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14 Answered Questions for the topic reaction mechanism

Reaction Mechanism Organic Chemistry

07/17/19

What is the role of sulfuric acid and mercury(II) sulfate in the oxymercuration of alkynes?

I have a homework problem where I'm given a terminal alkyne. The goal of the problem is to choose the reagent that will result in a particular ketone. Here's a really general view of the reaction... more
Reaction Mechanism Organic Chemistry Resonance

07/17/19

Which compound reacts faster in the Cannizzaro Reaction?

> Which reacts faster in the Cannizzaro Reaction? >a) $\\ce{OHC-C6H4-NO2}$ b) $\\ce{OHC-C6H4-OCH3}$ Obviously, a better hydride releasing group will react faster. Therefore my answer was... more
Reaction Mechanism Organic Chemistry Resonance

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
Reaction Mechanism Organic Chemistry Acid Base

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
Reaction Mechanism Organic Chemistry Redox

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
Reaction Mechanism Organic Chemistry Elimination

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
Reaction Mechanism Organic Chemistry Synthesis

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?
Reaction Mechanism Organic Chemistry Regioselectivity

06/26/19

Why do SN2 reactions of alkyl halides proceed differently with KCN and AgCN?

Alkyl halides react with $\\ce{KCN}$ to form alkyl cyanides as the main product, whereas the use of $\\ce{AgCN}$ leads to isocyanides as the chief product. Why does this happen?

04/22/19

Stability of cyclobutyl methyl carbocation?

I know that cyclopropyl methyl carbocation is exceptionally stable compared to say, benzyl carbocation. But I want to know how stable is cyclobutyl methyl carbocation compared to say,... more
Reaction Mechanism Organic Chemistry Wittig Reactions

04/08/19

Wittig versus Corey–Chaykovsky reaction?

The Wittig and Corey–Chaykovsky reaction both involve an ylid, phosphonium ylid in the former versus a sulfonium ylid in the latter, attacking a carbonyl compound. I am looking for an answer that... more
Reaction Mechanism Organic Chemistry Carbohydrates

04/08/19

How exactly do sulfites prevent oxidation of wine?

I know that sulfites are used in wines to prevent oxidation, but how exactly does this happen, which reactions take place and where do the products go?
Reaction Mechanism Organic Chemistry Carbocation

04/07/19

Saturated vs unsaturated fats - Structure in relation to room temperature state?

I'm sure most of us have heard that saturated fats are solid at room temperature, and unsaturated fats are liquid at room temperature. I'm wondering how this relates to their chemical structure --... more
Reaction Mechanism Organic Chemistry Halides

03/15/19

In the Favorskii rearrangement, why doesn't the base grab the alpha hydrogen of the carbon bearing the halogen?

In the Favorskii rearrangement, the base (like hydroxide) always abstracts the alpha hydrogen of the carbon not bearing the halogen. But to me the hydrogens on the carbon directly connected to the... more
Reaction Mechanism Organic Chemistry Carbocation

03/13/19

Why is acetone so cold?

I have a summer job as a custodian and one cleaner I use is called Goof Off, which is pretty much just acetone. Another is a disinfectant which is mostly water. How come whenever I put the acetone... more

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