2,220 Answered Questions for the topic organic chemistry

Organic Chemistry Resonance Ph Reaction Mechanism

07/09/19

Why does depurination happen at a higher pH (or under less harsh conditions) than depyrimidation?
I've always wondered why the N-glycosidic bond, which connects the adenine or guanine purine bases to their sugars, was the easiest to cleave via acid hydrolysis, or why purines have the lowest... more
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Organic Chemistry Polarity

07/09/19

Difference of dipole moments of dichloromethane and trichloromethane?
Why is the dipole moment of $\\ce{CH2Cl2}$ ($1.60 ~\\mathrm{D}$) greater than that of $\\ce{CHCl3}$ ($1.08~\\mathrm{D}$)? Based on my knowledge of vectors, I feel it should be the other way around.
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Organic Chemistry Redox

07/09/19

How many hydride ions are available in NaBH4?
Different sources have different answers. In the reduction of an aldehyde or ketone to an alcohol by Sodium Borohydride, how many moles of aldehyde are reduced by one mole of Sodium... more
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Organic Chemistry

07/08/19

What is Catenation and Tetravalency?
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Organic Chemistry Acid Base Reaction Mechanism

07/07/19

Why concentrated sulfuric acid for dehydration and dilute for hydration?
To dehydrate ethanol one uses concentrated sulfuric acid: $$\\ce{C2H5OH ->[\ ext{conc.} H2SO4] C2H4 + H2O}$$ but to go in the reverse direction, dilute sulfuric acid is used: $$\\ce{C2H4 +... more
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Organic Chemistry Isomers

07/07/19

How to determine number of structural isomers?
I have come through many questions in which they ask to give number of possible structural isomers. For example number [structural isomers of... more
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Organic Chemistry Molecular Structure Vsepr Theory

07/06/19

Why are the two CH2 groups in allene perpendicular to each other?
Allene, $\\ce{H2C=C=CH2}$, has two $\\ce{=CH2}$ groups perpendicular to each other. This is the same as hydrogen peroxide's $\\ce{H}$ atoms. Is there any reason why they adopt the perpendicular... more
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Organic Chemistry Nomenclature Stereochemistry

07/05/19

Can you have a meta stereocenter?
Imagine a compound such as 1,3-dibromo-1,2,3-trichloropropane. Since the first and third carbons are attached to four different groups, they are both chiral centers. Assuming that both of these... more
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Organic Chemistry Physical Chemistry

07/05/19

Why do branched chain compounds have lower boiling points than the corresponding straight chain isomers?
> The branched chain compounds have lower boiling points than the corresponding straight chain isomers. For example, > >- $\\ce{CH_3CH_2CH_2CH_2CH_3}$ - No branching-Pentane (n-pentane)... more
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07/05/19

Why do BH3 and NaBH4 have different selectivities?
I've always known borane ($\\ce{BH3}$), as a reagent for alkene hydroboration. Recently in class we talked about its use in the reduction of carboxylic acids to alcohols as well. Now obviously... more
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07/05/19

Does unsubstituted benzoic acid not show resonance due to steric effects?
My book says that benzoic acid does not show resonance as the carboxylate anion and the benzene ring are not in the same plane due to steric effects. But there aren't any large groups in the... more
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07/03/19

What is a non-classical carbocation?
- What is a non-classical carbocation? - How is it different from a classical carbocation? I am confused as I have come across this term many times on Chem.SE but there seems to be nothing for... more
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Organic Chemistry Quantum Chemistry

07/02/19

What is occuring on the quantum level when a molecule rotates plane polarized light?
What is occuring on the quantum level when a molecule rotates plane polarized light? Also, why do enantiomers then rotate light in opposite directions? I would think that the electromagnetic waves... more
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Organic Chemistry Reactivity Carbonyl Compounds

07/02/19

Why is a ketone more nucleophilic than an ester?
I guess the ester is a weaker nucleophile because it does have an additional oxygen atom, unlike the ketone, that is pulling electrons from the C-O double bond towards the carbon atom (this happens... more
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Organic Chemistry Stability Carbocation

07/02/19

What exactly is "B-strain"?
On factors that influence the stability of carbocations, I came across this peculiar one: > Bulky groups attached to the positively charged $C$-atom (of the carbocation), stabilize it by... more
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Organic Chemistry Molecular Structure

07/01/19

Why isn't cyclobutane planar?
In short, cyclobutane adopts a certain, non-planar, configuration in order to reduce ring strain caused by the fact that carbons are $\\mathrm{sp^3}$ hybridised. That much is understandable. In an... more
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Organic Chemistry

07/01/19

What is the chemical bonding of hydrocarbon and halogenated aromatic hydrocarbon?
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Organic Chemistry

07/01/19

what is the possible chemical bonding of aromatic hydrocarbon?
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06/27/19

Why do thiols have such a propensity for bonding with mercury?
Historically, thiols $\\ce{-SH}$ were known as "mercapto-" due to their strong propensity to bond with mercury. Certain drugs still carry this designation, though... more
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Organic Chemistry Notation Nomenclature Bond

06/27/19

Correctness of writing H3C as opposed to CH3 in a carbon chain?
I have been studying alkanes, alkenes & alkynes for a while, and I see in the examples that all the basic structural formulas start with $\\ce{CH3}$, then $\\ce{CH2}$, and the last carbon atom... more
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06/27/19

Does (2-fluoroethyl)benzene undergo elimination via E1cb or E2?
I have seen in two different sources claiming that $\\ce{PhCH2CH2F}$ gives styrene $\\ce{PhCH=CH2}$ when treated with alcoholic $\\ce{KOH}$, but one source suggests an E1cb mechanism, while the... more
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Organic Chemistry Solubility Alcohols Solvents

06/27/19

How do I predict the solubility of a compound in a mixture of water and an organic co-solvent?
I'm trying to predict the solubility of long alcohols (e.g. 1-octanol, 1-decanol or 1-dodecanol) in a mixture of water and an organic co-solvent such as DMSO, acetonitrile or ethyl acetate. For... more
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Organic Chemistry Halides Stereoselectivity

06/27/19

Why don't alkynes undergo preferential anti bromination to the degree that alkenes do?
Alkenes, for the most part (unless there is a phenyl group or highly ionising solvent) undergo almost exclusively anti addition of bromine. However, under similar conditions alkynes, although... more
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06/26/19

Why is a hydroxyl group more activating than a methoxy group in electrophilic aromatic substitution?
Why is phenol more reactive towards electrophilic substitution than methoxybenzene? Isn't the lone pair on the methoxy group oxygen more available for participating in resonance into the ring than... more
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06/26/19

Is it possible, chemically, to change a dextrorotatory compound to its levorotatory counterpart?
Is it possible, chemically, to change a dextrorotatory compound to its levorotatory counterpart? E.g., is it possible to change dextrodopa to levodopa?
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