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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Action of sodium borodeuteride, hydrogen peroxide and hydroxide on propene

The question in the book states: What is the product formed when $\ce{NaBD4}$ and $\ce{H2O2}$/$\ce{OH-}$ react with propene The answer given is 2-deuteropropan-1-ol. My teacher said that there is a ...
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Proton NMR of tert-amyl alcohol

I just started learning about proton NMR. According to Molbase, the HNMR data for tert-amyl alcohol (2-methylbutan-1-ol) shows four kinds of protons at 0.9 ppm, 1.24 ppm, 1.44, and 3.65 ppm. However, ...
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1answer
44 views

Acid catalysed dehydration of alcohol with a bicyclo group

Pathway 1: Rate determining step is the formation of carbocation. In this pathway, a conjugated tertiary carbocation is generated as an intermediate. Pathway 2: One of the resonance form of ...
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monocholoroalkanes reaction with KOH [closed]

Alkane X has molecular formula C4H10. X reacts with Cl2 gas in the presence of sunlight to produce only two different monochloroalkanes C4H9Cl. both of these monochloroalkanes produce the same alkene ...
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Which compounds will react with HBr to give 1-bromo-1-methylcyclohexane? [closed]

Please help, mechanism or drawings are appreciated.
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163 views

Diastereomers or not

Why is the first one not a pair of diastereomers while the second is? The only reason I could think of was in the first $\ce{Me}$ is the same as $\ce{CH3}$ that is same groups even though differently ...
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1answer
24 views

Creating 100mg/L aspirin solution

I plan on creating 100 mL of 100mg/L aspirin solution by dissolving 10 mg of pure aspirin powder in 100 mL of buffer solution (of different pHs). Problematically, aspirin doesn’t tend towards ...
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1answer
63 views

Acid catalysed dehydration of 5-methylidenecyclopent-2-en-1-ol

I think the following reaction is NOT possible. I could not find a mechanism for ring expansion. Is ring expansion possible in any way? Is the following mechanism correct?
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Why don't phenol behave like aniline in electrophilic substitutions?

As far as I know, many electrophilic aromatic substitution reactions fail to undergo the usual way in aniline. This is due to $\ce{-H2N}$ group being basic (pKa of $\ce{NH3}$ = 38), even it is ...
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1answer
34 views

Acids used in Friedel-Crafts alkylation

I am learning adding alkyl groups to benzene using Fridel-Crafts alkylation: I know that it is very common to use $\ce{AlCl3/AlBr3}$ as Lewis acid catalyst in this reaction. But I am just wondering ...
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Organic Chemistry sulphonation [closed]

In sulphonation reaction chlorobenzene reacts with concentrated $\ce{H2SO4}$ in presence of heat To give chloro benzene sulfonic acid. Electrophile formed in this process is $\ce{HSO3+}$ which attacks ...
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Phenol vs 4-hydroxypyridine - Enol Content [duplicate]

Which has a higher enol content; phenol or 4-hydroxypyridine? The solution to this question in my book says that phenol has a higher enol content due to aromaticity. But 4-hydroxypyridine is also ...
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Enzyme Kinematics - Problem [closed]

Also, in the same reaction, if the initial velocity is V what is the final velocity.
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do isophyl alcohol wipes effectivness deteriorate in high heat

I have packages of alcohol wipes in my car and live in a very hot climate. Will the effectiveness (ability to kill virus, bacteria, etc) deteriorate? We are assuming packages will get closed between ...
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Resonance hybrid and octet

I am a student of grade 11. I am learning about resonance phenomena. I am a beginner with this and I am a bit confused about this. I wished to know whether atoms in resonance hybrid (not resonating ...
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1answer
64 views

activating and deactivating groups and directing effect

In electrophilic aromatic substitution: I have just learnt a 'rule' about benzene with more than 1 substituents attached (excluding the effect on steric hindrance): if a strong activating group (EDG) ...
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2answers
54 views

Dehydration of primary alcohol with a cyclobutadiene substituent [closed]

Note: Primary alcohol will follow E2 mechanism, therefore, removal of protonated water and proton (RDS) shall proceed in a single step in the above mechanism. My questions are: 1- According to ...
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1answer
46 views

