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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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Nitrobenzene - Aromatic Substitution Reactions

Which EAS (electrophilic aromatic substitution) reactions does nitrobenzene show? We know that nitrobenzene is particularly deactivated towards most such reactions, as the nitro group is strongly ...
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0answers
52 views

Why doesn't solvent form the major product in SN1 reactions?

If in a reaction SN1 pathway is followed then after the formation of carbocation the reagent or the solvent molecule can attack to form the product. As the number of solvent molecules are ...
5
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1answer
85 views

Cyclohexane derivative formation of carambolaflavone using a Lewis acid catalyst

The scheme below summarizes the results from a study into the optimum conditions needed for a key step in the synthesis of the proposed structure of carambolaflavone, a natural product that has ...
3
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0answers
31 views

PLGA - poly(lactic-co-glycolic acid) Synthesis

Does anyone have experience with the synthesis of PLGA? PLGA is synthesized by means of ring-opening co-polymerization of two different monomers, the cyclic dimers (1,4-dioxane-2,5-diones) of ...
3
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2answers
75 views

Can a reactor be operated at both reflux and above atmospheric pressure?

I'm not a chemist by trade so my experience in the lab has probably not been as in-depth as most of you. I've been tasked with investigating a proposed reaction in which an organic mixture (mostly ...
1
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2answers
42 views

Citric acid and ammonium nitrate

Soil based question. I have soil with to much Ammonium Nitrate in it. I am wondering if I use citric acid and water mixed will that flush out the extra Ammonium Nitrate that has built up in the soil. ...
2
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0answers
34 views

Protonation of pyridine

Recently, I have been reading the Nobel Lecture given by Kenichi Fukui when he won the Nobel Prize in 1981, for his contributions to the development of Frontier Molecular Orbital Theory. One of the ...
1
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0answers
28 views

Stability of Cycloalkyl Carbocations

What is the order of stability of the cycloalkyl carbocations? I think the stability should increase as we move from cyclopropyl carbocation to cyclohexyl carbocation, since the angle strain is ...
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0answers
41 views

To form 1-ethylcyclopentan-1-ol from Grignard reagent can we use 7-bromoheptan-3-one and 5-bromoheptanal as substrates?

Substrates to react with Mg to form Grignard reagent and then with hydronium ion to form alcohol. I just want to know that will reaction take place to form alcohol or side reactions will predominate ...
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1answer
86 views

What is the most common element in the human body? [closed]

I was wondering that since H2O was 66% of the human body, hydrogen would be the most. But apparently carbon is. Can someone explain that?
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1answer
54 views

Why only ketone forms enolate in Claisen condensation between ester and ketone?

Claisen condensation involves nucleophilic substitution in esters by an enolate (formed by removing an alpha-H from an ester or a ketone) giving a beta-keto ester or a diketone. My textbook says ...
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1answer
69 views

Naming ester as a substituent to carboxylic acid

Can carboxylic acid functional group -COOH and ester's functional group R-COO-R' be in one structure? If yes, carboxylic acid will be the parent chain and ester will be the substituent as c.a. is ...
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1answer
72 views

What is wrong in this reaction? [closed]

What is wrong in this reaction? I cannot find anything wrong, please help. Any hints would be appreciated.
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0answers
26 views

Substitution / Elimination competition

I am trying the hypothetical synthesis below, but I didn't get the product I was expecting. Instead, the reaction formed mostly styrene, in >80% yield (elimination product of the bromide) The ...
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2answers
39 views

Why does bromine water make the viscosity of olive oil increas? [duplicate]

Olive oil consists of almost 100% of fat. As you can see in the table of contents below, it includes both unsaturated, monounsaturated and polyunsaturated fats in the oil. Nutrition declaration per ...
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0answers
11 views

Adding an acetal to basic water

If you add an acetal to a solution containing water with a little bit of NaOH, will no reaction occur due to the stability of an acetal in the presence of a base?
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1answer
29 views

Why is a compound that is more stable gives out less energy upon reaction? [closed]

I am having trouble relating stability with energy released. For example, I am looking at a statement regarding Benzene that says, since delocalised electron model of Benzene is more stable than the ...
14
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1answer
733 views

For a benzene shown in a skeletal structure, what does a substituent to the center of the ring mean? [duplicate]

I have seen diagrams with both the substituents attached to the benzene ring by the edges and other occasions directly to the delocalized ring. What does signify?
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1answer
56 views

How do we know if this following molecule is a superimposable mirror image or non-superimposable mirror image ? [See Image attached]

How do we know if this following molecule is Super Imposable mirror image or Non Super Imposable mirror image ? [See Image attached]
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0answers
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How does HCl break down amylopectin in starch into amylose?

