3. Stereochemistry. Give the structure of the major product formed for each of the following reactions. Provide an explanation for your choice of stereochemistry. OTMS a. 1. BnO дома 160 °C (sealed tube) b. Me -Me 2. HF, CH3CN, rt 3. PDC, 4 Å mol. sieves, CH2Cl2 180 °C B toluene (sealed tube) 70% a. LIN(TMS)2, TMSCI LOSEM THF,-100 °C b. warm to rt C c. 5% aq HCI workup 71% Et SEM CH2CH2SiMe3 A 97%
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.
![Stereochemistry. Give the structure of the major product formed for each of the following reactions. Provide an explanation for your choice of
160 C(sealedtube)
2.HF,CH3CN.n
stereochemistry. a.
->
A 97% HF, CH, CN, rt PDC, 4A mol. sieves, CH2Cl2 A97% ic. a. LiN(TMS), TMSCI THF
, -100°C b. warm to rt c. 5% aq HCl workup C 71%
3. Stereochemistry. Give the structure of the major product formed for each of the
following reactions. Provide an explanation for your choice of stereochemistry.
a.
1.
OTMS
BnO
CO₂Me
160 °C (sealed tube)
Me
b.
-Me
2. HF, CH3CN, rt
3. PDC, 4 Å mol. sieves, CH2Cl2
180 °C
B
toluene
(sealed tube)
70%
C.
a. LiN(TMS)2, TMSCI
LOSEM
THF,-100 °C
b. warm to rt
с
c. 5% aq HCI workup
71%
Et
SEM CH2CH2SiMe3
A
97%](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2F62f5c8a1-ec74-458c-ab2c-94b9dc30ef88%2F23dd7992-4b16-416a-b0fe-5d1b498324d0%2Fhqt948q_processed.jpeg&w=3840&q=75)
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