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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23 views

Why doesn't tetrachloromethane react with aqueous sodium hydroxide under reflux?

$\ce{CCl4}$ does not react with hydroxide nucleophile whereas $\ce{CH3Cl}$ does. I had initially thought that it was due to symmetrical geometry of $\ce{CCl4}$ and so the dipoles cancel out and the ...
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Why do Ferrocene and Nickelocene vary in their properties even though they're similar in structure? [closed]

Got this practice question for my finals but have no clue where to start. Could someone please help answer this? "Ferrocene and Nickelocene are similar in structure but vary in their properties. ...
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Why is Water added when determining peroxide value of oils [closed]

In the process of getting the peroxide values of oils following the standard AOCS method. An amount water is used after adding the KI and then finally followed by titration using sodium thiosulphate . ...
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How do I answer this question? [closed]

A student performs an experiment several times to determine the enthalpy of combustion of naphthalene, an organic compound with the formula C10H8. The student collects the following data: −5182.6kJmol,...
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Why do silyl groups increase the acidity? [duplicate]

I don't understand how a silyl group can increase the CH-acidity. I know that a silicon in beta position stabilizes the carbocation because of hyperconjugation, but how can one explain the ...
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23 views

vitamin D test in mushrooms [closed]

How could I test vitamin D levels in mushrooms? (I am a high school student, our lab is pretty modern, but not as fancy as colleges have). I need it to complete my extended essay experiment
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32 views

How to synthesise 1,3-dioxo-1,3-dihydro-2λ^5-spiro[isoindole-2,1'-piperidin]-2-ylium? Does it even exist?

I saw some quite strange problems on my ochem exam. For instance, there was a question about this cation. I supposed that this is the way of 6-membered ring nucleophilic opening. But searching about ...
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How do you draw the pi MO diagram for the acetate ion CH3COO-

How do you draw the pi MO diagram for the acetate ion CH3COO- ? I get stuck with the number of electrons on the 2p orbital of Oxygen atom. My teacher said 1 oxygen has 1e, the other has 2e. But ...
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0answers
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Does red phosphorus with hydriodic acid reduce all alkyl halides?

$\ce{HI/P}$ is used for reduction of alcohols, aldehydes, ketones and acids to alkanes. As for alkyl halides, I have read that only alkyl iodides are reduced, whereas other alkyl halides do not: $$\ce{...
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1answer
119 views

Complete mechanism of benzotriazole synthesis from o-phenylenediamine

Does my suggested mechanism for benzotriazole synthesis look correct? Are the arrows for the cyclization in the right place? Chemdoodle (which I drew this with) makes the curly arrows look a bit weird....
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how does hyperconjugation changes bond order in alkenes?

I am a high school student and I am little bit confused in hyperconjugation of alkenes, 1)In my textbook its written that bond order of C=C bond changes due to hyperconjugation {sigma-pi resonance) ...
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Preparation of m-nitroaniline from m-dinitrobenzene [duplicate]

Consulting various Organic Chemistry resources, I have found two reactions for the purpose stated in the subject: First reaction: Second reaction: But, I cannot find the reaction mechanism by which ...
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40 views

Why does Fluorine react differently than other halogens during Hydrohalogenation/Halogenation and also substitution with Alkanes?

From what I understand, during halogenation with an alkene or alkyne, diatomic gaseous halogen molecules can effectively 'break' the pi bond to produce a haloalkane/haloalkene. However I discovered ...
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Regarding Baratchotoxin Stability period [closed]

How long the Baratchotoxin tipped darts be stable, like will it have the same toxicity even after 15 years with out being used
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What is the difference between Saytzeff rule and Markovnikov's Rule? [closed]

From what I understand the functional group is placed at the more substituted/hyperconjugated carbon bond/atom. So why different names (Saytzeff/Hoffman Rule and Markovnikov's rule)? What am I missing?...
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Why are the unsaturated fatty acids usually unconjugated?

