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.

Filter by
Sorted by
Tagged with
1
vote
0answers
43 views

Glyoxylic acid synthesis

In my quest for a non-electrochemical glyoxylic acid synthesis, I've found a few that seem simple and pretty OTC. The first is the reduction of oxalic acid with magnesium metal, which if I'm not ...
7
votes
0answers
59 views

Identifying Structure based off 1H-NMR & Mass Spectroscopy Data [closed]

I have almost the whole night trying to identify this structure with no avail as there is always one part that does not fit. The determined formula for this structure was $\ce{C13H17BrO}$ from the $m/...
1
vote
1answer
25 views

Combustion and pyrolysis of sulfides and organosulfurs

Last week there was a huge fire in french chemical factory Lubrizol, we now know the main products that burnt, to simplify the discussion I extracted a few compounds: isobutyl and isobutene ...
2
votes
1answer
104 views

Selection of parent chain (IUPAC nomenclature)

In the given compound, there are (apparently) two possibilities of choosing the parent (main) chain for its nomenclature in accordance with IUPAC rules: (A) being the one containing 4 carbon atoms ...
1
vote
0answers
25 views

Diastereoselectivity in the zinc-mediated Barbier allylation

Penumati & Kommu (2014) report the stereoselective synthesis of (+)-$\alpha$-conhydrine from R-(+)-glyceraldehyde. In their synthesis, the imine 6 underwent a zinc-mediated Barbier allylation to ...
5
votes
1answer
394 views

Chain with double bond or triple bond

In this hydrocarbon there can be two main chains: one with two double bonds and one with a double and a triple bond Both main chains contain seven carbon atoms. Which will be considered correct and ...
1
vote
0answers
32 views

Radical addition and radical cleavage of cyclohexene and cyclohexane

Using reaction mechanism, why radical bromination of cyclohexene is faster than cyclohexane? Draw the stereochemistry of most stable product(s) of both cyclohexene and cyclohexane. Here are what I ...
7
votes
1answer
393 views

Reduction of carbamate with LAH

The products of the reduction of esters with $\ce {LiAlH4}$ and the products of the reduction of amides with $\ce {LiAlH4}$ are vastly different. The former reduction cleaves the ester and produces ...
1
vote
1answer
57 views

Why does cyclobutadieneiron tricarbonyl behave aromatically?

It is said that $\ce{(\eta^4-C4H4)Fe(CO)3}$ can undergo electrophilic substitution reactions. Therefore, it displays aromaticity. For the iron atom, it has $8$ electrons in its outer shell initially ...
1
vote
0answers
23 views

Are chlorinated solvents generally avoided in reducing reactions?

Are chlorinated solvents incompatible with reducing reagents? Is reductive dechlorination the reason? There also seems to be exemptions, in J. Org. Chem. 1996, 61, 3849-3862, 1,2-dichloroethane was ...
0
votes
0answers
17 views

butene & ethanol reaction (without an acid catalyzer)

In my organic chemistry class, we were taught that reacting butene and ethanol with an acid catalyzer present would yield acid-catalyzed hydration. However, I was not able to reach a conclusion to ...
2
votes
1answer
33 views

Effect of chloromethyl substituent vs methyl substituent on yields of nitration

The effects of $\ce {-CH3}$ and $\ce {-CCl3}$ substituents on the product distribution of an electrophilic aromatic substitution reaction are unambiguous. The $\ce {-CH3}$ group exhibits a clear ...
1
vote
0answers
53 views

Can anybody help me out with this chain conversion? [closed]

I can understand that grignard reagent will attack the oxygen breaking the double bond of the oxygen forming a diol but that is unstable so it should form a Ketone but after that I can't really ...
8
votes
2answers
2k views

If LPG gas burners can reach temperatures above 1700 °C, then how do HCA and PAH not develop in extreme amounts during cooking?

According to What is the temperature of heat generated from LPG gas?, the temperature of (1) LPG gas is above 1700 degree Celsius. Many of us are familiar with pan-frying meat (steak, pan-frying the ...
1
vote
1answer
229 views

Making aspirin without acetic anhydride

I want to make aspirin. Normal method is to react salicylic acid with acetic anhydride, but it is extremely hard to find acetic anhydride. How may I synthesize aspirin with acetic acid and salicylic ...
0
votes
0answers
35 views

What is the order of stability of the cyclobutyl and cyclopropyl carbocations?

I know about the exceptional stability of Cyclopropylmethyl carbocation. In some books it is given that cyclopropyl and cyclobutyl carbocations are highly unstable due to their high strain. That ...
1
vote
0answers
59 views

Why is t-BuOK necessary for this synthesis?

