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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.

7
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0answers
41 views

Exceptionally weak basicity of pyridine [duplicate]

It is often explained that the relatively lower basicity of pyridine, relative to most amines, is due to the fact that the $\ce {N}$ lone pair resides in an $\ce {sp^2}$ hybridised orbital, instead of ...
2
votes
0answers
86 views

Why might the yield of my synthesis of triphenylmethanol be so poor?

I performed the classic Grignard reagent formation leading into the preparation and purification of triphenylmethanol using phenylmagnesium bromide as my Grignard, and benzophenone as the reagent for ...
2
votes
3answers
95 views

How does hyperconjugation lead to stability?

I know that hyperconjugation leads to delocalization of electrons between filled and unfilled orbitals and thus greater stability (that's what most textbooks said). However, I think that it reduces ...
0
votes
1answer
72 views

Aromaticity fails?

Why is cyclopentadiene ($\mathrm{p}K_\mathrm{a} = 16$) less acidic than A) 2,4-pentanedione ($\mathrm{p}K_\mathrm{a} = 9$); B) phenol ($\mathrm{p}K_\mathrm{a} = 10$)? C) Even H20 (pka = 15.7) ...
4
votes
1answer
68 views

Why does the proton NMR of ferrocenecarboxaldehyde appear to be four singlets?

One singlet stems from the aldehyde H, and another from the Cp ring with 5 hydrogens attached. However, the ring with the aldehyde group attached has hydrogens in two chemical environments which are ...
1
vote
1answer
43 views

Nomenclature of carbohydrates

In the chapter on Biomolecules in my book, the following points are given regarding carbohydrates. Numbering the C-chain with consecutive rank The C-atom present in the aldehyde group of ...
0
votes
1answer
57 views

Amount of enantiomers

I got a question about this molecule, and I'm not sure how to answer it. I know that this one has 4 chiral C-atoms, but I can't seem to get the number of enantiomers right. I know that the formula for ...
3
votes
1answer
84 views

Why are pi antibonding orbitals lower in energy than sigma antibonding orbitals?

I know when a carbonyl group is attacked by a nucleophile, the electrons of the nucleophile enter the antibonding π orbital of the $\ce{C=O}$ bond, which breaks the π bond. My textbook says that ...
-2
votes
1answer
34 views

Will fruits and vegetables be more oxidized if blended at high speed for a long time or at less rpm for a short period of time? [closed]

Will fruits and vegetables be less oxidized if blended at higher speeds for shorter periods of time, or at lower speeds for longer periods of time? Do the oxidized molecules in vegetable juice ...
0
votes
1answer
44 views

Where can I find reliable data for melting points of organic compounds?

I'm interested in the melting/freezing points of organic compounds, but the online literature has data that's all over the map. I can understand that especially for isomers of alkanes, pure samples ...
0
votes
2answers
38 views

What are methods of identifying which amino acids are in a sample of protein? [closed]

Are there any methods out there to identify which amino acids are in a sample of protein? Perhaps using NMR?
0
votes
1answer
18 views

How would you go about adding a Cl group para to a brominated cinnamic acid? [closed]

We recently synthesized brominated cinnamic acid in lab, and now our goal is to add a Cl para to the R group attached to the benzene ring.
0
votes
0answers
51 views

On what factors do melting and boiling points depend upon?

In my book there is a separate discussion given for trends in melting and boiling points in each chapter in inorganic chemistry (the chapters on the various groups like group 15, group 16, etc.) and ...
1
vote
2answers
145 views

Why total heat of hydrogenation of 1,3-cyclohexadiene is more than that of benzene?

I'm told that heat of hydrogenation (HOH) is directly proportional to number of π bonds and inversely proportional to stability. So, is the aromaticity responsible for this? Also, what is the general ...
-1
votes
1answer
40 views

Organic Nomenclature [closed]

10.2 It has to add 4-propyl is that correct? And 10.3 why do we choose the position 1,5 instead of 2,3?
1
vote
1answer
47 views

Fragmentation involving formation of enamine

I have a problem on fragmentation which requires mechanisms involving formation of an enamine from a cyclic ketone and cyclic secondary amine. This then reacts with a cyclic aldehyde via conjugate ...
0
votes
1answer
81 views

Which organic compound's NMR and IR are these? Can't find out. (Data available: Melting Point ~ 116 °C)

Which organic compound's NMR and IR are these? I have figured out that the compound is a 1,4 substituted benzene. And the substituents are probably not -COOH and -OH from the spectroscopy. Kindly help ...
1
vote
1answer
49 views

How to write correct NMR integrals in a formula?

for my masterthesis I want to include the Equation how I calculate my conversion in a polymer reaction. It is pretty easy, but I still want to write it down. Basicly the equation is: (Integral A ...
1
vote
1answer
31 views

When a bond is formed between an electophile and a nucleophile, they both lose energy and become more stable right?

