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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Why do we see complementary colors in UV/Vis Spectroscopy?

From what I read, a compound that absorbs visible light will produce a complementary color (using the color wheel), that can be seen. Why is this the case? Is it because, for example, if a molecule ...
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What is a non-empirical explantation of why 1-3 methyl shifts do not occur?

How could you explain why we never see 1-3 methyl shifts? Most sources just say it is really rare, but I was wondering if you could perhaps apply orbital selection rules or a frontier orbital argument....
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Reaction mechanism of 2-amino-4,6-dimethylpyrimidine as a nucleophile

My understanding tells me that 2-amino-4,6-dimethylpyrimidine can be deprotonated quite easily because the conjugated base is stabilized be resonance and act as nucleophile attacking aldehyde carbon. ...
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Why 2-Hydroxy benzene carbaldehyde steam volatile? [closed]

How to identify whether any compound is steam volatile or not?
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calculate the number of phases and components [closed]

Calculate the number of phases and components in the following systems: i). Dilute aqueous solution of H2SO4 ii). Saturated solution of ...
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1answer
78 views

How do I prepare the following compound from diphenylmethane?

I am having trouble with the preparation of this product from diphenylmethane as a starting material. One of my thoughts was to attach the butene into the structure, but I don't see how it is viable. ...
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How many resonance structures does the indene have after a deprotonation (indenyl)?

I have to explain why the cyclopentadiene is more acidic than the indene, and i have to draw their resonance structures after deprotonation of H+ of the indicated carbon (in the image below). I am ...
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What are the products of the following reactions? [closed]

I want to know what are the products of these reactions.
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2answers
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Is the elimination reaction between 1 1 dibromo cyclopropane and phenyl lithium feasible in alkaline medium (and some heat)

I found this question in one of my question papers for the JEE , My sir gave me an explanation that due to resonance between lone pairs of the bromide and π bond formed. This reasoning doesn't seem ...
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1answer
27 views

Why is baking soda good at dissolving grease? [closed]

Can someone please explain why baking soda is good at dissolving grease? Thanks,
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Looking for advice regarding a larger scale soxhlet extraction

I have successfully completed a few soxhlet extractions at a much smaller scale using a soxhlet extractor with ~200ml capacity. With that, I was able to extract from ~100g of pre-powdered, sonicated ...
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1answer
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I need help with Cahn-Ingold-Prelog (boat conformation)

I need to decide if the chiral carbon (with the attached hydrogen) is in R-configuration or S-configuration. To be able to do that, I need to know which of the atoms are pointing backward, forward and ...
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Non foaming, safe to handle surfactant [closed]

I'm looking to lower the surface tension of water in some flow experiments. Does anyone have a recommendation for a "safe" surfactant that is non-foaming and will reduce the surface tension to 20 or ...
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1answer
52 views

Why does H+ attack alkene first in this reaction?

The reaction is: Why is the double bond attacked here even though it is in conjugation with the lone pairs of O thereby making it harder to extract. Also,don't the 2 lone pairs on OH have more ...
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1answer
29 views

Cyclopentanone is treated with piperidine

cyclopentanone is treated with piperidine in acid catalyzed conditions to form the organic product (A). (A) on reaction with benzyl bromide followed by hydrolysis gives another organic product (B) ...
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2answers
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Solubility of Organic Compound confusion

My teacher wrote the following on the board today: A solute will only dissolve if the energy required to break the bonds in the solute and solvent is less than the energy released from the ...
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What are frustrated phases?

I was given a document on liquid crystals by my university , it does include subtopics on blue phases and twist grain boundary phases, but not much on frustrated phases.
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Is a glutathione conjugation a condensation reaction? [closed]

Glutathione conjugation is a reaction type used in detoxification of a lot of drugs.. I just wondered if it was a type of condensation reaction. Also, does a smal molecule have to be made in a ...
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Sn1 product for intermediates where positive charge is in conjugation [closed]

In case of carbocation intermediates where there are too many canonical forms possible which are not equivalent, where will the Nucleophile attack to form Sn1 product and why?
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How does a cyclization occur with a carboxylic acid and (CF3CO)2O?

