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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.

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Spectroscopy in organic chemistry [duplicate]

I'm sorry if I am posting in the wrong place, I just wanted to ask what are the best textbooks to learn spectroscopy used in organic chemistry ( IR, MS, NMR etc.). Thanks alot in advance!
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0answers
45 views

Reaction of 2-phenylpropanamide with (NaOH/Br2) [on hold]

Please explain why 1-phenylethan-1-amine is produced on reaction with $\ce{NaOH}$/$\ce{Br2}$, but 2-phenylpropanamine is produced due to reaction with $\ce{LiAlH4}$ in ether? I expected that 2-...
9
votes
1answer
211 views

Explanation for bond lengths in trans-hexatriene

Hexatriene is an unsaturated hydrocarbon with six carbon atoms and five carbon-carbon bonds, three of which are double bonds. However, the bond lengths of the $\ce{C=C}$ bonds are not the same. The ...
2
votes
1answer
43 views

Molecular orbital explanation of why the protonation of the oxygen atom makes a carbonyl group more electrophilic

I was working on nucleophilic addition reactions to the carbonyl group (namely, hemiacetal formation) when I came across the following explanation for the use of acid catalyst and how it increases ...
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2answers
87 views

The nomenclature behind “Diacetonamine”

Please explain how the name “Diacetonamine” can be found by looking at the formula: $$\ce{(CH3)2C(NH2)CH2C(O)CH3}$$ Why is it called “Diaceto” if there only one $\ce{-C(O)CH3}$ group?
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0answers
39 views

What is a probable mechanism for acid catalysed decarboxylation of alpha-hydroxy acid?

The following question was on one of the tests we had recently Now i worked out the intermediates and the product as follows: The first step is an intramolecular Cannizzaro reaction in which the ...
3
votes
2answers
65 views

When is donation into an anti-bonding MO stabilising?

This has been puzzling me for quite a while and I'm not sure if it could be a misconception on my part. When is interaction of a filled orbital with a antibonding MO stabilising and when is the ...
2
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0answers
55 views

Where will a H+ attack on 6-hydroxyhexan-2-one? [closed]

Where will a H+ attack on 6-hydroxyhexan-2-one? Protonation can take place either on the ketone or the alcohol. So where will it attack? In short, on which of the two oxygen atoms is electron density ...
2
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0answers
29 views

Is the concept of frontier orbital interactions chiefly a kinetic concept?

Frontier molecular orbital theory has proved to be an immensely useful concept. The concept of HOMO-LUMO interactions are frequently employed in detailing the mechanistic descriptions of reactions in ...
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0answers
15 views

For fluorine as group, effectiveness +M>-I or -I>+M(is F electron donating or withdrawing?)

When fluorine is bonded with carbon of benzene ring, It can act like an +M(electron donating mesomeric) group and -I(inductive) group. +M depends on the successful delocalisation of fluorine's p ...
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1answer
44 views

Friedel–Crafts with unsaturated halides

Which of the following compounds will not undergo Friedel–Crafts reaction with benzene: vinyl chloride or allyl chloride? According to me vinyl chloride will be a better electrophile than allyl ...
0
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0answers
16 views

Which is more acidic 2-Ethylbenzoic acid or 2-Methylbenzoic acid?

Both will undergo Ortho effect But as ethyl group is more bulkier it will show more Ortho effect to -COOH group as compare to methyl Is the above reason is correct?
1
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1answer
41 views

IUPAC nomenclature of aspartame

I'd like some help in constructing the IUPAC name of aspartame: From what I understand there are carboxylic acid, amine, amide, ester, and phenyl groups - but I'm having trouble figuring out the ...
0
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1answer
32 views

Determining the more acidic proton in cyclopenta-1,3-diene

I am in the David Klein textbook in Chapter 3 going over rule 2 of finding the more acidic proton: if the electron pair in the conjugated base is delocalized, then the conjugate base is more stable, ...
1
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0answers
14 views

Effect of solvent polarity on SN1 reactions of different charge types

On the topic of the ionisation mechanism (i.e. $\mathrm{S_N1}$), Carey & Sundberg (2007) discuss the effect of polarity of solvent on the rate of $\mathrm{S_N1}$ reactions of different charge ...
6
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1answer
43 views

