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Mindmap-Galerie Organic Chemistry-Alcohol Mind Map
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Organic Chemistry-Alcohol Mind Map
Organic Chemistry-Alcohol Mind Map, the specific content includes physical properties, acidity, alkalinity, nucleophilicity, substitution reaction, E1 elimination reaction, oxidation reaction, dehydrogenation reaction, reaction and preparation of vicinal diols
Bearbeitet um 2023-03-20 16:15:42
Organic Chemistry-Alcohol Mind Map
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alcohol
physical properties
State: Lower alcohol is liquid, higher alcohol is solid
Solubility: Lower monohydric alcohols (1-3 carbons) form hydrogen bonds with water and are miscible with water in any ratio. All carbons 4-11 except tert-butyl alcohol are insoluble in water.
Density: Denser than alkanes but less than water
Boiling point: higher than alkanes with the same carbon number
Alcoholate: crystalline alcohol, many inorganic salts cannot dry alcohol
Acidic
React with metals
Comparison of acidity strength: 1° alcohol > 2° alcohol > 3° alcohol (compare the stability of negative ions after removing H) 1° alcohol has strong solvation effect, more dispersed charges, and strong acidity
alkaline
3° alcohol > 2° alcohol > 1° alcohol, the more electron-donating groups, the stronger the alkalinity
nucleophilicity
Reaction of alcohols with oxygenated inorganic acids
Reaction of alcohols with acid halides and acid anhydrides
Substitution reaction
Reaction of alcohol and HX
1°Alcohol-Sn2 reaction
2°Alcohol-Sn1 reaction (rearrangement reaction)
3°Alcohol - elimination reaction
Comparison of reactivity: allyl type, benzylic type>3° alcohol>2° alcohol>1° alcohol
Neighbor group participation (intramolecular reaction)
get enantiomers
Reacts with phosphorus halide
1°Alcohol-Sn2 reaction
2° alcohol, 3° alcohol - Sn1 reaction
reacts with thionyl chloride
Neutral - configuration maintained (diethyl ether, 1,4-dioxane)
Basic - configuration flip (pyridine)
Reaction with benzenesulfonyl chloride
The configuration is maintained in the first step, and the configuration is flipped in the second step (mainly 1° and 2°)
E1 elimination response
intramolecular dehydration
Follow Zaitsev's rules
There are cis and trans isomers, mainly E type
rearrangement reaction
intermolecular dehydration
oxidation reaction
KMnO4
1° Oxidation of alcohol to acid
2° Alcohol is oxidized to ketone, which can easily further break C-C bonds to form small molecular compounds.
3°Alcohol is eliminated to become an alkene and then oxidized
HNO3
1° Oxidation of alcohol to acid
2° alcohol and 3° alcohol are oxidized in concentrated nitric acid and break the C-C bonds to form small molecular compounds.
Cyclic Alcohol
C-C cleavage forms dibasic acid
MnO2
Oxidation of hydroxyl groups at allyl and benzyl positions to aldehydes or ketones
Chromic acid
Sodium dichromate
1°Alcohol - first oxidized to aldehyde, and then into acid. To obtain the aldehyde, it needs to be separated in time.
2°Alcohol - oxidized to ketone, ketone has certain resistance
Sarit reagent (CrO3 pyridine)
1° Oxidation of alcohol to aldehyde
2° Oxidation of alcohol to ketone
Jones reagent (CrO3 dilute sulfuric acid)
1° Oxidation of alcohol to aldehyde
2° Oxidation of alcohol to ketone
Ofenol oxidation method
Mainly used for 2° alcohol, 1° alcohol is prone to aldol condensation.
Alcohols are oxidized to ketones and ketones are reduced to alcohols
Fitzner-Moffat reaction
Dimethyl sulfoxide and dicyclohexylcarbodiimide (DCC)
Aldehydes can be obtained from 1° alcohol with high yields
dehydrogenation reaction
CuCrO4
Pd-C
alcohol to aldehyde ketone
Reaction of vicinal diol
Oxidation
Periodic acid H5IO6
Generate aldehydes, ketones, acids
Cyclic intermediate mechanism
The cis form has a fast rate, the trans form can be converted to the e bond, and the ortho cross reaction has a slow rate, but large groups cannot be located in the a bond.
Lead tetraacetate Pb(OAc)4
Cyclic intermediate mechanism
Pyridine is used as the reaction solvent to speed up the reaction rate and does not require intermediates.
Alpha-hydroxy aldehydes or ketones, alpha-hydroxy acids, and 1,2-diones require the presence of a small amount of water to react
The cis form has a fast rate, the trans form can be converted to the e bond, and the ortho cross reaction has a slow rate, but large groups cannot be located in the a bond.
pinacol rearrangement
Stability of carbocation
Migration ability of groups
The migration group and the leaving group are coplanar in trans form at a fast rate, and are prone to ring contraction (e bond) or epoxy generation (a bond) if they are not in trans form.
preparation
Hydrolysis of alkyl halide
Hydration, hydroboration and hydroxymercuryation of olefins
reduction of carbonyl compounds
format reagent
Reaction with epoxy
Acidic conditions: attack the more substituted end, and the carbocation is stable
Alkaline conditions: attack the end with smaller steric resistance
produces an alcohol with two more carbons
reaction with aldehydes and ketones
Reaction with carboxylic acid derivatives
Reacts with formate to form symmetric 2° alcohol
Reacts with carboxylic acid ester to form 3° alcohol containing two identical hydrocarbon groups