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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307 views

What are the states of HX when reacting with alcohol and alkenes respectively, and Br2 when reacting with benzene?

I couldn't find this in any textbooks, so I guess I will ask this here. What is the physical state of $\ce{HX}$ when reacting with alcohol (nucleophilic substitution) and alkenes (electrophilic ...
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1answer
158 views

Can freezing break up sugar polymers?

I recently freezed a huge bunch of apple slices, and thawed them again a few days later. After thawing, I noticed a few things compared to a batch that I had put in the fridge (no freezing) The ...
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4answers
10k views

Why don't alcohols undergo nucleophilic substitution with ammonia?

Alcohols can undergo nucleophilic substitution with $\ce{PCl5, POCl3, HCl}$. Halogenoalkanes can undergo nucleophilic substitution with $\ce{NH3}$. The $\ce{C-O}$ (in alcohol) and $\ce{C-Cl}$ (in ...
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169 views

How to change CO₂ to a less polluting gas?

I want to change $\ce{CO2}$ coming out of the tailpipe of a car to some other compound that is considerably less harmful to the environment with a filter of some sort. What are some ways that this is ...
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2answers
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Which among phenol and 1,2-dihydroxybenzene has the higher boiling point?

My attempt Based on symmetry: I think that looking for symmetry phenol has a higher boiling point than 1,2-dihydroxybenzene because the two -OH groups projecting out from the benzene ring of 1,2-...
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3answers
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Why are allenes chiral?

How is 1-bromo-3-chloropropa-1,2-diene ($\ce{BrHC=C=CHCl}$) chiral? It doesn't have any carbon that is connected to four different groups.
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747 views

Phenyl vs methyl cis/trans stability

Compound I is obviously the Z isomer. I thought it was obviously the less stable one too, given that there's a phenyl and t-butyl on the same side. The answer says that since the phenyl is planar, it ...
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1answer
3k views

How can I determine the boiling point of a compound using simple distillation?

I've graphed a distillation curve (temperature against volume of distillate) from the data obtained from a simple distillation experiment. The substance can be any of methanol, ethanol, 1-propanol or ...
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1answer
233 views

Balancing chemical systems - searching and sorting preliminary information

I was hoping I could get help finding ways to sort information in the problem. What kind of information does "the conversion of toluene to benzene..." give us that is relevant towards solving the ...
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1answer
8k views

How to calculate mole ratio of two volatile compounds in distillation?

I have two volatile compounds (such as ethyl acetate and ethyl propionate). I am going to separate these compounds by simple and fractional distillation. How do I calculate mole ratios of the two ...
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6answers
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Will bridged compounds the undergo SN1 reaction?

$\mathrm{S}_{\mathrm{N}}1$ reaction involves only one molecule in the rate determining step. So, the molecule which undergoes $\mathrm{S}_{\mathrm{N}}1$ reaction should be stable when it forms a ...
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1answer
3k views

Best reagent for reducing a ketone in the presence of an alkene

The following reduction is best accomplished with: (a) Zn/Hg, conc. HCl (b) N2H4, C2H5ONa (c) H2, Pd (d) All of the above My thoughts: By looking at the question it is evident that ...
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1answer
166 views

Temperature & time necessary to carbonize all organics

Suppose that I have a cast-iron pot which my awful roommate has vigorously scrubbed with soap and left to soak in soapy water over the weekend. The seasoning has been destroyed and replaced with awful-...
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1answer
10k views

What are identical molecules?

I don't know what identical molecules are but these are by thoughts. Since from the word identical the molecules should have the same number and kind of atoms attached in the same way. Since in ...
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1answer
17k views

How to check for geometrical isomerism in cyclic compounds?

I have no problem with identifying whether a given molecule has geometrical isomerism if it's not cyclic. But cyclic compounds are confusing for me. For eg: How to check whether the following molecule ...
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1answer
1k views

Do lone pairs contribute towards the pi electron count of heterocycles?

I'm not able to understand how the following compounds are aromatic. When should the lone pairs on heteroatoms be taken into consideration when counting the number of π electrons?
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2answers
1k views

Why do pharmaceutical drugs have a expiration date?

