Draw a stepwise mechanism for the following reaction. Draw the transition state for each step.

Name: Problem 14, Chapter 10: Organic Chemistry
Uploaded: 2019-06-01T05:46:34-08:00
Duration: 10 min 50 s
Channel: Lashan De Silva
Description: Draw a stepwise mechanism for the following reaction. Draw the transition state for each step.

Draw a stepwise mechanism for the following reaction. Draw...

Key Concepts

Elementary Steps

Elementary steps are the simplest individual reactions that occur within a stepwise mechanism. Each step involves a single event or a fundamental process that cannot be decomposed further. The overall reaction mechanism is the sum of these elementary steps, and their study enables the understanding of kinetic and thermodynamic aspects of the reaction.

Reaction Mechanism

This concept refers to the detailed, step-by-step process by which reactants transform into products. It breaks down the overall transformation into discrete events, or elementary steps, describing the bond-making and bond-breaking processes that occur. Understanding reaction mechanisms is essential for predicting reaction outcomes and solving problems related to kinetics and product distribution.

Stepwise Mechanism

A stepwise mechanism is one in which the overall reaction occurs through a series of individual, sequential steps rather than in a single concerted move. Each step represents an elementary reaction that contributes to the overall transformation. Recognizing a stepwise mechanism helps in identifying intermediates and distinct transition states associated with each stage of the reaction.

Transition State

The transition state is a high-energy, unstable configuration of atoms that represents the point of maximum energy along the reaction coordinate for an elementary step. It is the critical point that must be surpassed for a reaction to proceed from reactants to products. Drawings of transition states help visualize the energy barrier and the rearrangement of bonds occurring during the reaction, offering insights into reaction kinetics and the feasibility of each step.

Transcript

00:13 This problem has to draw a stepwise mechanism for the event reaction before i'd the mechanism let's see what are the reactants so this is the reaction between cyclohexene and hydrogen chloride and it's used the product chloro -cyclo -xyxyxy, so this is alkyene so therefore if you see the product the hydrogen chloride has added to the therefore this is an addition reaction and what is the mechanism of this reaction so it's a electrophilic addition reaction so why alkin has electrophilic addition reactions so you know we can write the alkene molecule in the with the orbitals so the carbon atoms in the double bond is speed to hybridize so you it has three sp2 hybrid orbitals and there's a one unhybridized peabotle so in this double board the one is a sigma bond the other one is a pi bond therefore alkinza electron rich compounds they have high electron density above and below the carbon carbon atom plane therefore any electrifies can attack on this five electrons okay let's see the mechanism of this reaction the first step of the mechanism is the five electrons of the double bond is attack on the hydrogen atom so why it's attack on the hydrogen atom so this hydrogen chloride in this hydrogen chloride chlorine is more electronegative than hydrogen therefore the bond between hydrogen and chlorine has polarized therefore we can write it's delta plus delta minus therefore this five like pi electrons can attack on this positive center and when you write the mechanism make sure you have to draw the valence electrons of atoms the chlorine has six loan pairs so you have to show those loan pairs in the structure okay so there is a two electrons shown that these two carbon atoms two electrons show on this double bone carbon atoms so the one of the carbon atom take the electron from this carbon and it donate to the hydrogen and make a bond therefore in the same time when when the when the when the new bone making between this carbon and hydrogen this bond is heat is more the the bone between hydrogen and chlorine is heat critically dissociate like this so so what is the product it's forming so it's okay so this one gain one hydrogen therefore now this has two hydrogen and and and they are there was hydrogen here so this carbon atom is a one electron therefore it's make a positive here and it's make a carbocator and in the same time it's forming the chloride but make sure you have to show the lone pair electrons of chloride it has a for loan pairs so this is the first step of the mechanism okay now let's the second step so in the second step one of the electron pair of the chlorine is attack on the positive center so we can write this one attack on the positive center and it make a bond with the carbon so what is the product for this is hydrogen hydrogen it has hydrogen it has a hydrogen and new bond with chlorine and make sure so when the one electron is donated to carbon it loses one electron when the chlorine donate one electron to the carbon it lose one electron therefore it's negative charge become neutral and this carbon gain a one electron therefore it's become neutral and chlorine has six three more it has a stream of lone pair electrons so and when you write the mechanism like this always remember you have to draw the arrow from negative to positive look here the negative means the electrons to the positive center you just want dissociated to the glory and here also electrons to the positive okay now let's see what are the transition state of these two steps so let's let's write the transition state of this one it's denote i and this one let's denote double i this transition state let's go the transition state first one now when you when you draw the transition state you have to consider what bonds have what bonds are formed and what bones are broken so if you see the structure here the double bond is broken and there's a new bond form between carbon and hydrogen and hydrogen and chlorine is broken so let's draw the transition state so it has a cyclic cycle and this double bond breaks it means at the beginning there's a double bond here and in the product no double bond therefore we write it in the dotted line and and at the beginning there is no bone between this carbon and hydrogen, but the product has a new bond.

07:56 Therefore, we have to write in the dot as a hydrogen...

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