Ozonolysis of alkene

(from Wikipedia) I am having trouble in the last step where the alkene ozonide is reduced to ketones / aldehydes specifically in the presence of water. My teacher is telling me that water will be ...
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23 views

Dipole moments of cis and gem alkenes [duplicate]

The procedure for comparing dipole moments for cis- and trans-alkenes is quite easy, but how to compare dipole moments of 1,1 dichloroethene (1); and cis-dichloroethene (2)? My teacher told me that ...
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Hydrogenation of Synthetic Motor Oil

I'm looking into adding hydrogen to my vehicle's air intake as a method of hybridization. Obviously, this could go badly for a number of reasons... But my primary question here is how could this ...
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2answers
48 views

Choise of solvent for extraction

In the synthesis of (S)-Diphenyl(pyrrolidine-2yl)methanol, I need to extract the product using an organic solvent and water. Which organic solvent is the most suitable in this case? Ethyl acetate: I ...
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Yield of possible products from acid catalysed hydration of an alkene with a phenyl group

Here, (b) is the major product due to formation of tertiary conjugated carbocation. My questions are: 1- Will a kinetically favoured (minor) product (c) form? 2- Is product (d) possible due to high ...
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1answer
106 views

Huckel's rule and aromaticity

I am learning to determine whether a monocyclic conjugated alkene is aromatic or anti-aromatic or not. question 1: cyclobutadiene: according to Huckel's rule, 4 * 1 = 4, it should be antiaromatic, ...
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1answer
158 views

Electrophilic substitution on Borazole

As Borazole ($\ce{B3N3H6}$) is aromatic, it shows electrophilic aromatic substitution. Now, my question is when borazole undergoes electrophilic aromatic substitution reaction, on which atom does the ...
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1answer
67 views

How to get or understand a sample in chemistry without knowing its chemical name or compound or formula [closed]

How to get or understand a sample in chemistry without knowing its chemical name or compound or formula? I was thinking about whether there is a way to understand what the chemical compound sample ...
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Lewis structure of R-COO-Na+ [closed]

I am studying Lewis structure and I have a question about an excercise. The question asks what is the Lewis structure of $\ce{R-COO^-Na+}$. I don't know how to draw it correctly.
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2answers
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Can I use calcium chloride instead of sodium sulfate as drying agent?

In the synthesis of N-ethoxycarbonyl L-proline methyl ester from L-proline and ethyl chloroformate, I dry the organic phase over sodium sulfate. Can I use calcium chloride instead of sodium sulfate? I ...
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1answer
90 views

Can I use potassium acetate instead of potassium carbonate?

In the synthesis of N-ethoxycarbonyl L-proline methyl ester from L-proline and ethyl chloroformate, I use $\ce{K2CO3}$ to neutralize $\ce{HCl}$. Can I use $\ce{CH3CO2K}$ instead of $\ce{K2CO3}$? I ...
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Poisoned catalysts

CaCO3 in rosenmund reduction, lead in Lindlar's catalyst, or steel in Raney nickel all act as poisins but the carbon in Pd/C is just for support. How do the others affect the catalytic activity but ...
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1answer
98 views

Pyridine synthesis by tin(II) chloride reduction of 5-nitronorbornene

What is the reaction mechanism here? I guess the $\ce{SnCl2}$ reduces $\ce{NO2}$ to $\ce{NH2}$ but then what happens?
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Effect of resonance on electron density in methyl vinyl ether

I am an 11th grade student. I am a bit confused in organic chemistry (General Organic Chemistry). I am unable to understand that whether oxygen wants to disperse its electron density or increase its ...
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What are the possible reactions between isopropyl alcohol(2-propanol), hydrochloric acid, magnesium, and tin(II) chloride(stannous chloride)?

