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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7 views

Deciding which group twists out of the plane when ortho effect takes place

I'm going to take a few stills from 3D conformers of the following compounds available on PubChem in which ortho effect is applicable to show what I'm referring to. 2-Nitrobenzoic acid: N,N-Dimethyl-...
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-R and -I power at different positions in an organic compound

Why is the -R and -I power of a group minimum at para position whereas it is maximum at ortho position. For eg: In nitro benzyl carbocation, if nitro(acting as a -I as well as a -R group) is present ...
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R/S Configuration

Isomer A: I'm confused as to how I would assign priority to the carbon with the amine group attached. Does it matter if the highest priority group is facing into the page, would it have to be the ...
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What's the chemical reaction between NaOCl and Brilliant Blue dye?

Based on my research NaOCl dissociates into Na+ and OCl-. Looking at the photo, how does the OCl- ion and the brilliant blue dye structure end up as the product? How does the OH attach itself to the ...
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22 views

What is the difference between a quaternary center and a stereogenic center?

In other words, can a carbon with 4 substituents be quaternary but not stereogenic? For example, a carbon with an R1 group, an R2 group, and two R3 groups? Thank you!
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Regioselectivity of addition of hydracids to triple bond

Initially when a hydracid like HCl or HI is added to a triple bond it follows Markovnikov addition. However, when another molecule is addled to deplete the unsaturation, why does the addition follow ...
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Why is 1/100Conductivity,μs/cm=ion sum,meq/L? [closed]

Why is 100×anion(or cation)sum,meq/L=(0.9~1.1)EC,μs/cm? I get this equation from standard APHA-water analysis
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22 views

Borax + Citric acid =? [closed]

As far as I know sodium tetraborate dissolves in citric acid solution. What is the corresponding chemical equation?
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Calculate the number of moles of ethane, C2H6 , that can react with 12.2 moles of oxygen. Round your answer to the nearest hundredth [closed]

Calculate the number of moles of ethane, C2H6, that can react with 12.2 moles of oxygen. Round your answer to the nearest hundredth. pls help me I cant figure it out and I need it answered soon :( ...
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How do you name and number geminal molecules?

According to the current version of Nomenclature of Organic Chemistry – IUPAC Recommendations and Preferred Names 2013 (Blue Book), superscript arabic numbers are used to differentiate the nitrogen ...
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residue after water filtered thru Brita and boiled

Recently a number of residents in a condo tested & found the following:- (all utensils and cooking pots are washed and cleaned properly before testing) Tap water after filtered thru Brita, boiled ...
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23 views

What is the condensed formula for cyclohexane? [duplicate]

I can't find it written anywhere and my guess is that it doesn't exist as it would be impossible to write it out in a straight line. Could $\ce{CH2CH2CH2CH2CH2CH2}$ be used ?
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Please help 🥺 to name these compounds [closed]

Please 🥺 Help me . Name these compounds
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45 views

Checking chirality of a molecule [duplicate]

I know there are many symmetry elements like Plane of symmetry Centre of symmetry N fold axis of symmetry , but I am confused when will a molecule be chiral, if I say it should not posses any symmetry ...
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Frontier orbital analysis of zinc-catalysed carbonyl-ene reaction

Q1. Is the $\sigma_\ce{C-H}$ bond a donor in this reaction? If not, then can we take the alternate combination (HOMO of alkene, LUMO of the $\ce{C-H}$ bond and, HOMO of the carbonyl)? Q2. We can also ...
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Regioselective enolate formation, choosing major and minor products

This question came in my organic chem assignment. The options highlighted are the answers. The end carbon(adjacent to the carbonyl group) should have more acidic alpha-hydrogen and the alkene formed ...
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1answer
31 views

Aromatic stability of pyrrole through resonance

We know that the electronic configuration for nitrogen is $1s^22s^22p_{x}^12p_{y}^12p_{z}^1$. So whenever nitrogen has to form $3\sigma$ bonds it has to go for $sp^3$ hybridisation. So it will have 4 ...
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Fluralaner — how to neutralize? [closed]

