Organic Synthesis Flashcards by Chloe Harris

What mechanism do alkanes undergo?

free radical substitution

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What mechanism do alkenes undergo?

electrophilic addition

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What mechanism do alcohols and haloalkanes undergo?

nucleophilic substitution

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alkane –> haloalkane

reagent: halogen
conditions: UV light
reaction: free radical substitution

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alkene –> alkane

reagent: H2(g)
conditions: Ni catalyst/423K (high temp)
reaction: addition/hydrogenation

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alkene –> haloalkane

reagent: halogen OR hydrogen halide
conditions: room temperature
reaction: electrophilic addition/halogenation

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alkene –> alcohol

reagent: H20(g)
conditions: H3PO4 catalyst
reaction: electrophilic addition/hydration

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1° alcohol –> aldehyde

reagent: K2Cr2O7
conditions: dilute H2SO4/heat and distil
reaction: oxidation

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1° alcohol –> carboxylic acid

reagent: K2Cr2O7
conditions: dilute H2SO4/heat under reflux
reaction: oxidation

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2° alcohol –> ketone

reagent: K2Cr2O7
conditions: dilute H2SO4/heat under reflux
reaction: oxidation

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alcohol –> alkene

conditions: conc H2SO4 or H3PO4 and heat
reaction: elimination/dehydration

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alcohol –> haloalkane

reagent: hydrogen halide made in situ
NaX + H2SO4 –> HX + NaHSO4
conditions: heat under reflux
reaction: nucleophilic substitution

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1° haloalkane –> alcohol

reagent: NaOH(aq) or H2O(aq)
reaction: nucleophilic substitution/hydrolysis (if water in used as a nucleophile)

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what mechanisms do aromatic compounds undergo?

electrophilic substitution

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2,4,6 directing groups

activating groups:
NH2
OH

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3,5 directing groups

deactivating groups:
NO2

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aldehyde –> 1° alcohol

reagents: NaBH4(aq)
reaction: nucleophilic addition

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ketone –> 2° alcohol

reagents: NaBH4(aq)
reaction: nucleophilic addition

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carbonyl –> hydroxynitrile

reagents: 2NaCN + H2SO4 –> 2HCN + Na2SO4 (in situ)
reaction: nucleophilic addition

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what reactions do carboxylic acids undergo?

redox (with metals)
neutralisation (with bases)
forms carboxylate ions and salts

carboxylic acid + metal

–> metal carboxylate + hydrogen

butanoic acid + Mg –> magnesium butanoate + H2

carboxylic acid + metal oxide

–> metal carboxylate + water

butanoic acid + CaO –> calcium butanoate + H2O

carboxylic acid + alkali

–> carboxylate salt + water

butanoic acid + NaOH –> sodium butanoate + H2O

carboxylic acid + metal carbonate

–> carboxylate salt + carbon dioxide + water

butanoic acid + MgCO3 –> magnesium butanoate + CO2 + H2O

carboxylic acid --> acid anhydride

two carboxylic acids undergo condensation reaction (one OH group removed and the H from the other OH group)

esterification

carboxylic acid + alcohol --> ester (alcohol-yl carboxylic acid-oate) heat under reflux with conc H2SO4

acid hydrolysis of esters

ester + water --> carboxylic acid + alcohol heat with a dilute aqueous acid

alkaline hydrolysis of esters

ester + alkali --> carboxylate salt + alcohol IRREVERSIBLE

carboxylic acid --> acyl chloride

carboxylic acid + SOCl2 (thionyl chloride) --> acyl chloride + SO2(g) + HCl(g) propanoic acid + SOCl2 --> propanoyl chloride (more reactive than carboxylic acids)

acyl chloride --> ester

acyl chloride + alcohol --> ester + HCl ethanoyl chloride + methanol --> methyl ethanoate + HCl

acyl chloride --> carboxylic acid

acyl chloride + water --> carboxylic acid + HCl ethanoyl chloride + water --> ethanoic acid + HCl

acyl chloride --> 1° amide

acyl chloride + ammonia --> primary amide + ammonium chloride ethanoyl chloride + 2NH3 --> ethanamide + NH4Cl (can form a 2° and 3° amide by reacting with 1° and 2° amines)

acid anhydride --> carboxylic acid

acid anhydride + alcohol --> carboxylic acid + ester

what can and can't be reduced back to an alcohol?

CAN: aldehyde/ketone CAN'T: carboxylic acid

what can and can't nitriles be turned into?

CAN: carboxylic acids/amines CAN'T: aldehydes/ketones

haloalkane --> amine

reagents: excess NH3 and ethanol conditions: heat reaction: nucelophilic substitution

haloalkane --> nitrile

reagents: CN- and ethanol reaction: nucleophilic substitution

nitrile/hydroxynitrile --> carboxylic acid

reagents: HCl(aq) conditions: heat DON'T FORGET (aq) AS WATER IS NEEDED

carbonyl --> hydroxynitrile

reagents: NaCN + H2SO4 (HCN in situation) reaction: nucleophilic addition

nitrile/hydroxynitrile --> carboxylic acid

reagents: H2 and Ni catalyst reaction: hydrogenation

acyl chloride --> carboxylic acid

reagents: H2O

benzene --> nitrobenzene

reagents: conc HNO3 + conc H2SO4 conditions: 50°C reaction: nitration/electrophilic substitution

benzene --> alkylbenzene

reagents: haloalkane + AlX3 reaction: alkylation/nucleophilic substitution

benzene --> halobenzene

reagents: halogen and AlX3 reaction: (2,4,6) electrophilic substitution

benzene --> phenylketone

reagents: acyl chloride + AlCl3 reaction: electrophilic substitution

nitrobenzene --> phenylamine

reagents: conc HCl and Sn catalyst reaction: electrophilic substitution

phenol --> nitrophenol

reagents: dilute HNO3 reaction: (2,4,6) electrophilic substitution

which aromatic compounds do and don't require a halogen carrier?

benzene DOES require a halogen carrier phenol DOESN'T require a halogen carrier