Had an accidental discovery. Produced a mixture of hydrochloric acid in water (roughly azeotropic) with a moderate amount of tin(II) chloride dissolved within, then added several mL of that to 100mL ...
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chemically extract sodium from a food for health purposes [closed]

Spirulina is a consumable algae with some benefits and only one downside I have noticed. according to my research 2,300 mg of sodium a day is way too much. 10 OZ. of spirulina contains just under 3,...
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melting point of organic compounds [duplicate]

Why is the melting point of 1,4-dichloro benzene more than that of 1,2-dichloro benzene? According to me the latter has more dipole moment,so it should result in more molecular interactions and hence ...
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63 views

Is nitrogen a stereocenter in amides? [closed]

Consider $\ce{CH_3CONH-CH3}$. Is the amide nitrogen a stereocentre? I know 2 factors that can affect the chirality: amine inversion and resonance. I don't know if they apply here.
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Can anyone explain the reaction mechanism and products of Kolbe's electrolysis? [closed]

In my textbook it is written that Kolbe's electrolysis converts an alkyl acetate ion into an alkane, alkene and an ester, can anyone explain the mechanism behind this synthesis?
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45 views

Acid dehydration to ether

Can anyone please help me come up for a curved arrow mechanism for the reaction pictured? I'm familiar with the mechanism for the general acid catalyzed dehydration of butanol, where the arrow comes ...
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21 views

What is the meaning of pi selectivity?

I came across this term while going through a research paper for the first time of organic chemistry on diastereoselectivity of tricyclo[2.1.0.02,5]pentan-3-ones. I am not familiar with the term and ...
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2answers
50 views

Order of rate of acid catalysed dehydration of alcohols

The relative rate of acid catalysed dehydration of following alcohols would be: According to me, we have to arrange them in order of their carbocation stability. Q will be the most stable as it is ...
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1answer
124 views

Name of this bond-line formula? [closed]

I don’t know much about chemistry but I recently found the below bond-line structural formula painted on a wall near my place. I really can’t let go of trying to find the name of the compound. If ...
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2answers
37 views

Aspartic acid conjugate base acidity

Question Which hydrogen among the four in the conjugate base of aspartic acid is most acidic? Answer My attempt I am confused between Hb and Hc I know Hd has $\mathrm pK_\mathrm a \approx 9$, so ...
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Why does the solubility of haloalkanes in water decreases as the length of the carbon chain increases?

Due to the polar halogen-carbon bond in haloalkanes, they are more soluble than hydrocarbon in water. But the solubility is still very low because the overall influence of the dipole-dipole ...
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Isotope effect in sulphonation of benzene [closed]

Why does the reaction rate differ for sulphonation of $\ce{C6H6}$ and $\ce{C6D6}$? Why this difference is not seen in nitration or other electrophilic substitution reactions? Please explain the ...
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2answers
94 views

What is the mechanism for this intramolecular SN1 reaction?

What is the mechanism for the following intramolecular $\mathrm{S_N1}$ reaction? For this question, my professor hinted at an intramolecular reaction, and he asked us to recall the bromonium ion as ...
5
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3answers
346 views

Synthesing tetrahydropyran from ethylene oxide

I thought that the first step must be using a Grignard reagent to add carbons, but I need a hydroxyl group on the carbon on the other side to make it a diol and produce the product given, but nothing ...
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132 views

Oxidation using chromium trioxide [closed]

Oxidation of alcohol with $\ce{CrO3}$ I have come across different kinds of oxidation using ester formation (eg. Selenium/Osmium ester).This mechanism deals with the chromate ester. The structure of $...
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1answer
211 views

Why do electron-rich aryl groups have greater migratory aptitudes?

In the following reaction there are three possible aryl groups that can migrate: an unsubstituted phenyl group, a p-methoxyphenyl group, and a p-nitrophenyl group: Why does the electron-rich p-...
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1answer
155 views

Is hybridization of the cyclopropyl anion sp5?

I have read some answers about the $\mathrm{sp^5}$ hybridisation of carbon atoms in the $\ce{C-C}$ bond in cyclopropane as well as the $\sigma$-bond resonance in methylcyclopropyl cation. Overall, the ...
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1answer
72 views

Reaction of carboxylic acid with phosphorus trichloride

The reaction of carboxylic acid $\ce{RCOOH}$ with $\ce{PCl5}$/ $\ce{SOCl2}$ / $\ce{PCl3}$ yields an acyl chloride $\ce{RCOCl}$. With $\ce{PCl5}$ and $\ce{SOCl2}$ the reaction is quite simple utilizing ...
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Caffeine stability in cold water?

I'm wondering how long caffeine is stable in cold water (roughly). In fact, I like to make a jug of ice tea and keep it for up to a week in the fridge. I'm wondering if the caffeine breaks down over ...

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