My cat is experiencing some side effects from this FDA-approved compound: https://pubchem.ncbi.nlm.nih.gov/compound/Fluralaner#section=Related-Compounds-with-Annotation This has been in his system for ...
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24 views

Dihydropyran Protonation [closed]

Why is the cation always formed on the carbon near oxygen? I would think that O would have a -I effect and destabilize the cation. Or is the +M effect enough to stabilize it more than a methyl group?
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Chemistry hw Properties of Gases! [closed]

Solve the chart that says (Final description) must include the: factors that are changing, effects on pressure, constants)ty <3
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25 views

What is the proper use of the term “pi-donor ligand”?

Robert Crabtree's The Organometallic Chemistry of the Transition Metals (7e) describes a pi-donor ligand as being a pi-donor "as a result of the lone pairs that are left after one lone pair has ...
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1answer
37 views

EDTA sedimentation problem?

I tried to create a suspension of EDTA powder in Glycerin with 1:1 ratio. I keep facing problem of EDTA sedimentation. I've tried other ratios also but this was the only one which formed least amount ...
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19 views

N-hydroxysuccinimide as a good leaving group

In the synthesis of carboxylic acid derivatives (esters, amides), I often see N-hydroxysuccinimide used in conjunction with a coupling reagent (EDC, DCC). The reason given for this (from online) is ...
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What is the type of isomerism between 2,3-Dimethylhexane and 2-Methylheptane?

I understand that chain isomerism is when two molecules differ only by the classification of the carbonic chain, for example one being branched and the other straight, or one being open and the other ...
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23 views

Would the initial step of this mechanism be exothermic or endothermic? (Protonation)

My understanding is that since an O-H bond is being formed, the protonation step must be exothermic because energy is released upon bond formation. However, if I were to draw an energy/reaction ...
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38 views

How reliable is spectrometry in the determination of the oldest material Startdust?

After reading one of the latest findings by scientists, Stardust was considered the oldest material on earth. However having not much of an experience with chemistry, I was intrigued upon how ...
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What is a 'gamma' fatty acid? As in GLA, the essential omega-6 fatty acid?

I've learned about alpha, beta, and gamma and such in organic chemistry, but I cannot figure out what they mean in terms of fatty acids, like the alpha in ALA, etc. ....
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74 views

How is 4H‐1,4‐oxazocine aromatic?

I’ve found 4H‐1,4‐oxazocine in my chemistry book and I’m perplex as it states as aromatic: I can count 6 electrons on p orbitals which could satisfy Hückel’s $n = 1,$ but the oxygen is sp3-hybridized....
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28 views

Is there a reaction that can join two or more alkyl halides into an alkene?

How to acquire propanal from chloroethane while using only the substrate and any inorganic reagents? What's a two-step synthetic route to turn chloroethane into propanal? I can't use the Wurtz ...
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12 views

Why do primary halogenoalkanes react mainly by substitution, and secondary/tertiary by elimination? [closed]

I think it is because the nucleophile has less chance to react on the other R groups.
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Which is more reactive in E1, benzyl or allyl

I'm don't know the english terminology for chemistry so sorry for probably butchering some terms. My question is, which of these is more reactive in an E1 reaction: The bottom two are the ...
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Why are isomers of parathion less active acetylcholinesterase inhibitors than paraoxon?

Parathion itself has been found to be a very weak inhibitor of acetylcholinesterase. It normally requires metabolic activation and the conversion into paraoxon in the body to actually start exhibiting ...
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What is the role of imidazole in the Appel Reaction with iodine (I2)? Why are other bases not used?

