**Diels-Alder Lab** 1) **Lecture on the Topic** 2) **Diels-Alder Lab** - [Watch the video](https://www.youtube.com/watch?v=W4mGgnu4bAM) 3) **For Post Lab, Answer the Following Questions:** a) **Provide the structure of the major organic product in the following reaction.** - Reaction: A cyclic diene with two chlorine atoms reacts to form a cyclohexene derivative with two chlorine atoms attached on adjacent carbon atoms. b) **Provide the organic product of the following reaction.** - Reaction: A diene with two methoxy groups reacts with a dienophile containing an ester group to form a cyclohexene derivative with methoxy and ester groups attached. c) **Provide the organic product of the following reaction.** - Reaction: A methoxy-substituted diene reacts with a nitrile-substituted dienophile to form a cyclohexene derivative with methoxy and nitrile groups. d) **What diene and dienophile would react to give the product below?** - Product: A cyclohexene derivative with a formyl group. - Reactants: A diene with a formyl group and a methyl-substituted dienophile. e) **What diene and dienophile are used in the Diels-Alder route to the compound shown?** - Product: A bicyclic compound with nitrile groups. - Reactants: A cyclopentadiene and a nitrile-substituted dienophile. **Explanation of Diagrams:** - Each reaction diagram shows a curved arrow indicating electron movement from the diene to the dienophile, resulting in the formation of a cyclohexene derivative. - Arrows above or below the reaction indicate heating (Δ), which is often required for Diels-Alder reactions. - The structures include specific functional groups such as chlorine atoms, methoxy groups (H₃CO), ester groups (CO₂CH₃), nitrile groups (CN), and formyl groups (CHO), denoted at appropriate positions on the rings.
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.
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3) **For Post Lab, Answer the Following Questions:**
a) **Provide the structure of the major organic product in the following reaction.**
- Reaction: A cyclic diene with two chlorine atoms reacts to form a cyclohexene derivative with two chlorine atoms attached on adjacent carbon atoms.
b) **Provide the organic product of the following reaction.**
- Reaction: A diene with two methoxy groups reacts with a dienophile containing an ester group to form a cyclohexene derivative with methoxy and ester groups attached.
c) **Provide the organic product of the following reaction.**
- Reaction: A methoxy-substituted diene reacts with a nitrile-substituted dienophile to form a cyclohexene derivative with methoxy and nitrile groups.
d) **What diene and dienophile would react to give the product below?**
- Product: A cyclohexene derivative with a formyl group.
- Reactants: A diene with a formyl group and a methyl-substituted dienophile.
e) **What diene and dienophile are used in the Diels-Alder route to the compound shown?**
- Product: A bicyclic compound with nitrile groups.
- Reactants: A cyclopentadiene and a nitrile-substituted dienophile.
**Explanation of Diagrams:**
- Each reaction diagram shows a curved arrow indicating electron movement from the diene to the dienophile, resulting in the formation of a cyclohexene derivative.
- Arrows above or below the reaction indicate heating (Δ), which is often required for Diels-Alder reactions.
- The structures include specific functional groups such as chlorine atoms, methoxy groups (H₃CO), ester groups (CO₂CH₃), nitrile groups (CN), and formyl groups (CHO), denoted at appropriate positions on the rings.](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2F63e2e494-b56f-474b-94e6-a1b0d865891f%2Feb46e9b6-0e47-48ec-9e61-1d3b3418df48%2Fsqluid_processed.png&w=3840&q=75)
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