Overview of Organic Chemistry

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Organic chemistry Chemistry of carbon compounds >95% of all known compounds contain

carbon Biological system, materials, clothing, medicine,

petroleum… Structure, mechanism, synthesis

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電子軌域 電子雲

Exer Biochem c0-organic chem 4Sigma-bonding 單鍵covalent bonding 共價鍵

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Pi-bonding 雙鍵 三鍵

Exer Biochem c0-organic chem 6Ionic bonding 離子鍵正負電的結合

Exer Biochem c0-organic chem 7Covalent bonding 共價鍵共用電子

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How to determine valence 價數 Number of electrons in orbital

2 (s), 8 (sp3), 8 (sp3)

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Number of bonds and structure

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Easier way: omit C, H

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3D structure on 2D

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Cyclic structures

六元環

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Cyclohexane structure

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Stereoisomer 空間異構物 Carbons with 4 different groups attached 不對稱碳 不對稱

中心 Chiral compounds 對掌異構物 Very common in biological compounds

With different biological functions/activities R/S: rank attached groups from heaviest to smallest No relation with d/l or +/-, determined experimentally

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Chirality of Amino Acids

Comparison of the stereochemistry of alanine and glyceraldehyde (Fischer projection formulas)

H NH3+

COO-

CH3

+H3N H

COO-

CH3

D-Alanine L-Alanine

H OH

CHO

CH2OH

HO H

CHO

CH2OH

D-Glyceraldehyde L-Glyceraldehyde

the naturally occurring form

the naturally occurring form

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Alkene: easy to react

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Benzene 苯

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Alcohols

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Alcohol, aldehyde, carboxylic acidreduction 還原 : addition of H, loss of O

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Alcohol, aldehyde, carboxylic acidoxidation 氧化 : loss of H, addition of O

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Aldehyde and ketone

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Aldehyde and ketone

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Carbohydrate structure 同分異構物

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Exer Biochem c0-organic chem 37Carboxylic acidacetic acid acetate

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Ester: acid + alcohol

↑nucleophile

Exer Biochem c0-organic chem 40Fat: triacyl glycerol, triglyceride三酸甘油酯

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Lactone 內酯

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Ring form of CHO: a lactone

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Exer Biochem c0-organic chem 47Electrophilic: love electron (-) nucleophilic: love nucleus (+)

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Typical electrophiles

Exer Biochem c0-organic chem 49Predict reactionsnucleophilic attack

Basic structure of amino acids

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Peptide bond

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Exer Biochem c0-organic chem 53Cysteine and cystinedisulfide bond 雙硫鍵