Draw the reaction mechanism that shows BH3 adding to the alkene. Why do we get the...

Draw the reaction mechanism that shows BH3 adding to the alkene. Why do we get the anti-Markovnikov product?

Solutions

Expert Solution

Why it gives anti-markonikov product

First step is the attack of the alkene on BH₃, which then forms a four membered ring intermediate of partial bonds. It is because of this intermediate that hydroboration forms the anti-Markovnikov product. The boron atom is highly electrophilic because of its empty p orbital (ie. it wants electrons), and forms a slight bonding interaction with the pi bond. Since some electron density from the double bond is going towards bonding with the boron, the carbon opposite the boron is slightly electron deficient, left with a slightly positive charge. Positive charges are best stabilized by more highly substituted carbons, so the carbon opposite the boron tends to be the most highly substituted. Once the transition state breaks down, BH2 is attached to the least substituted carbon.

queen_honey_blossom answered 1 year ago

Next > < Previous

Related Solutions

I. Alkene Properties, Structure, and Reactivity Mechanisms Write a mechanism for the reaction of HX, H3O+,...

I. Alkene Properties, Structure, and Reactivity Mechanisms Write a mechanism for the reaction of HX, H3O+, X2, X2/H2O, with an alkene to produce the corresponding product. Discuss how the Hammond postulate can be used in explaining the basis for the Markovnikov’s rule. Explain the mechanism of catalytic hydrogenation of alkenes using appropriate diagrams and reaction arrows. Explain why the hydroboration-oxidation reaction shows non-MKV regiochemistry Explain why hydrohalogenation and hydration obeys the MKV (Markovnikov) rule. Explain why the alkene halogenation and...

Imine formation with the reaction of aniline with benzaldehyde. Draw mechanism.

How do you draw a reaction profile diagram that shows how the energy of the reactants...

How do you draw a reaction profile diagram that shows how the energy of the reactants progresses into the energy of the products making sure all key points of the diagram can be labeled. For example, what the activation energy and overall reaction energy is. Please provide 3 examples. Then describe how catalysts lower the activation energy of a reaction and how this effects the reaction rate.

Draw the mechanism for the formation of the imine (forward reaction) and the hydrolysis of the imine (reverse reaction.)

1) Draw a mechanism for the reaction of the preparation of dibromosuccinic acid and predict the...

1) Draw a mechanism for the reaction of the preparation of dibromosuccinic acid and predict the stereoisomer formed based on the stereochemistry of the starting material. a) how did you determine experimentally the stereoisomer formed? Explain

Why do you think a third financial statement is important? Do we not get everything we...

Why do you think a third financial statement is important? Do we not get everything we need from the Balance Sheet and Income Statement? What information does the Cash Flow Statement give us that is unique, and why do investors need that information?

A)Draw the mechanism of bromination of cis-2-butene. B)Explain the stepwise mechanism of the reaction between mercury...

A)Draw the mechanism of bromination of cis-2-butene. B)Explain the stepwise mechanism of the reaction between mercury (II) acetate to ethylene C)Explain with suitable examples the concept of E-and Z- alkenes. Is there any difference between Cis/Trans with E/Z ? Justify your answer. D)Cis-2-Butene has a higher boiling point (4 0C) than trans-2-butene (1 0C) — Explain. E)How can you correlate the melting points of oleic acid, linoleic acid and linolenic acids with their double bonds?

Draw in detail the reaction mechanism for the acid (H2SO4)-catalyzed esterification reaction between salicylic acid and...

Draw in detail the reaction mechanism for the acid (H2SO4)-catalyzed esterification reaction between salicylic acid and acetic anhydride to form aspirin. Please include an explanation of the steps of the reaction mechanism.

Why do we need to use a decrement operator to get it to write the numbers...

Why do we need to use a decrement operator to get it to write the numbers in reverse? Write a program that reads a list of integers, and outputs those integers in reverse. The input begins with an integer indicating the number of integers that follow. For coding simplicity, follow each output integer by a space, including the last one. Ex: If the input is: 5 2 4 6 8 10 #include <iostream> #include <vector> // Must include vector library...

Draw the mechanism for the two steps reaction catalyzed by aminoacyl-tRNA synthetases that gives rise to...

Draw the mechanism for the two steps reaction catalyzed by aminoacyl-tRNA synthetases that gives rise to "activated" tRNA

Subjects