| Alcohol Type | Reagent | Product | Notes | |-------------|---------|---------|-------| | 1° Alcohol | K2Cr2O7/H2SO4 | Carboxylic acid | Overoxidation common | | 1° Alcohol | PCC, CH2Cl2 | Aldehyde | Mild, stops at aldehyde | | 2° Alcohol | CrO3/H2SO4 | Ketone | Jones oxidation | | 2° Alcohol | DMSO, (COCl)2, Et3N (Swern) | Ketone | No heavy metals, low temp | | 2° Alcohol | NaOCl, TEMPO (mild) | Ketone | Green chemistry method |
| Reagent | Typical Reaction | Product Type | |---------|----------------|---------------| | (Ozone) | Ozonolysis of alkenes | Carbonyl compounds | | NaNH2 | Alkyne deprotonation | Acetylide ions | | BH3·THF | Hydroboration-oxidation | Anti-Markovnikov alcohol | | LiAlH4 | Reduction of esters, acids, amides | Primary alcohols | | NaBH4 | Reduction of aldehydes, ketones | Alcohols (no esters) | | PCC | Oxidation of 1° alcohols | Aldehydes (not acids) | | m-CPBA | Epoxidation | Epoxides | | NBS (N-Bromosuccinimide) | Allylic bromination | Allylic bromides | Reactions And Reagents O.p Agarwal.pdf
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