I presume the role is to soak up the HI that is formed. Why not other bases such as triethylamine? Is this because the quaternary ammonium salt could be formed? Would other non-nucleophilic or ...
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1answer
37 views

Why does the pH of a weak acid not increase by 1 when diluted by a factor of 10? [closed]

Strong acid pH increases by one unit when diluted by a factor of 10, but why do weak acids not?
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18 views

Separate natural vanilla extract from ethanol [closed]

I have a extract of Tahitian vanilla in 35% ethanol that I would like to separate from the ethanol and transfer to a fixed oil such as fractionated coconut oil. Tahitian vanilla has some fairly ...
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26 views

Composition of gas emitted from Restaurant waste truck [closed]

I just got off the subway and the entire station was filled with an noxious odor such that people were gagging as they exited. When I got to the street, I saw a cooking oil recovery truck parked right ...
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1answer
73 views

Why is 11-oxabicyclo(4.4.1)undeca-1,3,5,7,9-pentaene aromatic?

I have been told by my instructors that for a compound to be aromatic, it must be planar. In this given molecule the oxygen seems to be out of the plane of the conjugated system: how can it still be ...
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25 views

Stability of Benzyl Carbanion [closed]

Out of these two Compounds which is more stable. I know that the Second Compound has -I effect , but without taking -I effect into account , I just wanted to know if Deactivating groups increase ...
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38 views

IUPAC Nomenclature for cyclic compounds without principal functional group [duplicate]

I am struggling naming cyclic compounds with multiple substituents and no principle functional group . If anyone can please elaborate the rules, it would be appreciated.
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12 views

Reasoning for as to which compound would undergo $\ce{S_{N} Ar}$ mechanism more quickly [duplicate]

Above are 2 compounds (p)-chloronitrobenzene and (p)-fluoronitrobenzene. So if both of the compounds were to undergo $\ce{S_{N}Ar}$ mechanism, according to me the (p)-fluoronitrobenzene should do it ...
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34 views

Changing terpenes [closed]

Hello and thank you upfront. I would like to create the ultimate legal (in Europe and USA for sure) cbd bubbel hashish. In order to give it the classic maroc smell and flavour, I will test with ...
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Mechanism of Hypervalent Iodine Phenolic Coupling

I need some help understanding the hypervalent iodine phenolic coupling reaction taking place in this synthesis of morphine, the reaction uses $\ce{PhI(OAc)2}$ as the hypervalent reagent and ...
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56 views

The nitrile isomers of C5H9N

I got the following 3 isomers of C5H9N correct: I also got the following fourth isomer (ignore the blue dot, it was a slip of the pen!) However, the given answers has the following 2 other isomers ...
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1answer
33 views

SN2 on compound containing halogen and carbonyl

I was given the following question on a sample exam for my organic chemistry course: I am quite certain that it would happen in a SN2-type reaction considering that the nucleophile is $\ce{CN-};$ ...
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1answer
50 views

Which is reduced to which? [closed]

In the reaction $$\ce{CH4 + 2 O2 -> CO2 + 2 H2O},$$ $\ce{O2}$ is reduced because oxidation state of $\ce{O}$ decreased from 0 in $\ce{O2}$ to -2 in $\ce{H2O}$ or 0 in $\ce{O2}$ to -2 in $\ce{CO2}$?
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1answer
15 views

%w/v question. Preparing 50 grams of Citrix acid 50%v/w solution [closed]

I’m reading a text that for preparing 50 grams of Citric acid 50% w/v solution, indicates to mix 25g of citric acid and 25g of water... To me, the 50% w/v in this case should be 50% w/w, right? The v ...
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26 views

Elimination vs reduction reactions - how to tell

Here are two compounds: Compound H: and compound I: Compound H reactions with the reagent shown below to form compound I and two other products. How would you clarify this reaction? I thought it was ...
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What functional & family group would heme as an organic compound be?

This is known as heme, it's part of hemoglobin. I'm confused as the image below has both multiple carbon ring chains, alcohol (OH), and a pi bonded oxygen. Is there a specific name for this or would ...
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3answers
115 views

Using a H NMR spectrum to determine the structure of a protein supplement

This question is about the H NMR spectrum of creatine. Creatine is a supplement taken by athletes to increase body mass. Recently, supplements containing derivatives of creatine have been marketed. ...

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