Dependence of rates of neighbouring group participation on length of alkyl chain

On the topic on neigbouring group participation, it is mentioned in Carey & Sundberg (2007)[1] that the effectiveness of the participation is dependent on on the ease with which the molecular ...
2
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0answers
53 views

Abnormal reaction of grignard reagent

My book states that: When isopropyl magnesium bromide is added to diisopropyl ketone, the expected tertiary alcohol is not obtained; instead the secondary alcohol; diisopropyl carbinol is obtained ...
0
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1answer
15 views

How would I know that a compound and its isomers are enantiomers? [closed]

How would I know that a compound and its isomers are enantiomers? Considering the chiral carbons Consider the compound is 2-bromo-2-chlorobutanedioic acid.
1
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1answer
40 views

Can't decide between E1 and E2 mechanisms for this reaction

I can see that due to the substrate being bulky, an elimination reaction will take place and not substitution. The reagent is a strong base. E1 reactions are independent of the base chosen, and E2 ...
0
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1answer
37 views

Stability of tertiary carbocation [duplicate]

Our teacher told us that a carbocation connected to 3 cyclopropane rings is among the most stable carbocations. But I am unable to understand how, as resonance (the most important factor governing ...
-2
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0answers
43 views

What is the chirality of 6,6'-dinitro[1,1'-biphenyl]-2,2'-dicarboxylic acid? [duplicate]

I was confused about the chirality of this compound may it has chiral center or not, so please some one should help if it is chiral or achiral.
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1answer
38 views

Is 1-(1-Methyl cyclopropyl) carbocation [1] as stable as Cyclopropyl Methyl Carbocation[2]

Does the extra Methyl group interfere with the exceptional stability of Cyclopropyl Methyl Carbocation?
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0answers
11 views

Lipophilicity computational prediction

Is there a web based (or otherwise) computational chemistry tool which is able to calculate lipophilicity of a given compound?
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0answers
35 views

Organic Chemistry - Reduction

Can anybody help me with the product? Seems like Birch reduction, but Birch reduction is used for conjugated systems and alkynes.
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0answers
30 views

How does the ease of oxidative addition vary with identity of X?

Recently I studied I Heck coupling reaction which starts with oxidative addition, and I've read that the reactivity of halogen in heck coupling is ordered in this way: $$\ce{X = I > Br > OTf &...
1
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0answers
31 views

How is occupation number of lowest unoccupied natural orbital defined?

I have run some calculations to analyse the occupation of natural orbitals. Since it is needed to run in triplet state, I get two orbitals with occupation number 1. Now, which orbital occupation ...
0
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1answer
43 views

Can benzene ring be the part of a acyl group

Can benzene ring attached to c=o i.e carbonyl group be considered as a acyl group?
0
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0answers
40 views

Dehydrogenation/Dehydration of alcohol with Cu

When the vapours of a 1°,2°,3° alcohol are passed over red hot Cu powder at 573K, 1°,2° alcohol undergo dehydrogenation to form an aldehyde or ketone respectively and 3° alcohol undergoes ...
0
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1answer
56 views

What will be the possible conditions to react bromo alkane with diethyl phenylmalonate?

How to react 1-bromopentane with diethyl phenylmalonate? I used NaH (1.5eq) but the yield is less than 30%. I used KOH but yield is low. I used tBuOK and it did not work, I used K2CO3, but not working....
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0answers
18 views

Carrying on a stereospecific 1,4 conjugate addition on a terminal alkyne

I am looking for a way to attack a propiolate ester with a triazole and get the Z isomer of the resulting acrylate selectively. All literature survey can come up with is big nitrogen containing ...
1
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0answers
50 views

What will be the product of the following series of reactions

. The answer given to this question is . This is how I attempted the problem. Considering that my answer and the author's answer is missing only a methyl group, is this a publishing error or am ...
4
votes
2answers
61 views

Regioselectivity in iodolactonisation of γ,δ-unsaturated carboxylic acid

In the last step of the iodolactonisation of 3,3-dimethylpent-4-enoic acid,[1,2] why does the carboxylate attack the iodonium to form a 5-membered ring, when a more stable 6-membered ring is possible? ...
0
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0answers
53 views

Benzene diazonium chloride and ethanol

Benzene diazonium chloride is reduced to benzene by ethanol which itself gets oxidised to ethanal. Most reactions of diazonium salts are due to nucleophilic substitution on the carbon attached to ...
2
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2answers
57 views

How could you accomplish the following transformation in sufficient yield?

