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Total Synthesis > Reactions > Flashcards

Reactions Flashcards

1
Q

Aldol Reaction

A

two carbonyls to a,b-unsaturated ketone

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2
Q

Pinacol Coupling

A

2 carbonyls reacts with Mg to couple, forming diol, rearranges to ketone

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3
Q

Enolate Alkylation

A

enolate reacts with electrophile by sn2

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4
Q

alcohol dehydration

A

alcohol to alkene, generally most stable with shifts

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5
Q

barton deoxygenation

A

alcohol to alkane via radicals

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6
Q

Radical Dehalogenation

A

alkyl halide to alkane via radicals

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7
Q

Clemmenson Reduction

A

carbonyl to methylene with Zn(Hg) and H+

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8
Q

Wollf-Kishner

A

Carbonyl to methylene under base with H2NNH2

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9
Q

Michael Reaction

A

enolate reacts with a,b-unsaturated carbonyl to form 1,5 carbonyl

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10
Q

Ozonolysis

A

split alkene into symmetrical carbonyls

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11
Q

Stetter Reaction

A

1,4 addition of aldehyde to a,b-unsaturated carbonyl wiht NEt3

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12
Q

O-allylation

A

oxygen anion acts as nucleophile in sn2

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13
Q

Friedel Crafts Alkylation

A

benzene reacts with alkylhalide by lewis acid activation

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14
Q

Friedel Crafts Acylation

A

benzene reacts with acid chloride by lewis acid activation

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15
Q

Ether Formation

A

alcohol reacts with alkyl halide in presence of base

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16
Q

acetal formation

A

carbonyl reacts with alcohol (once to hemi, twice to acetal)

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17
Q

alkene metathesis

A

exchange substituents of two alkenes by catalysis

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18
Q

Wittig Olefination

A

Carbonyl reacts with phosphonium ylide to form alkene

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19
Q

Epoxidation

A

alkene reacts with m-CPBA stereoselectively

20
Q

Alkene addition

A

add electrophilie/nucleophile to alkene

21
Q

robinson annulation

A

michael addition followed by intramolecular aldol to form a,b unsaturated carbonyl cyclohexene

22
Q

Mozingo Reduction

A

carbonyl to methylene via thioketal

23
Q

Simmons Smith

A

cyclopropanation of alkene with Zn(Cu) and CH2I2

24
Q

Diekmann Reaction

A

Intramolecular claissen

25
Q

Alkyne Alkylation

A

Deprotonate alkyne to act as nucleophile in Sn2

26
Q

Gem diol

A

react carbonyl with water and vice versa

27
Q

Amine synthesis

A

reduction of amides, reduction of nitriles, hydrogenation of nitros, reduction of azides, reaction with alkyl halides, reduction of imines/enamines

28
Q

Carboxylic Acid Synth

A

oxidation of alcohols/aldehydes, gridnard addition to CO2

29
Q

Fischer Esterification

A

carboxylic acid with alcohol

30
Q

acid chloride synth

A

carboxylic acid with SOCl2

31
Q

amide synth

A

acid chloride and amine (Sn2)

32
Q

anhydride synth

A

acid chloride and carboxylate anion

33
Q

Villsmer Haack Formylation

A

Pyridine reacts with POCl3 and water to add aldehyde

34
Q

Organocopper reactions

A

reacts with alkyl halides, acyl halides, epoxides and a,b-unsaturated carbonyls to add alkyl group

35
Q

Weinreb amides

A

react with grignards to form ketones

36
Q

Wadsworth Emmons Olefination

A

Forms trans alkenes from phosphonium substrate

37
Q

Nitrile/azide synth

A

react alkyl halide with NaCN/N3

38
Q

Imine/enamine Synth

A

react carbonyl with amine

39
Q

Dihydroxylation

A

react alkene with OsO4 to add diol

40
Q

Hydrolysis of nitriles

A

goes to carboxylic acids

41
Q

Decarboxylation

A

eliminates CO2 from dicarbonyl

42
Q

Mannich Reaction

A

carbonyl reacts with amine and formaldehyde to form b-amino carbonyl

43
Q

Wohl Zeigler Reaction

A

adds bromine adjacent alkene via NBS radical

44
Q

Fischer Indole Synthesis

A

reaction of C6H6NHNH2 and aldehyde ketone to form indole

45
Q

Claisen Johnson Rearrangement

A

allylic alcohol reacts with trialkyl ether to produce a 1,6 unsaturated carbonyl ester.

46
Q

Eltrophilic aromatic substitution

A

benzene reacts with activated electrophiles such as halides, nitric acid, sulfonic acid, alkyls, acyls

47
Q

allylic oxidation

A

subbed alkene reacts with SeO2 to form allylic alcohol

Total Synthesis (2 decks)

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