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

Q

Acid chloride to primary alcohol

A

NaBH4, EtOH (aq)

Q

Primary alcohol to sulfonate ester

A

TsCl, pyridine

Q

Primary alcohol to primary bromoalkane

A

HBr (conc), reflux

Often eliminates

Q

Ether to primary alcohol

A

HI (conc) or HBr (conc), heat

Q

Carboxylic acid to primary alcohol

A

BH3

Q

Ester to primary alcohol

A

LiBH4

Q

Ester to amide

A

RNH2, pyridine

Q

Transesterification

A

ROH, heat, acid/base catalyst

Q

Sulfonate ester to alkene

A

tBuOK, EtOH

Q

Sulfonate ester nucleophilic substitution

A

Nu in DMSO/DMF

Q

Primary bromoalkane to ether

A

NaOMe, MeOH

Q

Primary bromoalkane to alkene

A

tBuOK, EtOH

Q

Primary bromoalkane nucleophilic substitution

A

Nu in DMSO/DMF

Q

Ketone to tertiary alcohol

A

i) RMgBr ii) H2O

Q

Tertiary alcohol to alkoxide

A

NaH

Q

Tertiary alcohol to tertiary bromoalkane

A

HBr (conc), reflux

Elimination not possible

Q

Tertiary alcohol to tertiary bromoalkane

A

HBr (conc), reflux

Elimination not possible

Q

Tertiary bromoalkane to tertiary alcohol

A

H2O, pyridine

Q

Tertiary bromoalkane to ether

A

ROH, pyridine

Q

Hydrogenation of alkenes

A

H2, Pd catalyst

Q

Alkene to tertiary bromoalkane

A

HBr (conc)

Q

Alkene to bromohydrin

A

Br2 (aq)

Q

Alkene to dibromoalkane

A

Br2, THF

Q

Alkene to alcohol

Anti-Markovnikov

A

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

Q

Alkene to epoxide

A

m-CPBA

Q

Epoxide opening

A

Nu

Q

Alkene to alcohol

Markovnikov

A

H2SO4 (aq, dil)