2. Our knowledge of chair conformations allows us to use them to determine a great deal about a reaction's mechanism. In particular, using a t-butyl group to 'fix' a cyclohexane in a single conformation can help us learn about the spatial requirements and energetics of a reaction. Consider the following two reaction products: 1) NaCN CN 2) H* OH 1) NaBH4 2) H3O+ OH Group -H -CN -OH A Value (kcal/mol) Defined as 0 0.2 kcal/mol 1.0 kcal/mol a. Draw the most stable chair conformation for each of the two products. b. Based on the A values in the table above, do the two products have the most stable conformation at the new stereocenter?
Reactive Intermediates
In chemistry, reactive intermediates are termed as short-lived, highly reactive atoms with high energy. They rapidly transform into stable particles during a chemical reaction. In specific cases, by means of matrix isolation and at low-temperature reactive intermediates can be isolated.
Hydride Shift
A hydride shift is a rearrangement of a hydrogen atom in a carbocation that occurs to make the molecule more stable. In organic chemistry, rearrangement of the carbocation is very easily seen. This rearrangement can be because of the movement of a carbocation to attain stability in the compound. Such structural reorganization movement is called a shift within molecules. After the shifting of carbocation over the different carbon then they form structural isomers of the previous existing molecule.
Vinylic Carbocation
A carbocation where the positive charge is on the alkene carbon is known as the vinyl carbocation or vinyl cation. The empirical formula for vinyl cation is C2H3+. In the vinyl carbocation, the positive charge is on the carbon atom with the double bond therefore it is sp hybridized. It is known to be a part of various reactions, for example, electrophilic addition of alkynes and solvolysis as well. It plays the role of a reactive intermediate in these reactions.
Cycloheptatrienyl Cation
It is an aromatic carbocation having a general formula, [C7 H7]+. It is also known as the aromatic tropylium ion. Its name is derived from the molecule tropine, which is a seven membered carbon atom ring. Cycloheptatriene or tropylidene was first synthesized from tropine.
Stability of Vinyl Carbocation
Carbocations are positively charged carbon atoms. It is also known as a carbonium ion.
![2. Our knowledge of chair conformations allows us to use them to determine a great deal about
a reaction's mechanism. In particular, using a t-butyl group to 'fix' a cyclohexane in a single
conformation can help us learn about the spatial requirements and energetics of a reaction.
Consider the following two reaction products:
a.
NO NID
ALOH
1) NaCN
2) H+
1) NaBH4
2) H3O+
OH
Group
-H
-CN
-OH
A Value (kcal/mol)
Defined as 0
0.2 kcal/mol
1.0 kcal/mol
Draw the most stable chair conformation for each of the two products.
b. Based on the A values in the table above, do the two products have the most stable
conformation at the new stereocenter?](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2Fef179162-973e-41f0-bb3a-1bfb38a065ce%2Fcae7fbfc-3c57-435d-b68d-fa42f5cf85eb%2Fc4txxxf_processed.png&w=3840&q=75)
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