This is a section from clayden's organic chemistry textbook. I do not understand why it says energy gain and not energy loss
0
votes
1answer
40 views

Aminoethyl or ethylamine?

I was trying to name the above compound which happens to be 3-(2-aminoethyl)-2-methylcyclohexan-1-ol. On my first attempt, I had named it 3-(ethyl-2-amine)-2-methylcyclohexan-1-ol. Which one is ...
3
votes
1answer
78 views

Ability to produce hydrogen gas on reaction with Na/K

Out of a given set of compounds, I was asked to identify which would produce hydrogen gas on reaction with Na/K. One of the given compounds was: I could not detect any acidic hydrogen in it, so ...
2
votes
1answer
48 views

What is the name of this organic compound?

The organic compound in question is shown above. This is how I tried to name it: Start from the left hanging $\ce{H_3C}$. $\ce{OH}$ gets the number 2 and $\ce{NH_2}$ gets 6. The lowest numbers ...
1
vote
1answer
123 views

Which will be the major monochlorination product? [closed]

Which of these compounds represents the major monochlorination isomer formed in the following reaction? According to selectivity theory, the answer should be (c). However, the given answer is (...
-1
votes
1answer
62 views

Why is a carbon to iodine pi-bond less stable than a carbon to fluorine pi-bond?

This question comes from a second semester undergraduate organic chemistry course. Please refer to the image below with regard to the question. My understanding of the trend in section 4a is that "...
0
votes
1answer
48 views

Why doesn't self condensation occur in acetoacetic ester synthesis

So, I came across a quite versatile method to synthesize aldehydes and ketones, its called the Acetoacetic ester synthesis. Suppose I need some 2-pentanone. So to synthesize it via this method I can ...
-1
votes
1answer
23 views

Separation of sugar and fat in a column chromatography [closed]

I am chemist at organic and bioorganic chemistry,I want to know if we are separating sugar and fat in a column chromatography who will be down first ? and why ? Thank you.
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votes
1answer
26 views

How can I use a solvent gradient in column chromatography? [closed]

I am working to use the column, there are a lot of videos which explain it, but I don't understand this statement in the procedure. The residue was finally purified by column chromatography using ...
0
votes
1answer
92 views

Carbanion Stability [closed]

I was wondering that wether a Cross-Conjugated or a Extended-Conjugated carbanion is stable I have sort of memerise that a Cross-Conjugated one is more stable For example, Which of the Carbanion is ...
0
votes
1answer
52 views

Confusion regarding the Shape of XeF4 [closed]

I found on internet that the shape of $\ce{XeF4}$ is square planar but what if one place $2$ of $\ce{F}$ on the equitorial position and rest two on axial position and the two lone pair on the leftout ...
0
votes
0answers
39 views

How to Remove Sugar from Lime Juice to Make it Less Sticky?

I am thinking of making a citrus air freshener with natural ingredients, but I do not want a sticky juice going on the fabric that are in my house. What are some ways (from easy household methods to ...
-3
votes
1answer
57 views

Bond-line structure of 2-methyl-3-phenyl-1-butanol

According to me the structure of 2-methyl-3-phenyl-1-butanol is the above one. Is my answer correct?
-1
votes
1answer
59 views

Predict stereochemistry of product [closed]

When 3-methyl(1,1-2H2)pent-1-ene reacts with HCl, why do we obtain a racemic mixture? The given reactant is optically pure.
2
votes
1answer
217 views

Grignard Reagent in THF vs in Diethyl ether

While learning about the Grignard reagent I was taught this by my teacher, but I couldn’t justify why it was so.. I cannot see how Grignard reagent would react differently in basically an ethereal ...
-1
votes
2answers
29 views

Methanol vs water. Acidic strength [duplicate]

Why $CH_3OH$ is more acidic than $H_2O$ while the same is opposite for other alcohols?
-1
votes
2answers
50 views

How is 2-hydroxy-ethoxy named?

