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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2answers
88 views

Finding major product after dehydration

here,should I prefer hydride shift or a product with more $\alpha$ hydrogens? my doubt is...as hydride shift is easier than methyl shift,the answer should be $a$ or $c$.if methyl shift takes place the ...
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1answer
30 views

Synthesis of 1-naphthaleneacetic acid: Methods

I am trying to synthesizing 1-naphthaleneacetic acid from naphthalene and monochloroacetic acid. I found some patents and papers, and I have tried to synthesis but the yield is low. I used iron powder ...
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0answers
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Why is F a bad leaving group? [closed]

Why is F a bad leaving group? I thought that a good leaving group is one that tends to leave easily (=strong acid or weak base) and is stable (ergo a weak base or a strong acid). So wouldn't F be a ...
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0answers
14 views

Mechanistic detail for Dehydration of benzaldoxime with acetic anhydride reaction [closed]

Please draw out and explain the mechanism for Dehydration of benzaldoxime with acetic anhydride rection. I'm struggling to find anything about it. Thank youuu :)
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0answers
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Comparing rate of dehydration [closed]

First I made the products and tautomerised them As the conditions for dehydration are not mentioned so I assumed acidic conditions. This means that all the compounds would follow $E^1$ mechanism. This ...
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1answer
375 views

(E)-2-bromo-1,4-difluoro-3-iodobut-2-ene or (E)-3-bromo-1,4-difluoro-2-iodobut-2-ene

I am struggling with naming this structure either (E)-2-bromo-1,4-difluoro-3-iodobut-2-ene or (E)-3-bromo-1,4-difluoro-2-iodobut-2-ene. I am aiming at the question whether there is also a ...
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0answers
46 views

How can I weigh the compound that melts at room temperature?

I am conducting an organic synthesis experiment involving 2,3,5-tribromothiophene. The melting point of 2,3,5-tribromothiophene is about 25-28 ℃, so it melts easily during weighing. Whenever I weigh ...
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0answers
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Why (abundance of M+1)/(abundance of M)=(number of carbon atoms)*(1.1/100)?. Why simple unitary method and arithmetic doesnt work? derive the formula [closed]

what is the proof of the formula and how the formula works? why combinatorics and distributions have been involved in the calculation? why cannot we find the number of carbon atoms just by using ...
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1answer
59 views

Is bromo(iodo)fluoro(chloro)methane possible?

So this compound is supposed to have all of the stable halogens a part of this molecule ,fluorine,chlorine ,bromine and iodine. Is it really possible? Link :http://wiki/...
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1answer
41 views

Stability of hydroxy aldehydes [closed]

I cannot understand if carbonyl adjacent to alkene stabilises or destabilises it. Generally, we say that more substituted alkene is stable. In those cases attached groups increase electron density of ...
3
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2answers
79 views

Mechanisms for Reimer-Tiemann and Kolbe-Schmidt reaction on deuterium labelled phenol

I was solving a bunch of reactions when I encountered the following: So for the first question: This is a Reimer-Tiemann reaction. I felt that the tautomerism would result in the deuterium getting ...
1
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1answer
54 views

Determining the most stable enolic form of 1-phenylbutan-1,3-dione?

Question Which form of 1-phenylbutan-1,3-dione is more stable? Answer 3-Hydroxy-1-phenylbut-2-enone My question I've been told that between the above two, 3-hydroxy-1-phenylbut-2-enone is more ...
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1answer
52 views

Carbocation stability + determining position of attack on a carbocation in SN1 reaction

It's implied that the right structure is the more stable carbocation because it undergoes the second half of an SN1 reaction, but I'm not entirely sure why: I'm also not sure why the $\ce{MeOH}$ ...
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1answer
27 views

How does the concentration of a liquid increase? [closed]

Here the answer is A, I thought that both solids and liquids had constant concentrations and only aqueous solutions and gasses have changes in concentration. how does adding extra ester increase the ...
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0answers
50 views

Comparing the degree of dehydration

I am confused regarding the following problem which asks to arrange the given compounds in decreasing order of their degree of dehydration My attempt at the solution: I tried to find out the ...
4
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1answer
163 views

Assigning E–Z configuration for alkenes with cyclic substituent groups [duplicate]

I was taught that according to CIP rules, we must check the priority order for the substituents. But how can we do the same for molecules with cyclic groups as substituents? How do we compare the ...
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0answers
14 views

Identification of functional group [closed]

my own solution A R + NH3 + → NH4NO3 R = HNO3 HNO3 = liquid NH4NO3 = solid Accelerates the burning of combustible material. Produces toxic oxides of nitrogen ...
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4answers
269 views

What is an example of chemical reaction that can be assisted by both an inorganic catalyst and an enzyme?