The product of the reaction below is unsaturated, bicyclic ketone, but I'm confused as to how (CF3CO)2O reacts with it to cause the cyclization. There is no base involved so I don't know how the ...
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1answer
39 views

Which functional group contains two Carbon elements and one Oxygen element? [closed]

Which functional group contains two Carbon elements and one Oxygen element? The options are alcohols, esters, aldehydes, and ketones. When I try to research it, I'm not getting the answer I need at ...
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1answer
109 views

Preparation of p-chlorobenzoic acid from p-chloronitrobenzene

I was reading my book where I spotted the preparation of p-chlorobenzoic acid from p-chloronitrobenzene. The preparation method there was given as such: $\ce{Sn/HCl}$ $\ce{NaNO2 + HCl}$ ($\pu{0-5 ^\...
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Why basicity decreases for leaving groups, but nucleophicity increases for an overall compound, going down the periodic table?

Basically, I read that nucleophilicity increases going down the periodic table within a particular group, due to polarizability, but basicity decreases down a group (or family) in the periodic table, ...
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Will ipso substitution work in both cases of vanillic and isovanillic acids here or not?

What will be the product of the 2 reactions when bromine is taken in excess? I think ipso substitution will work here and there will be two $\ce{Br}$ substituting in both products, but in the ...
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How does resonance effect decrease the activation energy for the formation of carbocation intermediate in EAS? [closed]

This is a screenshot taken from my university's lecture note on EAS, which says: "... delocalizes the positive charge on the cation intermediate, lowers the activation energy for its formation..." ...
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1answer
57 views

Newman projections: how to tell which groups are bulkiest to determine what is the most stable conformation?

The scenario Let's say we have a molecule where in the Newman projection the front carbon has a hydrogen, methyl and an ethyl, and in the back carbon there's a hydrogen, something like a S, Cl or Br (...
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Why alkyl shift happens during hydroboration oxidation?

In this oxidation step, where alkyl shift happens for 3 times to kick out the OH- to obtain the boron-ester. But why does this happen? Won't the boron atom become less stable as the empty p orbital is ...
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1answer
36 views

For this molecule, can anyone explain why the nitrogens are sp2?

Here is the molecule - 4-Pyrimidone . I think the reason that the NH (next the ketone) is sp2 (normally, the three bonds attached to nitrogen, plus the lone pair would make it sp3) is because we don'...
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25 views

Why use OOH- instead of OH- to attack trialkylborane in hydroboration oxidation?

Boron in BR3 is still very electrophilic it has a empty p orbital. So I think any strong nucleophile can attack that, so I think of OH- that I added as it has a high concentration. However, what ...
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Which one of the following explanations is true for recrystallization technique? [closed]

We have organic chemistry lab quiz after three hours. We can not find the answers. Could you help our , please? The questions are below. Thanks in advance for your help.
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Oct 1ene on treatment with NANH2-DMSO isomerises to oct-2-ene [closed]

Oct -1-ene on treatment with NaNH2-DMSO isomersis to Oct-2-ene
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1answer
56 views

When we name an organic compound ,if there is double bond and a functional group which is now a substituent who has priority? [closed]

For example if a particular compound contains carboxylic acid, alcohol and double bond and the compound is such that we can either include double bond or alcohol in the main chain then who has ...
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Predict the product(s) formed in the following reaction and explain fully the reaction mechanism [closed]

Predict the product(s) formed in the following reaction and explain fully the reaction mechanism
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2answers
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What is the relationship between these isomers of dimethylcyclohexane (what type of isomers are they)?

What is the relationship between these isomers of dimethylcyclohexane (what type of isomers are they)? Is (1R,2S)‐1,2‐dimethylcyclohexane superimposable on its mirror image? What about (1R,2R)‐1,...
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How we can get product with more retention and less inversion of configuration? [closed]

Explain how you can get product with MORE RETENTION and less inversion of configuration, quote examples of both. Usually SN1 shows more inversion than retention.
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2answers
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Can Ethanol be used to carry out SN1 reaction?