I'm currently researching on manufacturing bioplastics. During one of the steps, HCl is added to break down amylopectin into amylose, but I don't understand how exactly this happens. It would really ...
2
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1answer
30 views

How does hyperconjugation in alkenes affect bond lengths?

I understand how the diagram below results in hyperconjugation stabilising alkenes. Essentially, the C-H sigma bonding orbital interacts with the pi bonding orbitals creating two molecular orbitals. ...
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1answer
34 views

Efficient way to synthesize poly(alkyl)amine

I am trying to synthesize poly(ethylene-propylene)amine, i.e.: I've read that Reductive Amination is efficient regarding the reaction yield. However, it needs aldehydes to start the reaction. To make ...
0
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1answer
35 views

Can sodium hypochlorite soak all the way through an unglazed ceramic cup and bleach blue paper wrapped around the outside of the cup?

My question is regarding the ionic properties of sodium hypochlorite in house hold bleach. There is a debate among potters whether bleach will kill mold growing on a porous ceramic cup. It is my ...
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1answer
41 views

Doubt regarding timeline of events and development of theories

I recently studied Zaitsev's and Hoffman's rules for deciding which product is formed via elimination and noticed that the rules for formulated much before the discovery of electrons and any ...
4
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0answers
51 views

An unconventional decarboxylation to form bullatenone

I recently had an assessment which required me to draw the mechanism of decarboxylation of a $\beta$-ketoacid. However, it is slightly peculiar because there is the presence of $\alpha$, $\beta$-...
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2answers
563 views

Can a cyclic amine form an amide?

This is a question from the Cambridge International Examinations October/November 2017 (pdf from papers.gceguide.com, pdf via the Wayback Machine). I need to understand why the secondary amine in the ...
0
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1answer
29 views

Explain this boiling point order please [closed]

I read it from a book but don't know the reason. Please explain... Boiling point orders are - Ethanamide > Ethanoic Anhydride > Ethanoic Acid
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0answers
38 views

Can we use ( KBr + H2SO4 ) instead of (NaBr +H2SO4) in reaction with alcohol to generate alkyl bromide?

I have read somewhere that $\ce{H2SO4}$ is used to generate $\ce{HBr}$ and at other place it is written that it is there to protonate the hydroxyl group which fact should I believe ?
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0answers
24 views

Cyclic pent-diene + CHBr3 + t-BuOK. What is the product and how is it formed? [duplicate]

I think the answer is Bromo-Benzene but I am not sure. Please also provide the mechanism as to how the product is obtained.
1
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1answer
57 views

What will form when Dihalides or Trihalides or Polyhalides react with Magnesium?

I know that "R-X + Mg" gives RMgX. I want to ask if the Halide is Poly, then How's the formation of Grignard take place? For example. If 1,4 - Dibromobutane react with Mg, then what will be the ...
5
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3answers
572 views

Can solid acids and bases have pH values? If not, how are they classified as acids or bases?

This answer states $\mathrm{pH}$ is the aqueous concentration of $\ce{H3O+}$ or $\ce{H+}$ ions in soution. I would not say that ice lacks $\ce{H3O+}$ and $\ce{OH-}$ ions as ice's structure would ...
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0answers
15 views

Basicity of amides [duplicate]

Is benzamide more basic than acetamide? If it is ,why is that so?
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0answers
45 views

Is there a way to form only ortho product without using fractional distillation?