I have been researching chemical reactions of inorganic catalysts and enzymes and cannot find a chemical process where an inorganic compound can be replaced by an enzyme (or vice versa) and have the ...
2
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1answer
165 views

How can a compound having a plane of symmetry be Chiral?

The compound( Given in the image below) is treated with $\ce{excess H2 in Pt}$. Here, (a) - The given compound. (b) - What the answer should be according to me. (c) - What the actual answer is: Q1 - ...
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0answers
27 views

Stability of organic carbocations. Aliphatic vs aromatic hydrocarbons [closed]

What is relatively more favourable, the formation of carbocations in aliphatic hydrocarbons or in aromatic ones? How aromaticity dictates (if it does) the answer to the above question?
2
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1answer
54 views

Why is Maleic Acid more soluble in water than its trans isomer Fumaric Acid?

My teacher taught me that compounds having intramolecular H-Bonding are relatively less soluble in water as they will not involve in H-Bonding with water appreciably while those able to do ...
2
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0answers
81 views
+50

How stable is Remdesivir when vial vacuum is broken and/or it is reconstituted with sterile water?

I was recently looking at how long can Remdesivir be stored in its different forms. I came up across several articles provided by the FDA and Gilead Sciences and others. What caught my eye was the ...
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2answers
22 views

Determination of the molarity of the diluted vinegar [closed]

Procedure of determination of acetic acid in vinegar 10 ml of vinegar is diluted with distilled water to the mark in a 100 ml of volumetric flask. Then, 20 ml of this diluted vinegar is pipetted into ...
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2answers
43 views

Intramolecular Cannizzaro reaction product

I came across the following question : My reasoning was as follows : It can't be option (c) because there is no chance of losing a carbon during Cannizzaro's reaction It can't be option (b) because ...
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0answers
26 views

Alcohols are a homologous series. However, you can get aromatic, aliphatic and alicyclic alcohols. Are there separate homologous series for each type? [closed]

In my textbook, it says that alcohols are one homologous series with the hydroxyl (-OH) functional group. However, there are aromatic, aliphatic and alicyclic alcohols. In one homologous series, can ...
2
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0answers
43 views

Can't aluminium chloride do electrophilic substitution as an electrophile?

In halogenation reaction of benzene, $\ce{AlCl3}$ is used as a catalyst in order to form electrophile $\ce{E^+}$. So I was wondering that $\ce{AlCl3}$ is a Lewis acid (that fact being also used in ...
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0answers
46 views

Chlorination of (1S)-1-phenylethan-1-ol to (1S)-2-chloro-1-phenylethan-1-ol

I am wondering if it is possible to chlorinate/brominate (1S)-1-phenylethan-1-ol on the second carbon of the ethanol. Though unconventional given that it is usually made by the enantioselective ...
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2answers
149 views

NMR spectrum chemical shift confusion

Recently started on NMR spectrum, and I'm slightly confused about chemical shifts and their connection to the resonance frequency and magnetic field. From what I know, the "new" way of doing ...
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1answer
45 views

Phase of reaction between glucose and potassium cyanide to form amygdalin

I'm trying to write a detective-fiction novel, and I was wondering if potassium cyanide reacts with sugar only if the glucose for the amygdalin to form is dissolved in liquid or does it react even if ...
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0answers
23 views

Confusion regarding reaction pathway followed in reaction with lucas reagent

Recently I came across a problem involving Lucas reagent. It asks what is the major product when 2-methylbutanol is treated by HCl in presence of anhydrous ZnCl2? The answer says major product is 2-...
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0answers
16 views

How to switch concentration of 30/70 water/ethanol through dialysis? [closed]

I mistakenly dialysed a preparation in ethanol such that it is now 30% water and 70% ethanol. How do i make switch the water/ethanol concentrations (70% water and 30% ethanol) via dialysis again? The ...
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0answers
33 views

Mechanism for removal of trimethylsilyl directly bonded to carbons

I recently came across a scheme for the synthesis of panacene (Sabot et al., 2008OrgLett4629): In this synthesis, the step from 14 to 9 in removes a trimethylsilyl ($\ce{TMS}$) group directly bonded ...
4
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0answers
33 views

Reactivity order of DIBAL-H and diborane with esters and acids

I have been taught in class that DIBAL-H is more reactive towards esters than carboxylic acids while opposite is true for diborane. Also DIBAL-H mentioned is taken under low temperatures (−78 °C). I ...
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0answers
80 views
+50

How does the reaction of Alkyl Halides with sodium nitrite in DMF proceed?