Every now and then you reach into the bathroom cabinet to find that some pill or ointment you where planning to use has gone past its expiration date. I am interested whether this expiration date has ...
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1answer
141 views

Naming of a molecule [closed]

$\ce{H2C=C=O}$ what is the group of the molecule? How to characterize it and how is this dissimilar to ketone? If we add $\ce{O2}$ with it then will we get $\ce{CO2}$?
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Is the nomenclature “primary”, “secondary”, “tertiary”, and “quaternary” carbon atoms limited to sp3 carbon atoms?

In organic chemistry we can classify carbon atoms as primary, secondary, tertiary, or quaternary based on the number of additional carbon atoms bonded to the carbon atom of interest. The definitions ...
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2answers
3k views

How will citric acid be deprotonated by pyridine?

Why do we deprotonate that specific hydrogen as opposed to any other one? What information does the table on the right give us? It seems unrelated to citric acid - where does the fluorine come from?
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2answers
4k views

Predicting electronic geometry, observable geometry, and hybridization for any atom in a molecule

Can someone please explain the intuition around the answers to this problem: I'm finding it very confusing because it seems like you have to nitpick between two resonance structures to get the ...
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1answer
756 views

How to properly work with potassium HMDS

What is the proper procedure for working with KHMDS? I would like to use it to deprotonate a compound and have a bottle of KHMDS in toluene. Does it need to be handled under inert atmosphere? And ...
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1answer
86 views

On nomenclature of certain compounds

I have some questions on the nomenclature- (1) In $H_2O$ we have $H$ written first and $O$ is second but when it comes to Hydroxyl group $OH$ the $O$ comes first, Why? (2)Why is Propanal called ...
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1answer
556 views

References for learning about acid and bases in organic chemistry

I was wondering if someone could help me find references available that will help me solve the following problems. These are not homework problems, but are suggested problems that were given to me by ...
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1answer
880 views

References to draw 3D molecules with directionality of non-bonding electron pairs and p-orbitals

My instructor has been drawing 3D molecules that show the directionality of non-bonding electron pairs and p-orbitals. I've been trying to find references online that show this process, but I'm having ...
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2answers
945 views

Lone pair electrons on secondary carbon vs primary carbon

I know that a molecule is more stable when a free radical is on a secondary carbon over a primary carbon, but how about when there is a lone pair of elections that can be placed on a secondary or ...
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2answers
15k views

Hybridisation of the negatively charged carbon atom in a carbanion

Given the carbanion, $\ce{R3C-}$, the carbon is $\mathrm{sp^3}$ hybridized, unless it is participating in resonance. This is clear from its steric number. However, I am having trouble in drawing its ...
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1answer
828 views

Would Chlorine or Chloramine gas show up on a VOC test?

Would Chlorine or Chloramine gas show up on a VOC test? My apartment was cleaned using chlorox and lysol, and there has been a smell that's been lingering for about 10 days. The air was tested with ...
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3answers
7k views

What causes the smell in rotten meat-grease and how can I get rid of it thoroughly?

We've just spilled the can of used meat-grease we collect so that it doesn't go down the drain and it turns out it was rotten. Now the granite counter-top and the wood-laminate floor of the kitchen ...
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1answer
4k views

Molecular chirality and optical rotation

Why does having molecular chirality result in optical rotation? The dissymetry or chirality of molecules translates to the rotation of plane polarized light, the magnitude and direction depending on ...
18
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1answer
13k views

Migratory aptitude in Baeyer-Villiger reaction

In short, I do not understand how or why the migratory aptitude is as listed in every textbook I've read. Firstly, they talk about a positive charge being built up that is stabilised by the movement ...
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1answer
542 views

How did the first amino acids appear on Earth?

Is there proof or a theory that shows that the first amino acid syntheses on Earth were influenced by a change in heat, gravity, radiation, or something similar?
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1answer
383 views

What is the reaction mechanism for the hydrolysis of Amifostine?

I have to do research on a drug called Amifostine: 2-(3-aminopropylamino)ethylsulfanyl phosphonic acid. I'm supposed to say how the organic reaction works inside the body. I understand that it ...
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1answer
635 views

Organic compounds that react with carbonate ions

I want to remove carbonate ions from dissolved potassium carbonate (potash) by letting an organic compound react with the carbonate ions. I don't have a very good knowledge of organic chemistry, but ...
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1answer
269 views

What happens in the attempted diazotisation of 1,2-diaminobenzene?

