Reactions Flashcards by Teymour Taj

Q

Carboxylic acid to acyl chloride

A

SOCl2

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Q

Acyl chloride to carboxylic acid

A

H2O

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Q

Acyl chloride to carboxylic acid

A

H20

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Q

Carboxylic acid to ester

A

ROH, heat, acid catalyst

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Q

Ester to carboxylic acid

A

H2O, heat, acid/base catalyst

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Q

Acyl chloride to ketone

A

i) RMgBr (1eq) ii)H2O

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Q

Acid anhydride to ketone

A

i) RMgBr (1eq) ii) H2O

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Q

Ketone to hemiacetal

A

ROH, acid/base catalyst

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Q

Hemiacetal to acetal

A

ROH, acid catalyst

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Q

Ketone to secondary alcohol

A

NaBH4, EtOH (aq)

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Q

Tertiary alcohol to tertiary bromoalkane

A

HBr (conc), reflux

Often eliminates

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Q

Nucleophilic substitution on secondary bromoalkane

A

Nu in DMSO/DMF

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Q

Secondary bromoalkane to organolithium

A

Li, Et2O

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Q

Secondary bromoalkane to Grignard

A

Mg, Et2O

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Q

Secondary bromoalkane to nitrile

A

KCN, EtOH

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Q

Organolithium to carboxylic acid

A

i) CO2 ii) HCl, H2O

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Q

Grignard to carboxylic acid

A

i) CO2 ii) HCl, H2O

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Q

Nitrile to carboxylic acid

A

H2O, H2SO4, heat

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Q

Ketone to hydroxynitrile

A

i) NaCN ii) HCl (aq)

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Q

Acid chloride to anhydride

A

RCOONa, Et2O

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Q

Anhydride to primary alcohol

A

NaBH4, EtOH (aq)

Q

Anhydride to amide

A

RNH2, pyridine

Q

Amide to amine

A

i) LiAlH4 ii) H2O

Q

Acid chloride to amide

A

RNH2, pyridine

Acid chloride to primary alcohol

NaBH4, EtOH (aq)

Primary alcohol to sulfonate ester

TsCl, pyridine

Primary alcohol to primary bromoalkane

HBr (conc), reflux | Often eliminates

Ether to primary alcohol

HI (conc) _or_ HBr (conc), heat

Carboxylic acid to primary alcohol

BH3

Ester to primary alcohol

LiBH4

Ester to amide

RNH2, pyridine

Transesterification

ROH, heat, acid/base catalyst

Sulfonate ester to alkene

tBuOK, EtOH

Sulfonate ester nucleophilic substitution

Nu in DMSO/DMF

Primary bromoalkane to ether

NaOMe, MeOH

Primary bromoalkane to alkene

tBuOK, EtOH

Primary bromoalkane nucleophilic substitution

Nu in DMSO/DMF

Ketone to tertiary alcohol

i) RMgBr ii) H2O

Tertiary alcohol to alkoxide

NaH

Tertiary alcohol to tertiary bromoalkane

HBr (conc), reflux | Elimination not possible

Tertiary alcohol to tertiary bromoalkane

HBr (conc), reflux | Elimination not possible

Tertiary bromoalkane to tertiary alcohol

H2O, pyridine

Tertiary bromoalkane to ether

ROH, pyridine

Hydrogenation of alkenes

H2, Pd catalyst

Alkene to tertiary bromoalkane

HBr (conc)

Alkene to bromohydrin

Br2 (aq)

Alkene to dibromoalkane

Br2, THF

Alkene to alcohol | Anti-Markovnikov

i) BH3, THF ii) H2O2, NaOH, H2O

Alkene to epoxide

m-CPBA

Epoxide opening

Nu

Alkene to alcohol | Markovnikov

H2SO4 (aq, dil)