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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residue after water filtered thru Brita and boiled [closed]

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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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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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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1answer
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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
36 views

Aromatic stability of pyrrole through resonance [closed]

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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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
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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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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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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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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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2answers
75 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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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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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 ...
3
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1answer
101 views

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
38 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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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
74 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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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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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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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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60 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
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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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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
119 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. ...
4
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1answer
60 views

Identifying the molecular structure of compound with sum formula C8H14O3 formula using NMR and IR spectrometry data

I am looking to identify the molecular structure of a compound with the sum formula $\ce{C8H14O3}$ using the NMR and IR spectrometry data below. I was able to figure out the molecule as My friend ...
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1answer
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How to name an alkyne with cyclic substituent?

My attempt: 1-(1-methylcyclopentyl)-3-methylpent-1-yne. Looks so messy though.
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1answer
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Ambiguity in naming haloalkanes

My question in quite simple why a compound such as chloro-ethane is called as such why is if not chloro-ethyl?? Since it is a hydrogen short.
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In aldehydes with an alkene substituent, what conditions favor Wolff–Kishner reduction over Clemmensen reduction?

This module I am answering asked me to provide a reason why Wolff–Kishner reduction is favored over Clemmensen reduction in reducing (3Z)-pent-3-enal to (2Z)-pent-2-ene but either Wolff–Kishner or ...
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1answer
45 views

Pyranose v/s Furanose form of Glucose and Fructose

According to my textbook (Class 12 NCERT Chemistry): Fructose also exists in two cyclic forms which are obtained by the addition of —OH at C5 to the C = O group. The ring, thus formed is a five ...
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21 views

Can cycloalkanes undergo electrophilic addition? If so, what is their mechanism?

Cycloalkanes have the same general formula as alkenes. Doesn't this mean that cycloalkanes can be saturated by turning into alkanes the same way alkenes use? If so, what is the reaction mechanism? In ...
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What are the compounds in oxygen and carbon dioxide indicator solutions that gives their color?

My brother had some leftover oxygen and carbon dioxide indicator solution for one of his take-home experiments from school, so he let me have them. I want to use them for an experiment and write out ...
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1answer
57 views

Safe to wash weighing paper?

I accidently washed the Fisherbrand weighing paper (cat. 0989812A) with acetonitrile : water (1:8) to remove some sample. The weighing paper appeared to deform a little bit after the wash. I wonder if ...
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2answers
50 views

Why are halogens base sensitive groups (Wolff-Kishner Reduction)?

So while studying about Wolff-Kishner reduction reaction to form alkanes from carbonyl groups. I read that it is not suitable for base sensitive groups as the environment is highly basic and as an ...
2
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27 views

Epoxide opening mechanism [duplicate]

Consider the following reaction: Our interest is the second step. Notice that after protonation of oxygen, the water molecule attacks in an S$_{\text{N}}2$ fashion. My question is, why does this ...
2
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1answer
35 views

Equilibrium with an E2 step

E2 mechanisms are known to be irreversible in general, because the forward step takes 2 species and produces three species, and a trimolecular reverse step is unlikely, purely on entropic grounds. (As ...
2
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1answer
47 views

Lack of elaboration in IR spectra of compounds

I've recently started learning about IR spectroscopy, and a common trend I'm seeing in my textbook and other sources is that not all the features in the IR spectrum are explained in detail. The focus ...
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36 views

I need to reduce the Nitrile group without affecting the boronic acid. How to do that?

I need to Reduce the Nitrile group (CN) in the (3-cyanophenyl)boronic acid in to a primary amine without disturbing the Boronic acid group.Using LAH can trigger reduction of Boronic group. what are my ...
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1answer
27 views

Comparing basic strengths between pyridine and 1,2-dihydropyrazine

Compare the basic strengths of above two compounds. In the first compound (1,2-dihydropyrazine), the lone pair of one N will participate in resonance but the lone pair of other N will not, similarly ...
2
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1answer
138 views

How can I synthesize 2‐amino‐3‐(chlorosulfonyl)benzoic acid from toluene or benzene?

I am trying to design a proper synthesis route for 2‐amino‐3‐(chlorosulfonyl)benzoic acid, though methyl 2‐amino‐3‐(chlorosulfonyl)benzoate—using an ester group in lieu of a carboxylic acid—would also ...
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1answer
287 views

Major product in dehydration of alcohol

Consider the dehydration of the following molecule with conc. $\ce{H2SO4}$ at $443 \text K$: The possible products are: The first one is the Zaitsev product and the second one Hofmann product. ...
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1answer
31 views

BPS & BPA treatment with 80% Ethanol

Background: BPA and BPS (Bisphenol A/S) are artificial estrogens and therefore toxic chemicals for us. They are used in the coating of thermal paper. Thermal paper is used to print in-store receipts. ...
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1answer
33 views

Stereochemistry + isomer check

We start with compound M: [Please imagine green bonds as dotted bonds going into the plane] From compound M, we are told that the 3 membered ring is opened u using sodium azide yielding a mix of ...
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1answer
29 views

How is o-Fluorophenol more acidic than phenol even after having Hydrogen bonding?

Source: Concepts of Organic Chemistry by Dr OP Tandon, Himanshu Pandey, Dr AK Virmani Page no: 241
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1answer
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Ring formation via oxymercuration-demercuration

I'm solving past problems from a 2014 Organic Chemistry II course (from a publicly available Harvard summer school Canvas page), when I came across this question: The answer (which is the reactant) ...
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62 views

How to find the moles of a salt added to a weak base, given ph

I would really appreciate some help with how to approach this: I'm given that: Methylamine (CH3NH2) is a weak base used in the manufacture of pesticides. Taking into account that the degree of ...