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Organic Chemistry 有機化学 基本の反応機構

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更新日期:2018-04-01

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Organic Chemistry 有機化学 基本の反応機構(圖1)-速報App

Organic Chemistry Reaction Mechanism is a useful App for learning the fundamentals of reaction mechanism in organic chemistry by using curved arrows. Mastering basic reaction mechanisms is an important survival skill for students learning organic chemistry.

Table of Contents (Total 106 videos)

1. Types of arrows used in organic chemistry

2. Basic principles in organic chemistry

3. Resonance

4. Halogenation of alkanes (Radical reaction)

5. Alkene addition reactions: Electrophilic additions 5-1. Addition of hydrogen halide

5-2. Stability of carbocations

5-3. Supplementary: Rearrangement reaction

5-4. Acid catalyzed addition of water (Hydration)

5-4. Reaction mechanism (How to draw curved arrows)

5-5. Oxymercuration

5-6. Hydroboration

5-7. Addition of halogen (Halogenation): Bromination

5-8. Reaction with peroxyacid (peracid): Epoxidation 5-9. Reaction with osmium tetroxide: Dihydroxidation

5-10. Reaction with ozone: Ozonolysis

5-11. Reaction with hydrogen (Catalytic hydrogenation)

6. Alkyne addition reactions: Electrophilic addition 6-1. Addition of hydrogen halide

6-2. Addition of water

6-3. Addition of halogen (Bromination) 6-4. Addition of hydrogen: Half reduction

6-5. Supplementary: Birch reduction

7. Electrophilic aromatic substitution 7-1. Nitration

7-2. Bromination

7-3. Sulfonation: Sulfonation is reversible !

7-4. Friedel-Crafts reactions 7-4. (A) Friedel-Crafts alkylation

7-4. (B) Friedel-Crafts acylation

7-5. Summary of electrophilic aromatic substitution

7-6. Electrophilic substitution of benzene derivatives 7-6-1. Reactivity

7-6-2. Orientation

7-7. Theory of orientation 7-7-1. Toluene: o,p-directing and activating

7-7-2. Phenol: o,p-directing and activating

7-7-3. Nitrobenzene: m-directing and deactivating

8. Nucleophilic substitution (SN2 and SN1) of alkyl halides 8-1. SN2 reaction

8-2. Reaction mechanism of SN2

8-3. SN1 reaction

8-4. Reaction mechanism of SN1

9. Elimination reaction (E2 and E1) of alkyl halides 9-1. E2 reaction

9-2. Reaction mechanism of E2

9-3. E1 reaction

Organic Chemistry 有機化学 基本の反応機構(圖2)-速報App

9-4. Reaction mechanism of E1

10. Reaction of alcohols 10-1. Protonation with strong acids

10-2. Acid-catalyzed elimination of water (Dehydration)

10-3. Reaction with hydrogen halides

10-4. Reaction of allylic alcohols

10-5. Supplementary: Allyllic rearrangement

10-6. Supplementary: Saytzeff’s rule (Zaitsev’s rule)

11. Ethers: Synthesis and Reactions 11-1. Synthesis of ethers-1 11-2. Synthesis of ethers-2: Williamson Ether Synthesis

11-3. Acid cleavage of ethers: Reaction with acids

11-4. Supplementary: Removal of methyl protecting group

11-5. Nucleophilic opening of epoxides with Grignard reagents

12. Nucleophilic addition to carbonyl group (aldehydes and ketones) 12-1. The polarity of the C=O double bond

12-2. Nucleophilic addition to carbonyl group

12-3. Addition of alcohols: Hemiacetal and acetal formation

12-4. Addition of primary amines: Imine formation

12-5. Addition of Grignard reagents

12-6. Supplementary: Addition of Grignard reagents to carbon dioxide

12-7. Addition of acetylides

12-8. Addition of hydrogen cyanide

12-9. Reduction of ketones and aldehydes

13. Esters: Synthesis and Reactions 13-1. Synthetic method for esters-1: Fischer esterification

13-2. Synthetic method for esters-2: Methyl ester formation by diazomethane

13-3. Hydrolysis of esters

13-4. Supplementary: Acid-catalyzed hydrolysis of tert-butyl esters

13-5. Reaction with Grignard reagents

13-6. Reduction of esters

13-7. Alcoholysis of esters 13-8. Ammonolysis of esters

14. Enol and Enolate reactions (aldehydes and ketones) 14-1. Keto-enol equilibrium

14-2. Why are a-Hydrogens acidic ?

14-3. Enolization

14-4. Aldol reaction

14-5. Aldol condensation

14-6. E1cB reaction

15. Enolate reactions in esters 15-1. Claisen condensation

15-2. Dieckmann condensation and retro-Claisen condensation

15-3. Synthetic methods related to Claisen condensation

15-4. Acetoacetic ester synthesis

15-5. Malonic ester synthesis

16. Michael addition

Organic Chemistry 有機化学 基本の反応機構(圖3)-速報App

17. Robinson annulation

Organic Chemistry 有機化学 基本の反応機構(圖4)-速報App

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