My book says that the reaction of $$\ce{Cl-CH2-O-CH2-CH3}$$ with ethanol to form $$\ce{CH3-CH2-O-CH2-O-CH2-CH3}$$ occurs through $\mathrm{S_N1}$ mechanism, but shouldn't it actually be $\mathrm{S_N2}$...
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Why beta C w.r.t. the carbonyl group has the highest coefficient in the LUMO of acrolein?

I want to know the way, how to know which atom has greatest coefficient in a particular MO level in π-MO of a π conjugated system. I faced this problem when I was going through weak nucleophile attack ...
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24 views

Isopropyl Alcohol Vs Acetone for Dissolving Organic Contaminants on PCB

Acetone is widely used in the labs as a solvent to clean the vials and tubes as it is good solvent for organic materials. While Isopropyl alcohol is used as a rubbing alcohol for cleaning contaminants ...
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30 views

questions related to hydration of alkene with anti-markovnikov rule [closed]

I am a high school student and have just learnt hydration of alkene using (i) BH3/THF (ii) H2O2 + OH- + H2O from a reference book (organic chemistry 1st semester from Wiley), but got some problems (...
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2answers
233 views

m-CPBA Selectivity between Baeyer Villiger Oxidation and Epoxidation?

If both a ketone and an alkene are present in a molecule and you add one equivalent of m-CPBA, what are the factors that determine which group will be oxidized, the ketone through Baeyer-Villiger ...
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28 views

Reaction mechanism help [closed]

I need help with product. I tried to make anion and do carbanion shift, but it does not seem right as it does not seem to require "heat".
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how do you know if a Newman projection is chiral? [closed]

how do you know if a Newman projection is chiral? while converting it newman projection into sawhorse how do we know if the compound is chiral or Achiral
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What can we separate 3-methylcyclopentene and 4-methylcyclopentene by using ¹H NMR?

I write the structures and, I couldn't find any difference between 3-methylcyclopentene and 4-methylcyclopentene since all peaks are equal. Is there something I am missing?
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1answer
34 views

Electrophilic addition to benzene [closed]

A question deals with electrophilic addition to the following compound; Apparently, the benzylic carbon gets a positive charge during electromerism, invoking resonance stabilization. Benzene is an ...
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21 views

Effect of clemmensen reagent on 4-oxo-4-phenylbutanoic acid

When I first solved the question, I had reduced the ketonic group. Then as the medium is acidic the -OH in carboxylic acid, will get protonated and there will be formation of stable carbocation and it ...
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57 views

What are the functional groups present in (2S,5S)-2,5-dimethyl-1,4-dioxane?

How many types of functional groups are present in the given compound? (a) 6 (b) 5 (c) 4 (d) 7 I am not able to find functional groups in the given question. I thought of cyclic ...
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21 views

How do i determine R,S configuration for a pseudo-chiral carbon atom?

I recently saw a question on drawing meso forms of this compound. I understand that C4 is a pseudo chiral carbon atom because it is attached to two of the same groups. Then how do i determine the r,s ...
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46 views

E-Z system without a double bond

Can we apply E-Z nomenclature to geometrical isomers without a double bond. For example, can we use it for cis and trans isomers of 1,2-dimethylcyclohexane?
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1answer
28 views

Are the C1 and C3 carbons of cis 1-bromo-3-chloro-cyclobutane chiral?

I have tried to approach this from 2 directions: The ‘official’ method my textbook gives, which gives the correct answer - They are achiral It consists of going ‘priority-wise’ from the two carbons ...
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78 views

Is honey a good choice for chemistry senior essay? [closed]

I am doing my senior essay on chemistry and I was interested in honey, the only thing that's scaring me is that my content is more of biology rather than chemistry, in other words, does honey involve ...

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