1-chloro-2-methylpropane --> 2-chloro-2-methylpropane. My understanding is that an E2 reaction produces two types of alkenes, the major product for non-sterically hindered bases is the more ...
0
votes
1answer
42 views

Naming of a dispiroalkane compound

Did I name it right?? Please help me in naming dispiro compounds
6
votes
1answer
136 views

Why does thallium hydroxide increase the yield of product in a Suzuki reaction?

I came across a research paper by Uenishi et al. [1] where relative rates of $\ce{KOH}$ and $\ce{TlOH}$ in Suzuki coupling reactions are compared. Thallium hydroxide increased the yield of products, ...
1
vote
0answers
50 views

If alkyl-substituted alkenes are more stable, how does one explain their increased addition reactivity?

My understanding is that in alkyl-substituted alkenes there is hyperconjugation between $𝜎(\ce{C−X})$ and $𝜋^∗(\ce{C=C})$. I also have read that more alkyl-substituted alkenes are many folds more ...
4
votes
3answers
402 views

Choice of solvent during thin layer chromatography

I understand most of the theory behind TLC and that different volatile solvents have different polarities and cause the 'spotted' substances to move at different rates, but what is the point of ...
2
votes
0answers
79 views

Why do alkyl substituents stabilize alkenes?

My textbook states that because $sp^2-sp^3$ bonds are stronger than $sp^3-sp^3$ bonds, alkenes are more stable than alkanes. The rule given is that bonds with more $s$ character are stronger. However,...
0
votes
0answers
90 views

What is the Criteria for a Compound Being Non-aromatic vs. Anti-aromatic?

Anti-aromatic compounds are formed with a cyclic system of planar, overlapping p orbitals containing a non-Huckel number of electrons (i.e. not 4n+2 electrons -n being a natural number-). Non-aromatic ...
4
votes
0answers
44 views

CuAAC “Click” reaction giving inconsistent results

I apologize in advance for the large amount of text and thank all those who take the time to read it. The "Click" reaction after Fokin and Sharpless is known to achieve high yields without long ...
0
votes
0answers
27 views

Which pathway is better for robinson cycloaddition? 2-phenylacetaldehyde + 3-buten-2-one or 2-phenyl-2-propenal + acetone?

So this was a question on my orgII exam yesterday. The target molecule is 4-phenyl-2-cyclohexenone. By retrosynthetic analysis there is only one possible aldol condensation reaction, but two possible ...
1
vote
2answers
108 views

Can some one please explain alkyl shifts for me

Provide a mechanism for the following reaction. Include all intermediates, resonance structures, charges, and electron pushing arrows to obtain full credit. I’m stuck with this problem. I got ...
0
votes
1answer
67 views

How do I explain the existence of these 2 peaks in this mass spectrometry?

Question about HRMS:Phosphatidylcholines and phosphatidylethanolamines are common types of glycerophospholipids found in biological membranes. Because of the high amount of heteroatom content, ...
4
votes
1answer
66 views

What is the reaction between piperine and concentrated sulfuric acid?

Piperine was chemically characterized by reaction with acids. This was done by dropping concentrated $\ce{HNO3},$ $\ce{HCl},$ and $\ce{H2SO4}$ to a sample of piperine. Both $\ce{HNO3}$ and $\ce{HCl}$ ...
1
vote
1answer
30 views

Basic sites on Indene ion

Answer key says that A is the most basic site but I don’t understand the concept behind that. To assess the basic site, I’d normally look at the molecule as is and assess the current stability of the ...
0
votes
2answers
78 views

Could dimerization account for weak IR signals?

How would you interpret the IR spectrum of your product if it's peaks match the literature spectrum, but the signals are weak? Could the argument that the sample was very dilute and lots of water was ...
1
vote
2answers
116 views

Is there a gauche interaction between C-3 and C-6 in cyclohexane?

To my understanding, a gauche interaction occurs between two R groups when staggered by 60 degrees in a Newman Projection. When looking down the C-1 to C-2 bond of a cyclohexane, the Newman Projection ...
0
votes
0answers
47 views

Can Lugol's iodine differentiate between saturated/unsaturated fats?

We conducted an experiment involving Lugol's iodine where if a substance contained a lipid it would form concentrated areas of color on the sides of the test tube. On many occasions, the test would ...
3
votes
1answer
71 views

Confusion about comparing the charge densities of benzene and fluorobenzene

I understand that the functional group $\ce{-F}$ is an electron-withdrawing group. It is expected that the difficulties of an electrophile to attack the carbon atoms are $$\ce{PhH}<\ce{2,4of PhF}&...
1
vote
0answers
22 views

styrene confusion

I am studying NMR and while looking at styrene, I can't figure out why the two hydrogens on the terminal double bond are not equivalent. Is it because one is closer to the ring in position than the ...
0
votes
1answer
61 views

Is it possible to make micelles to pick up Microplastics from water?

