker molecule that binds SiO2?

I'm trying to develop a molecule that acts as a bridge between a protein and surface of SiO2 lattice. The end that binds the protein is simple and easy but I can't figure out a way to draft up how I ...
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39 views

Textbook on Food Additives? [closed]

My Question. Is there a comprehensive textbook on (synthetic) food additives? Many textbooks on nutrition omits any discussion of food additives, so I was hoping there is a book devoted to the subject....
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1answer
180 views

Why don't we consider the attached hydrogens in inductive effect?

Consider the molecule 1-chloroethane Let carbon attached to $\ce{Cl}$ be $\ce{C1}$ and other one be $\ce{C2}$. While learning inductive effect I was told that $\ce{Cl}$ due to high electronegativity ...
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68 views

Why is an allyloxycarbonyl (Alloc) protection group more acid-stable than tert-butyloxycarbonyl (Boc) protecting group?

Why will Boc get cleaved under acidic conditions while Alloc does not? Can Alloc somehow be resonance stabilized? If so, how? Any help would be appreciated.
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1answer
242 views

Electrophillic susbtitution of bromine on styrene and cinnamic acid in the presence of FeBr3, a Lewis acid

Bromine gas, in the presence of $\ce{CCl4}$, undergoes on addition reaction at the double bond in both styrene and cinnamic acid, illustrated below. Styrene: Cinnamic acid: Bromination of benzene in ...

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