1. A Review of General Chemistry

2. Molecular Representations

3. Acids and Bases

4. Alkanes and Cycloalkanes

5. Chirality

6. Thermodynamics and Kinetics

7. Substitution Reactions

8. Elimination Reactions

9. Alkenes and Alkynes

10. Addition Reactions

11. Radical Reactions

12. Alcohols, Ethers, Epoxides and Thiols

13. Alcohols and Carbonyl Compounds

14. Synthetic Techniques

15. Analytical Techniques:IR, NMR, Mass Spect

16. Conjugated Systems

17. Aromaticity

18. Reactions of Aromatics:EAS and Beyond

19. Aldehydes and Ketones:Nucleophilic Addition

20. Carboxylic Acid Derivatives:NAS

21. Enolate Chemistry:Reactions at the Alpha-Carbon

22. Condensation Chemistry

23. Amines

24. Carbohydrates

25. Phenols

26. Amino Acids, Peptides, and Proteins

27. Transition Metals

[BOOK ORGO] CLUTCH

Diels-Alder Reaction

Predict the products of the following Diels–Alder reactions.

(c) <img src="https://lightcat-files.s3.amazonaws.com/problem_images/f9328ce554cb5071-1670429743799.jpg" alt="" />
(d) <img src="" alt="" /><img class="fr-dib" src="https://lightcat-files.s3.amazonaws.com/problem_images/10e6d0993c571df7-1677635109003.jpg" style="width: 570px;">

How would the following substituents affect the rate of a Diels–Alder reaction?

b. an electron-donating substituent in the dienophile

Careful. The stereochemistry of the dienophile is conserved.

This molecule is not meso. There is no plane of symmetry.

Careful, these are not enantiomers. What happens if you flip one of the molecules like a pancake?


Dienophile stereochemistry:

Because the Diels–Alder reaction is concerted, the relative stereochemistry of the dienophile is conserved. Groups on the same side of the dienophile will be on the same side in the product.


Predict the major, organic product for the following reaction.

<img src="https://media.pearsoncmg.com/ph/esm/ecs_mullins_organic1e/msa/content/practice-test/img/Ch22_Q03_QT.jpg" alt="The figure illustrates a reaction in which the product has to be determined. The reaction contains two reactants. The first reactant has the following structure: A 2-carbon alkane chain is depicted as a line structure using 1 line. C 1 is single bonded to C H 3 on the upper left in the form of a line. C 1 is double bonded to C H 2 on the upper right in the form of two parallel lines. C 2 is single bonded to C H 3 on the lower left in the form of a line. C 2 is double bonded to C H 2 on the lower right in the form of two parallel lines.
The second reactant has the following structure: A 2-carbon alkene chain is depicted as a line structure using 2 parallel lines. C 1 is single bonded to C N on the upper right. C 2 is single bonded to C N on the lower right. Delta is written under the reaction arrow." />

Alkene carbons are sp2 hybridized and cannot have wedged or dashed bonds.

Careful. This molecule is not meso. There is no plane of symmetry.


Diene stereochemistry:

In the traditional orientation of the diene approaching the dienophile from the top, inner substituents on the diene are on the top face of the product cyclohexene, and outer substituents are on the bottom face.


Predict the major, organic product for the following reaction.

<img src="https://media.pearsoncmg.com/ph/esm/ecs_mullins_organic1e/msa/content/practice-test/img/Ch22_Q04_QT.jpg" alt="The figure illustrates a reaction in which the product has to be determined. The reaction contains two reactants. The first reactant has the following structure: A 1 N and 5 C heteronuclear alkene chain is depicted as a line structure using 5 zigzag lines. N occupies the second position. A double bond is present between C 3 and C 4. N is single bonded to C H 3 below in the form of a line. C 2 is double bonded to C H 2 on the lower right in the form of two parallel lines. The second reactant has the following structure: A 2-carbon alkene chain is depicted as a line structure using 2 parallel lines. Delta is written under the reaction arrow." />

General Features

Predict the products of the following proposed Diels–Alder reactions.

(b) <img src="https://lightcat-files.s3.amazonaws.com/problem_images/c806bef6629447fc-1670523321398.jpg" alt="" /><img class="fr-dib" src="https://lightcat-files.s3.amazonaws.com/problem_images/31e0e5f33bb93cfc-1677634573250.jpg" style="width: 300px;">

Predict the products of the following proposed Diels–Alder reactions.

(a) <img src="https://lightcat-files.s3.amazonaws.com/problem_images/6245d47a6e217c91-1670522990678.jpg" alt="" /><img class="fr-dib" src="https://lightcat-files.s3.amazonaws.com/problem_images/ddd70290aa189e72-1677634548946.jpg" style="width: 300px;">

The highly reactive triple bond of benzyne is a powerful dienophile. Predict the product of the Diels–Alder reaction of benzyne (from chlorobenzene and NaOH, heated) with cyclopentadiene.