My textbook gives the structures of the unsaturated fatty acids in food including oleic acid, linoleic acid, linolenic acid and docosatetraenoic acid. I figure that when two or more $\ce{C=C}$ double ...
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What mechanism is this in carbonyl chemistry? [closed]

How can I go from the product on the left to the product on the right, just by having water and acid? I don't see the mechanism involved here.
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1answer
44 views

Organic Brønsted base that is not a Lewis base [closed]

Which non-nucleophilic organic bases get protonated by typical Brønsted acids (like $\ce{HCl}$, $\ce{H2SO4}$) but also don't form Lewis acid–base complexes with typical Lewis acids like $\ce{BCl3}$, $\...
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Confused by Oxygen denoted with superscript "i" [closed]

I have just come across an equation in a textbook in which Oxygen has a superscript "i" notation, the example of the equation given was this. NaO^iPr Does anyone have any idea what this ...
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2answers
66 views

When doing free radical substitution, is the free radical a catalyst?

Consider a simple free radical substitution's propagation step for $\ce{CH4}$ to $\ce{CH3Cl}$: $$ \begin{align} \ce{CH4 + Cl^. &-> CH3^. + HCl}\tag{R1}\\ \ce{CH3^. + Cl2 &-> CH3Cl + Cl^.}...
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23 views

Nitrocellulose using Sodium Bisulfate instead of Sulfuric Acid

Recently, I came across this question with regards to making nitrocellulose using only nitric acid and not sulfuric acid: Nitrocellulose (flash paper) synthesis without Sulfuric Acid? One of the ...
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0answers
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% of ionization [closed]

Estimate the % of ionized form present at pH 7.4 for: -aspartic acid with a pKa of the side chain= 3.9 -lysine with a pKa of the side chain= 10.5 -histidine with a pKa of the side chain= 6 -tyrosine ...
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1answer
53 views

Is Na/H2 a reducing agent? [closed]

This is a question from my today's test.I have a doubt why Na/H2 wont be a reducing agent as it should form metal hydrides.
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1answer
128 views

Can the environment of a molecule affect its HOMO LUMO gap?

For example, if a particular molecule is inside a particular protein, can its absorption maxima change with respect to the isolated molecule? Also, within the same protein, can the molecule's HOMO-...
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2answers
58 views

What is the rate law of a reaction: 2A + 3B → products?

Update: I found out that the coefficients of the chemical reaction are not the exponents in the rate law. It is actually the order of the species during the reaction. It is known that in the reaction, ...
3
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1answer
75 views

Why is selenophene aromatic?

According to Wikipedia, The selenophene molecule is flat and aromatic. Being aromatic, it undergoes electrophilic substitution reactions at the 2- or 2,5-positions. These reactions are slower than ...
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Methyl or phenyl carbocation is more stable [closed]

Is methyl carbocation or phenyl carbocation is more stable?
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1answer
70 views

Forming conjugate acid of borate anion via protonation

I am a biologist so please forgive me as I likely won't be as rigorous as a professional chemist. I am using the RDKit package to extract organic molecules from salts, where one ion is organic and the ...
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0answers
42 views

How to identify chiral carbon in rings [closed]

Chiral carbons are tetravalent and are bonded to 4 different groups, easy to see when we are dealing with carbons in a chain however, this is difficult when dealing with a ring. Consider the following ...
3
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1answer
54 views

Naming of an organic compound containing nitrogen and fluoride

I'm don't have a background in chemistry but I've been doing a project on computer aided molecular design and one of the resulting molecules was: I'm having trouble naming this molecule let alone ...
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0answers
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Why isn't phosphoric acid catalyzed synthesis of alcohol from alkene widely used?

Almost everything I can find on this reaction uses dilute sulfuric acid, and mentions that phosphoric acid can also be used. But many sources say the opposite, that phosphoric acid is used to ...
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0answers
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What is the difference between Cholestanol 5alpha and 5beta?

What is the isomeric relation between 5Alpha Cholestanol and 5Beta Cholestanol. I know that those forms appear after Hydrogenation of Cholesterol but unfortunately I cannot find any article or ...
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1answer
119 views

Are there any organic compounds with three or more oxygen atoms bonded together in a straight chain?

Recently, there was a question which enquired about some oxygen rich compounds that burn themselves completely and thus not requiring any external atmospheric oxygen. The author came up with the ...
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3answers
148 views

Do molecules containing enough oxygen to burn themselves exist?

