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Answer by Chakravarthy Kalyan for Why does the tautomerism of purine favor...
The given purine has two structures as shown below.In $\ce{9H–Purine}$ (figure 2), lone pairs are far apart from each other (3 and 7). Comparatively in $\ce{7H–Purine}$ (figure 1) lone pairs are very...
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Answer by Chakravarthy Kalyan for Resonance and mesomeric effect
The relevant resonance structures of the given molecule are as follows.Structure A is shown below. NItrogen with 2 sigma bonds is linear as shown below. However , nitrogen in the ring is strained with...
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Answer by Chakravarthy Kalyan for Number of sterioisomers of...
The given compound 2,3,5,6-tetrachloroheptane has 10 isomers. These have been shown below.The compound 2,3,5,6-tetrachlorooctane in the link does not have a meso compound. The terminal groups, methyl...
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Answer by Chakravarthy Kalyan for Acidic cleavage of ether with a 2° alkyl group
what happens if a ether with a 2° alkyl group and a 1° alkyl group is cleaved with a halogen acid?To this question I have drawn a scheme below. The given ether is $\ce{2^0}$ group to the left and...
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Answer by Chakravarthy Kalyan for Which has the highest enol content?
The extent of enol content can be explained on the basis of acidic hydrogen, intramolecular hydrogen bonding.The stability of the carbanion formed is dependent on its stability after it is formed. In...
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Answer by Chakravarthy Kalyan for Are all lone pairs considered as π-electrons?
I am quoting from http://www.hutters-online.de/publikationen/dmchdo.html.One requirement that is basic to this concept and is agreed upon by most authors is that there have to be two double bonds that...
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What is proximity effect?
From Klein's Organic chemistry [1, p. 780]:The 1,2-adduct is believed to form more rapidly as a result of a proximity effect. Specifically, the carbocation and the bromide ion are initially very close...
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Will phosphorous Ylide participate in carbene generation and insertion?
The following question was sent to me . The answer for this question was given to me as option bI attempted it as following , recognizing the first step as a ylide reaction with a carbonyl compound.In...
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Answer by Chakravarthy Kalyan for Odd looking carbocation stability order
If hetro atom with lone pair is neighboring to carbocation, then that lone pair can be donated to empty orbital on carbocation (see figure below). These orbitals are said to be in conjugation....
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Answer by Chakravarthy Kalyan for SN2 reactions and inversion of...
Here I have a compound with 2 chiral centers. There is only inversion at Carbon with iodine undergoing $\mathrm{S_N2}$ reaction. The second carbon does not undergo $\mathrm{S_N}$ reaction. There is no...
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Which is the correct mechanism for the ozonolysis of an alkyne?
According to Organic Chemistry by Jonathan Clayden, Nick Greeves and Stuart Warren (2nd edition), the mechanism for alkene ozonolysis is given asIn Advanced Organic Chemistry, Part B: Reactions and...
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Answer by Chakravarthy Kalyan for Reaction mechanism of rearrangement
The first step is nucleophilic substitution.It is possible for nucleophile to attack directly at the allylic position, displacing the leaving group in a single step, in a process referred to as...
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Answer by Chakravarthy Kalyan for Which is the most acidic hydrogen in vitamin C
Compare the $\ce{OH}$ bonds in Vitamin C (ascorbic acid) and decide which one is the most acidic. The most acidic proton in ascorbic acid is the one whose conjugate base is most resonance...
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Which functional group gets reduced first?
The following is a reduction reaction. In the reduction of 2 to 3, keto group undergoes reduction by nucleophillic addition.Ester could undergo nucleophillic acyl substitution to give an aldo group,...
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Which of the canonical structures contributes more to resonance hybrid?
I am quoting a rule on resonance from Organic Chemistry by T.W. Graham Solomons, Craig B. Fryhle, 12th edition, page 25.Structures in which all the atoms have a complete valence shell of electrons...
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Answer by Chakravarthy Kalyan for What Are Examples of Reducing Sugar in...
Quoting from medium.comIf it wasn’t for Maillard, we would not have juicy seared steak, deep fried chicken wings, nor grilled sausages. All these browning, aromas and flavor bursts are a result of...
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Answer by Chakravarthy Kalyan for What atom would be protonated first in a...
In the given moleculeD's lone pair on oxygen is in conjugation with C=O group. Consequently it acquires a positive charge, its Kb is less for protonation to take place (as shown in scheme 1, as pointed...
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Will ferrocene undergo electrophilic aromatic substitution?
Ferrocene has two structures (1 and 2). It is bonded to the aromatic cyclopentadienyl anion. Aromatic species such as benzene, cyclopentadienyl anion undergo electrophilic aromatic substitutions.Then,...
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Answer by Chakravarthy Kalyan for Nucleophilicity in polar aprotic solvent...
let me start with nucleophilicity of halides. In protic polar solvent, $\ce{F^-}$ is more solvated (hydrogen bonding) than $\ce{I^-}$ and hence less reactive.In polar aprotic solvent$\ce{F^-}$...
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Why is porphyrin aromatic?
I was asked which of the following were aromatic:My understanding of aromatic nature is, that the molecule must be cyclic, planar, every atom in the ring must be $sp^2$-hybridized and the molecule must...
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