2-hydroxy-ethoxy is $\ce{HO-CH2-CH2-O}$. I have a couple of confusions regarding this substituent. Ethoxy is $\ce{-HO-CH2CH2}$ or $\ce{-OC2H5}$. So the $\ce{HO}$ in the above formula probably ...
0
votes
2answers
49 views

Percent hydrogen and carbon [closed]

A 1 g sample of an organic compound was burned in a combustion analyzer and yielded 1.42 g carbon dioxide and 0.872 g of water. Calculate the percent carbon and hydrogen in the sample. From the ...
0
votes
0answers
46 views

Will ether group undergo cleavage in this molecule?

So, I've got to tell what will be the product after treating with dilute acid. I'm sure that oxygen next to carbon 7 will get protonated resulting in carbon oxygen bond cleavage to generate a stable ...
-1
votes
1answer
29 views

which one is the correct statement of “Law of definite proportion”? [closed]

according to my genius Teacher ' this law state that "the composition of a compound in terms of atoms (Not Mass) remains constant". His Proof: H2O and D2O are similar compounds (because H and D have ...
0
votes
0answers
52 views

Steric Factors on reaction with grignard reagent

I was asked to find the products X and Y. For the product X,Here the grignard reagent and even the carbonyl substrate was too sterically hindered to approach the carbonyl center so no reaction would ...
-1
votes
1answer
66 views

Simple soda–lime decarboxylation

This is my homework question I tried it hard the question is as follow: I attempted it as follow: According to my understanding as acid base reaction are fastest the carbanion will gain a $\ce{H+}$. ...
8
votes
1answer
144 views

Ring contraction when cyclohexene oxide is treated with methyl Grignard

My book writes that: Recall that epoxides rearrange with Lewis acids in a pinacol-like fashion, and that Grignard reagents in THF exist in the following equilibrium: I approached this ...
0
votes
2answers
88 views

How do dibromopyrazolones undergo base-promoted decomposition?

I was not sure but seeing the base as NaOH I used the fact that it will take most acidic hydrogen that is N-H and electron pair will come over it and it will resonate from two sides. I could make upto ...
1
vote
0answers
78 views

Kolbe's electrolysis of acetylenedicarboxylic acid

I have been wondering what this reaction would lead to? The ethyne diradical can't dimerize because triple bonded cyclic structures don't form until 8 carbons. And even if it polymerizes I find no way ...
5
votes
1answer
83 views

Conformer generation for radicals

Is there an automatic way to generate conformers for radical like systems (spin multiplicity is doublet)? My system for the study is a substituted fullerene with a missing H atom from the functional ...
0
votes
1answer
46 views

Compare stability of the given carbocation

Give the order of stability of the given carbocations. Usually stability is determined by studying effects taking place in the carbocation. All are resonating and there is no diff in inductive effect....
0
votes
0answers
36 views

Should I use MCPBA here?

I came across a question that asked for a method to convert propene to glycerol. I used the method in the pic, but I'm worried about two steps- Step-2, This reaction is just made up by myself! I'm ...
0
votes
0answers
24 views

Aliphatic resin (wood glue) and Kerosene

Is it safe to combine wood glue and kerosene? Will the polymer chain length be destroyed? The thought is that i could stabilize wood slabs by driving the wood glue polymers into the wood by ...
-1
votes
1answer
42 views

Opening the imidazoline ring in tolazoline

Hello. I was studying about the alkaline ring opening or purines. While doing research, i came across this compound. This got me thinking if we can use the same procedure to open the imidazoline ring ...
0
votes
0answers
29 views

Regarding Clemensen Reduction of the following compound [duplicate]

While I was doing problems on reduction of aldehydes and ketones, I encountered this particular question Here, I know that Clemensen reduction reduces the ketone group to $-CH_2-$ group. But, the ...
1
vote
1answer
61 views

Why does Oxygen act as Nucleophile over here?

We were taught in class that when a carbon atom and an oxygen atom both have a negative charge in a resonating structure, then carbon atom attacks the nucleophile rather than oxygen atom because it ...