Is there a molecule with enough oxygen in it (for example, something like $\ce{HCOOOH}$) such that it can undergo complete combustion without requiring any additional oxygen? For example the above ...
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0answers
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Electrophilic substitution on disubstituted benzene, when deactivating groups are at para

As far as I have been able to understand this, the sites of electrophilic substitution are majorly decided on basis of the fact that "Where the electron density is more, electrophilic ...
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1answer
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what's the importance of "s" character in hybrid orbitals?

I am a high school student and I am learning about hybridization, my teacher told me that it is due to the "s" character in the hybrid orbital that they can arrange themselves so that the ...
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2answers
272 views

Identification of endo and exo products in this Diels-Alder reaction

This synthesis example is shown in the book Cycloaddition Reactions in Organic Synthesis by S. Kobayashi and K. A. Jorgensen (link), on p. 15: 8 is a chiral catalyst, which can be ignored, in the ...
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0answers
35 views

Is there a way, formula, to calculate the possible amount of enantiomers and diastereomers in molecule?

So I have to calculate the max. possible number of enantiomers and diastereomers from a molecule(in my case beta-D-glucopyranose). I know that the stereoisomers are calculated using 2^n, where n is ...
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0answers
13 views

chromatographic interactions with methanol, acidic or basic?

How can I describe the interaction between methanol and thiophene in a chromatographic separation in an acid media? I'm confused with the different concepts: Methanol present a hydrogen acceptor ...
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1answer
42 views

Burning vegetable oil as fuel [closed]

I heard just recently that vegetable oil (i.e palm oil) does burn. I am also aware that burning used motor/engine oil, does emit hazardous gases such as nitro or sulfur oxide, hence prohibited by ...
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2answers
63 views

Why is the major product of an elimination reaction an alkyne and not the diene?

1,2-Dibromopropane and KOH react together to form propyne. But I wondered if 1,2-propadiene was also being produced since the there is also a proton on the $\ce{CH3}$ group to be used in the ...
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0answers
40 views

Why is a branched alkane more stable than the straight-chain isomer?

My text book says that branched alkanes are more stable than their straight-chain isomers, but does not give any explanation. Is this merely a fact, or something that can be logically rationalized ? A ...
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0answers
25 views

Mechanism of this addition-elimination process

In Part 1 of the synthesis of Maoecrystal V (found on synarchive), the last step subjects a $\ce {\alpha, \beta}$-unsaturated ketone to $\ce {I2}$ and pyridine, as shown below: I am wondering what is ...
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0answers
38 views

Bond frequency vs Bond Strength in Kinetic Isotope Effect

I am confused by the following: in Ansyln's Modern Physical Organic Chemistry, a higher vibrational frequency defines a stronger bond due to the deeper/sharper potential well (page 76). However, the ...
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2answers
89 views

When does an aromatic ether break its bonds?

I was reading some reactions of ethers and I came across Zeisel determination. Later that day, I was asked to determine the products of the reaction : And I made the product: This reaction is ...
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1answer
80 views

Number of chiral centers in Proline

I think it's two, but I am not able to access/find any information on the net that supports my claim or justifies why it's wrong. One chiral center is the obvious carbon attached to $\text{-(COOH)}$ ...
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1answer
83 views

IUPAC name of benzoyl chloride

I came up with two possible names: benzoyl chloride and benzene carbonyl chloride. I believe both names are correct. Wikipedia says that the preferred IUPAC name is benzoyl chloride: Can someone ...
3
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2answers
96 views

2-Pyridone tautomer ratio

The following excerpts from different textbooks about keto–enol tautomerism in pyridones seem to be contradictory. Could someone explain which one is right? MARCH’S ADVANCED ORGANIC CHEMISTRY pg-103 ...
2
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1answer
59 views

Conversion of cyclohepta-1,3-diene to cyclohepta-1,3,5-triene

In the landmark synthesis of tropinone by Willstatter in 1901, an interesting step involves the use of $\ce {Br_2}$, quinoline to convert cyclohexa-1,3-diene to cyclohexa-1,3,5-triene. In the scheme ...
2
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4answers
92 views

Hydride shift or Methyl shift

For the carbocation (A) given in the reaction, first we can rearrange it by ring expansion (4 to 5) then we have two choices either H-shift or methyl-shift. My teacher told me that Hydrogen is the ...

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