Using benzene and ethane as your only source of carbon in the final molecule, synthesize the following using any useful reagents. Reaction must form pure ortho compound. I have to form the ...
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1answer
40 views

Resonance effect of amide group

How will an amide group behave while being atrached to a benzene ring?Will it be donating due to lone pair of nitrogen or withdrawing due to carbonyl carbon?
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2answers
83 views

Cis trans isomer and cyclic compounds [closed]

8 Calcitriol is a steroid hormone found in human blood. Calcitriol shows geometrical isomerism. Give the number of geometrical isomers of calcitriol, including calcitriol. I’m confused I think it ...
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1answer
108 views

Planarity of given molecules in all conformations

Which of these have all its atoms in one plane in all the possible conformations (if any): A) buta-1,3-diene B) but-1-en-3-yne C) $\ce{CH2=C=O}$ D) $\ce{CH2=C=CH2}$ While I was ...
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0answers
48 views

Reaction of Br2/KOH with succinic anhydride

What products will be formed when $\ce{Br2/KOH}$ reacts with the following compound in water at room temperature? Here is what I think is possible: $\ce{OH-}$ will take up the acidic hydrogen. ...
4
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1answer
51 views

Role of NaI in Formation of Silyl Enol Ethers using Chloro(trimethyl)silane

I am forming silyl enol ethers using Chloro(trimethyl)silane (TMSCl), and below is an experimental protocol I am following Silyl Enol Ether Synthesis In an oven-dried 100 mL three-necked ...
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0answers
35 views

Does Raney nickel deprotect acetals?

I know that Raney nickel can deprotect thioacetals. Can it deprotect acetals as well? I found this image which shows that it deprotects and removes many protecting groups. But there was no reference ...
2
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1answer
43 views

Attack on cyclic intermediate during NGP

I have studied that when an epoxy ring opening takes place in acidic medium, the ring opens in a way that the most stable carbocation forms. This is due to the positive charge on the oxygen, which ...
2
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2answers
67 views

Why is it aqueous and ethanolic conditions for nucleophillc substitution of cyanide ion with benzyl chloride?

I was doing an exam question where benzyl chloride was undergoing a nucleophilic substitution with cyanide ion to form benzyl cyanide. Please can someone enlighten me as I have never seen both ...
1
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2answers
74 views

α-Halo ketone and strong base: Favorskii vs SN2 [closed]

Let us consider an α-halo ketone, with at least one α-H on the α carbon not containing the halogen. If I add a strong base, what is likely to happen: $\mathrm{S_N2}$ or Favorskii rearrangement? I ...
3
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0answers
69 views

Mechanism for the addition of chlorine to benzene to form hexachlorocyclohexane

I am familiar with electrophilic substitutions of benzene, with chlorine using a halogen carrier catalyst such as $\ce{AlCl3}$, to produce chlorobenzene, and I am aware of the mechanism. But, ...
0
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1answer
65 views

IUPAC nomenclature of organic compound

I strongly feel that the answer should be option (1) as the ester functional group has a greater preference over the double bond and hence it should get a lower locant. But the source of the question ...
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0answers
24 views

Why does energy need to be “compensated” in order for solvation to occur?

I am currently learning about the physical properties of alcohols. I understand that the main intermolecular forces between alcohols and water are hydrogen bonds. When these two are mixed, the ...
0
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1answer
55 views

Oxidation of 2-Methyl, 2-Phenyl Propane

Considering oxidation mechanism of side-chains in arenes, it is known that side-chains get oxidized to carboxylic group ($-COOH$). Below is a picture of 2-Methyl, 2-Phenyl Propane. When it gets ...
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1answer
44 views

What does it mean by 'the residue was taken up in solvent' in synthesis protocol?

The below is a synthetic protocol I need to perform: N-trifluoro acetoxy succinimide Synthesis Trifluoroacetic acid anhydride was added to N-hydroxysuccinimide at 0 °C. The reaction was ...
9
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1answer
237 views

Mechanism of the formation of peracetic acid

Wikipedia says that the equilibrium $$\ce{H2O2 + CH3COOH ⇌ CH3COOOH + H2O}$$ occurs. What is its mechanism? The following is my speculation. The first possibility is that $\ce{CH3COOH}$ is ...
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2answers
38 views

Comparing solutbility of acetanilide and diethyl ether in water

Would acetanilide be more soluble in water at 25 degrees Celsius because it has an $\ce{N-H}$ and an oxygen that can participate in hydrogen bonding, whereas diethyl ether only has an oxygen?
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1answer
37 views

Oxidation reaction of dimethylselenide / Selenourea with hydrogen peroxide

For my paper, I need to find the reaction between $\ce{(CH3)2Se2}$ and $\ce{H2O2}$ and between $\ce{SeC(NH2)2}$ and $\ce{H2O2}$. The mechanism below shows how I think it goes. The reaction should ...