I've considered Riley oxidation but the major product would have a hydroxyl group at the benzylic carbon to the left of the double bond instead of the methyl group as shown. Is there a way to make the ...
0
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1answer
34 views

Why does using NaI as a nucleophile and acetone as solvent lead to an SN2 reaction mechanism instead of SN1? Is I- not considered a weak nucleophile?

In a reaction with a secondary leaving group, why does using NaI with acetone as a solvent lead to an SN2 reaction mechanism instead of SN1? I thought that halogens were weak nucleophiles, and only ...
0
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1answer
49 views

Stability of alkene

Sorry for this silly doubt but why is CR2=CH2 alkene more stable than CHR=CHR alkene? Both have same number of alpha hydrogens. I thought that the latter is more stable as in its trans isomer, the R ...
0
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1answer
33 views

What is the use to know that a compound optically active or not? [closed]

What is the use to know that a compound optically active or not? Is it important to know that?
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1answer
22 views

Chain elongation with a substituent

Can this compound exist in a stable form. If so, can it be used to add the chloroethyl group to a carbonyl compound
0
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1answer
59 views

Clarification in the mechanism for Molisch's test for glucose

Wikipedia says Molisch's test is a sensitive chemical test, named after Austrian botanist Hans Molisch, for the presence of carbohydrates, based on the dehydration of the carbohydrate by sulfuric ...
13
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2answers
511 views

Do non-classical carbanions exist?

There are some non-classical carbocations, such as the 2-norbornyl cation, in which the positive charge is heavily delocalised. Have non-classical carbanions also been discovered? I have not seen any ...
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1answer
23 views

How to check leaving group ability of cations?

In the reaction of an ether with a hydrogen halide (HX), the positive hydrogen ion replaces one of the alkyl groups attatched to the oxygen; but why does this happen, isn't the hydrogen ion a better ...
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0answers
29 views

Dehydration of (4-hydroxyphenyl)acetone to phenylacetone possible?

Is a dehydration of (4-hydroxyphenyl)acetone (CAS.770-39-8) to phenylacetone with $\ce{H2SO4}$ possible? Does anybody have some literature on that, cause I searched and didnt find anything.
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0answers
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Are these the intermediate steps for dihydroxylation of an alkene using OsO4?

or perhaps Also, is NaHSO3 required at any point and if so why?
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0answers
6 views

Can iodometry analyse the peroxide radicals of palmitic acid after it has been heated?

I know that oleic acid in palm oil forms hydroxide radicals to form aldehydes in their secondary oxidation. Does a palmitic acid go under a similar process?
4
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1answer
53 views

The carbon-13 NMR for 1,1,1-trichloroethane

I was working the following spectroscopy problem from Clayden 2e that asks us to identify the structure of a compound from information about its carbon-13 NMR peaks. Problem 3.5: The solvent ...
0
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1answer
29 views

Difference in leaving group ability due to variation in nucleophiles

Wikipedia writes: There can still exist contextual differences in leaving group ability in the purest form, that is when the actual group that leaves is not affected by the reaction conditions (by ...
2
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0answers
34 views

What is the origin of chirality in the universe?

I am just curious with the fact that our body is made of so many chiral molecules the DNA that we possess is chiral, the amino acids in our body is chiral and there are many other objects other than ...
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1answer
29 views

From where does nucleophile attack the ketone in a nucleophilic addition reaction ? [closed]

I inserted a picture to help show where my misunderstanding lies. I know that in the nucleophilic addition of ketones and aldehydes , a racemix mixture is produced . And I know that the reason is ...
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0answers
14 views

Reaction between hcfc 141b and isopropyl alcohol [duplicate]

Can 50% 1,1-dichloro-1-fluoroethane react with 50% isopropyl alcohol? Condition: room temperature
2
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1answer
34 views

Acidity comparison between cyclopropene and cyclopropane

There many sources on the internet saying that cyclopropane is more acidic than cyclopropene because the conjugate base in latter would have antiaromaticity which would destabilize it. But in this ...