Usually, $\ce{NaNO2}$ and $\ce{HCl}$ are the reagents used to generate an aryldiazonium chloride from an aniline. However, in this compound there are two amine groups adjacent to each other, so it ...
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1answer
172 views

Transesterification of propylene carbonate and methanol

I'm going to try out the transesterification of propylene carbonate and methanol. I know that the mechanism is as follows : -What are the products yielded after the reaction? -And which catalyst ...
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4answers
24k views

Why is acetic acid more acidic than phenol?

Acetic acid (ethanoic acid, $\mathrm pK_\mathrm a \approx 5$) is more acidic than phenol ($\mathrm pK_\mathrm a \approx 10$), which is reflected in their reactivity with a weak base such as sodium ...
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3answers
122 views

Are sulfonyl-carboxylates stable in water?

This time I am interested in a specific type of acid anhydride, sulfonyl-carboxylates, i.e. compounds with the following molecular structure: where $\ce{R2}$ can be an organic substituents or ...
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2answers
1k views

Are aromatic amines or amides less basic?

When the lone pair of an amino group $\ce{R-NH2}$ is involved in resonance, its basicity decreases. But, between conjugation with carbonyl group $\ce{R}=\ce{R'CO}$ or resonance with benzene $\ce{R} = \...
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1answer
140 views

Is the current situation possible for recreaction in a lab?

I want to convert cellulose to another form (crystalline => amorphous). Cellulose requires a temperature of 320 °C and pressure of 25 MPa to become amorphous in water.(Is the pressure achievable in ...
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2answers
4k views

Does the hydrolysis speed increase when more H+ ions are in the solution?

In hydrolysis of polysaccharides, does the hydrolysis speed increase when more $\ce{H+}$ ions are present in the solution? So if I were to use $\ce{H2SO4}$ instead of $\ce{HCl}$ (same volumes) then $\...
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1answer
19k views

NaHCO₃ + HNO₃ → NaNO₃ + H₂O + CO₂ … but something weird happens to me in practice

I put 98% white fuming nitric acid and then I pour some sodium bicarbonate expecting $\ce{NaNO3}$ being formed, I'm not really using much water because it will make evaporation takes ages, even so $\...
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3answers
5k views

Is there any special rules for checking the aromaticity of polycyclic compounds?

This question arose in my mind because it's given in a book that pyrene is aromatic. How can it be with 16 π electrons? So, it should be actually anti-aromatic or is there any special rule for these ...
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1answer
4k views

Can we predict Dextrorotatory and levorotatory character of an organic molecule?

Can we predict in which direction a given molecule will bend plane polarized light? If I have a molecule with R form in R-S nomenclature does it mean that the molecule will be dextrorotatory or is ...
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1answer
7k views

Figuring out formula of a hydrocarbon from amount of products obtained and reactants used

One mole of a hydrocarbon is combusted. The products obtained are cooled down to STP and occupy a volume of $89.6\:\ell$. Oxygen required for conbustion was $145.6\:\ell$ at STP. Find the molecular ...
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1answer
2k views

index of hydrogen deficiency

I don't really get the concept of index of hydrogen deficiency (IHD). Can someone please use an example to explain what $\mathrm{H_{reference}}$ and $\mathrm{H_{molecule}}$ are? I know the formula: $$...
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1answer
167 views

preparation methods of nicotinoyl glycine

How can we prepare nicotinoyl glycine from nicotinic acid ?Is that possible by reaction between nicotinic acid and glycine?
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1answer
942 views

Is it possible to create an acid anhydride that's stable in water and if so what conditions must its structure satisfy?

I ask this question because if acid anhydrides are always unstable in water then my interest, as a student of pharmacology, would be greatly diminished. Acid anhydrides are, in my books, at least, the ...
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1answer
8k views

Finding chiral carbons in aromatic or cyclic compounds

I know that for a carbon to be chiral four different groups should be attached to that particular carbon. But, what about in the case of cyclic compounds? What's the method to check chirality if the ...
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1answer
526 views

Is there a difference between imidazolidinone and imidazolidone?

I've had my nose in the early literature on GFP (Green Fluorescent Protein), which contains a 4-(p-hydroxybenzylidene)imidazolidin-5-one fluorophore, and in one paper the author refers to the "...