I'd like to know if I could get micelles to pick up microplastics in water. I read that microplastics are sometimes charged, so can we make the lyophobic end to pick up microplastics, so that they can ...
0
votes
0answers
32 views

Hydrogen bonding in o-nitrophenol versus o-nitobenzoic acid

p-nitrophenol is more acidic than o-nitrophenol because of hydrogen bonding in the latter. If I apply the same logic, then o-nitrobenzoic acid should be less acidic than p-nitrobenzoic acid. However, ...
1
vote
1answer
57 views

Using molecular orbital for determining leaving group trend and nucleophilicity

Here is the question. Which one has better leaving group, cyclohexanol or cyclohexane that has $\ce{OH_{2}^{+}}$ substituent? Explain. I know the answer is the latter because if both compounds are ...
1
vote
1answer
46 views

Assigning Cahn-Ingold-Prelog priority numbering rules for 2 groups

I was asked to draw the perspective formula of $$\ce{(3R,4R)CH2=CH-CH(CH3)-CH(CH3)-CH2-CH3}$$ Then I had to assign priority between the two groups: $$\ce{-CH=CH2}$$ and $$\ce{-CH(CH3)-CH2-...
0
votes
1answer
83 views

Which reaction occurs first when 5-hexen-1-ol reacts with sulfuric acid?

I am trying to solve this question: Find the major product of the following reaction: Now we could either do electrophilic addition on the alkene or do dehydration of alcohol. These two ...
1
vote
0answers
35 views

The most acidic hydrogen of 4‐hydroxybutanenitrile

Identify the most acidic hydrogen atom in the compound below: $$\ce{NC-CH2-CH2-CH2-OH}$$ My teacher said that the $\ce{H}$ connected to $\ce{O}$ is the most acidic since $\ce{O}$ is more ...
1
vote
0answers
39 views

Diastereoselectivity of the Pauson Khand Reaction

I hope someone may help me. I don‘t know how to determine the diastereoselectivity of the product of the Pauson Khand reaction in generally. In the following I’ve got 3 practice examples,however in ...
-1
votes
2answers
323 views

Why doesn't ethanol dissolve in sodium bicarbonate?

Today I experimented with different solvents and solutes and was a bit surprised by one result. When I added ethanol to dilute sodium bicarbonate and tapped the test tube against my palm to mix it, I ...
2
votes
0answers
123 views

Why my boiling pot turned black?

Recently I ran out of dish washing detergent, so I decided to pick up one of the recipes online, to make my own "ecological" dish washing detergent alternative. The recipe was: Mix ingredients: ...
0
votes
1answer
69 views

Why does the reaction between 2‐methylbut‐3‐en‐2‐ol and hydrogen bromide show allylic shift?

In the following reaction shouldn't the minor product be the major one as the carbocation formed before attachment of bromine is 3°? Also, can someone tell me why the product includes only ...
2
votes
1answer
488 views

Oxidation of fructose with conc. HNO3

I recently studied carbohydrates. I was taught that fructose on oxidation with strong oxidizing agents like concentrated $\ce{HNO3}$ yields glycolic acid and tartaric acid along with trihydroxy ...
1
vote
0answers
31 views

Volatility comparison for isomers of phthalic acid

All the atoms of these compounds are in a plane. o-phthalic acid can show extensive intra-molecular hydrogen bonding as well as inter-molecular hydrogen bonding. m-phthalic acid can show intra-...
0
votes
0answers
42 views

Does space in between have any significance in IUPAC nomenclature?

The correct IUPAC name of the following compound is: (a) 2,4,6-trimethyl cyclohexanone (b) 1,3,5- trimethyl benzophenone (c) trimethylcyclobutanone (d) 2,4,6-trimethylcyclohexanone I ...
1
vote
0answers
29 views

Dipole moments of dibromoethene isomers

There was an exercise in my textbook asking to compare the dipole moments of 1,1-dibromoethene and 1,2-dibromoethene(Z). The answer in the textbook says that the dipole moment of 1,1-dibromoethene is ...
0
votes
0answers
53 views

How do I name a substituent which is a cycloalkane which is attached by a chain of more than one carbon?

Above is a picture of an alkane. How would I name this using IUPAC rules? I understand how to name other substituents such as (1,1-dimethylethyl) and some other methyl groups, but I don't know how to ...
1
vote
0answers
19 views

Enantiomeric excess catalysed

Enantiomeric excess is defined as $$ee = \frac{[R]-[S]}{[R]+[S]}$$ I found this problem in an IChO paper: "When using the enantiomerically pure (BINOL)Al(OiPr) as a catalyst for reduction of ...