Predict the major product for each proposed Diels–Alder reaction. Include stereochemistry where appropriate.

(a) <img src="https://lightcat-files.s3.amazonaws.com/problem_images/abb62fffc2f01bfd-1672664690220.jpg" alt="" />

The Diels-Alder reaction is a heat-catalyzed, reversible pericylic reaction between a conjugated 1,3-diene and a dienophile.&nbsp;

Predict the products of the following proposed Diels–Alder reactions. Include stereochemistry where appropriate.

(a) <img src="https://lightcat-files.s3.amazonaws.com/problem_images/37872c4d4b7922ea-1670947076824.jpg" alt="" /><img class="fr-dib" src="https://lightcat-files.s3.amazonaws.com/problem_images/5b90124f123123fd-1677634762988.jpg" style="width: 300px;">

Predict the products of the following Diels–Alder reactions.

(a) <img src="https://lightcat-files.s3.amazonaws.com/problem_images/b7b461d658a28d9f-1670429070453.jpg" alt="" /> 
(b) <img src="" alt="" /><img class="fr-dib" src="https://lightcat-files.s3.amazonaws.com/problem_images/d9a20e16c1a5e5ec-1677635074473.jpg" style="width: 599px;">

Predict the products of the following proposed Diels–Alder reactions. Include stereochemistry where appropriate.

(a) <img src="https://lightcat-files.s3.amazonaws.com/problem_images/a25dd105e8715a10-1670523899957.jpg" alt="" />
(b) <img src="" alt="" />
(c) <img src="" alt="" /> <img class="fr-dib" src="https://lightcat-files.s3.amazonaws.com/problem_images/d9c23b34f0e98258-1677634840843.jpg" style="width: 561px;">

Predict the products of the following proposed Diels–Alder reactions. Include stereochemistry where appropriate.

(d) <img src="https://lightcat-files.s3.amazonaws.com/problem_images/c703475583d747e5-1670578886047.jpg" alt="" /><img class="fr-dib" src="https://lightcat-files.s3.amazonaws.com/problem_images/b29e50aa13f72bf3-1677635305704.jpg" style="width: 258px;">

How would the following substituents affect the rate of a Diels–Alder reaction?

a. an electron-donating substituent in the diene

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Organic Chemistry

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Orbital Diagram:4-atoms- 1,3-butadiene

Allylic Halogenation

HOMO LUMO

Orbital Diagram:5-atoms- Allylic Ions

Drawing Atomic Orbitals

Cumulative Electrocyclic Problems

Congrats guys, we're almost to the end. But before we finish let's talk cumulatively about thermal and photochemical electrocyclic reactions.&nbsp;

Conjugated Hydrohalogenation (1,2 vs 1,4 addition)

Orbital Diagram:Excited States

Diels-Alder Forming Bridged Products

What happens when we add some&#160;complexity to our s-cis-1,3-diene? We can form a bridged diels-alder product. It&#39;s a lot easier than it sounds, I promise! Let&#39;s take a look.&#160;

Conjugation Chemistry

Thermal Electrocyclic Reactions

Thermal Cycloaddition Reactions

Photochemical Electrocyclic Reactions

Molecular Orbital Theory

Cope Rearrangement

Ready to learn a specific type of sigmatropic shift? The cope rearrangement can be differentiated from other pericyclic reactions due to its lack of conjugation.&#160;

Orbital Diagram:3-atoms- Allylic Ions

Sigmatropic Rearrangement

Here we will discuss an intramolecular pericyclic reaction in which 0 pi bonds are destroyed after a cyclic mechanism.&nbsp;

Claisen Rearrangement

Like the Cope rearrangment, Claisen can be differentiated from other pericyclic reactions due to its&#160;lack of conjugation as well. So how will we distinguish the two? Well, unlike Cope which uses only hydrocarbons, the Claisen Rearrangement utilizes a very specific functional group. Let&#39;s take a look.&#160;

Pericyclic Reaction

Photochemical Cycloaddition Reactions

Drawing Molecular Orbitals

Orbital Diagram:6-atoms- 1,3,5-hexatriene

Stability of Conjugated Intermediates

Diels-Alder Retrosynthesis

Imagine you are given the final cyclization product for a Diels-alder reaction and asked which diene and dienophile were required to make the 6-membered ring in the first place. What do you do?It turns out the process is a lot easier than you might think.&nbsp;&nbsp;

Predict the products of the following Diels–Alder reactions. (c) (d)

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Predict the products of the following Diels–Alder reactions. (c)
(d)