I was aware of the reaction of alkyl halides with Aqueos Sodium Nitrite which results in the formation of an alkyl nitrite but I came across the following reaction and was confused of how that would ...
3
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1answer
31 views

Which has higher priority between unsaturated ring and unsaturated chain in the nomenclature of organic compounds?

According to the IUPAC rules of nomenclature, alkenes have higher priority over rings but what if the ring also contains a double or a triple bond? For eg: Is this compound going to be named as 1-(2-...
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0answers
13 views

About the reaction of Nafamostat [closed]

In this case, doesn't it imine react? I think that only ester part is hydrated though..
1
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1answer
53 views

Properties of stilbene isomers

(E)-stilbene may be separated by crystallization from (Z)-stilbene and the side product of the Wittig reaction, triphenylphospine oxide (TPPO), by using absolute ethanol. My question is why? (E)-...
5
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0answers
145 views

Can cis-trans isomers have same InChI?

From all we know only tautomers should get the same InChI key, or, in case of the second block, if there are lots of stereo centers. However these cases are just collisions, they still have different ...
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1answer
18 views

silyl ketene acetal vs Benzene, which compound has a higher nucleophilicity? [closed]

With the use of Lewis acid Aluminium Trichloride, which one would have a stronger nucleophilicity? Silyl Ketene Acetal (CAS: 31469-15-5) or a phenyl group?
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0answers
25 views

Bond lengths in Fullerenes [duplicate]

I came across this about fullerenes- All carbon atoms are equal and the undergo sp2 hybridisation. Each carbon atom forms three sigma bonds with three other carbon atoms. The remaining electron at ...
0
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1answer
27 views

Positional isomers [closed]

How many positional isomers are possible for the following molecule? (a) 6 (b) 7 (c) 5 (d) 4 To know how many positional isomers for molecule, should I change the position of the functional group ...
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0answers
22 views

Why we mostly consider benzene in terms of aromatic compounds? [closed]

In my elementary school books we always considered benzene as an aromatic compound and performed all reactions through benzene but never any other aromatic compound?
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0answers
22 views

Why does my lab assignment use hexanes (a mixture of isomeric six-carbon alkanes) to isolate limonene from an orange peel?

My lab assignment has us use hexanes (a mixture of isomeric six-carbon alkanes) to extract limonene (a terpene) from the essential oil from an orange peel. I can't find information on whether limonene ...
5
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1answer
99 views

Comparing acidic strengths between benzylammonium ion and phenol

Question Compare the acidic stengths between benzylammonium ion and phenol. I first tried to remove the H+ ion from both of them and tried to compare the relative stabilities of resulting conjugate ...
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0answers
27 views
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0answers
42 views

Why 9BBN's rings don't migrate during hydroboration-oxidation?

My organic chemistry textbook (Clayden, Warren, Greeves) says this: If we use the $\ce{HBR2}$ reagent $\ce{9-BBN}$, then only the non-cyclic substituent formed in the hydroboration reaction will ...
4
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0answers
41 views

What functional group is this in this specific molecule?

I know without the nitrogen this molecule would probably be considered a crown ether. What exactly would the nitrogen/oxygen functional groups be named as in this molecule shown below? Any help would ...
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0answers
27 views

What is the HOMO of a molecule with 8 conjugated electrons? [closed]

I know this is a basic question. Can I just assume that this will work: solve for n in Huckel's Rule (4n+2), so n=1 in a molecule with six pi electrons? And then LUMO is (HOMO + 1)? *Edited to change ...
2
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1answer
35 views

What is the difference between an Aryl Halide and a Vinyl Halide?

Are aryl halides a type of vinyl halide? From my knowledge, when a Halogen atom is directly bonded to a doubly bonded carbon atom it is a Vinyl halide. When we look at halogen atom directly bonded to ...
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0answers
27 views

chemistry 2 final about organic chemistry asap pls [closed]

I need this as soon as possible please. Any help would be appreciated

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