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organic chemistry bsc > Mechanisms reagents and solvents > Flashcards

Mechanisms reagents and solvents Flashcards

1
Q

Ketone to cyanohydrin R&S

A

R = NaCN, H2SO4
S = water

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2
Q

Cyanohydrin to ketone R&S

A

R = NaOH acid catalyst
S = H2O

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3
Q

Ketone to secondary alcohol R&S

A

R = NaBH4
S = EtOH

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4
Q

Ketone to tertiary alcohol R&S

A

R = MeMgBr/ LiMe, H2O step 2 only
S = Et2O/ THF (aprotic)

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5
Q

ketone to hydrate R&S

A

R = H2O
S = H2O

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6
Q

Ketone to hemiacetal R&S (acidic and basic)

A

R = MeOH ( with either HCl/ NaOH)
S = MeOH

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7
Q

Hemiacetal to ketone R&S (acidic and basic)

A

R = H2O (with either HCl or NaOH)
S = H2O

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8
Q

Bisulfide addition of a ketone R&S

A

R = NaHSO3 (sodium bisulfite)
S = H2O

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9
Q

Hemiacetal to acetal R&S

A

R = MeOH (HCl catalyst needed to protonate leaving group)
S = THF

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10
Q

Acetal to ketone R&S

A

R = H2O (HCl catalyst)
S = THF

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11
Q

Acid chloride to ester R&S

A

R = EtOH and base eg pyridine
S = THF

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12
Q

Ester to carboxylic acid R&S (acidic and basic)

A

R = H2O (HCl or NaOH catalyst)
S = H2O

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13
Q

Acid chloride to acid anhydride R&S

A

R = sodium ethanoate
S = THF

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14
Q

Acid chloride to amide R&S

A

R = NH3
S = H2O

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15
Q

Amide to carboxylic acid R&S (acidic or basic)

A

R = H2O, Heat (HCl/NaOH cat )
S = H2O

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16
Q

Amide to amine R&S

A

R = LiAlH4
S = Et2O/ THF (aprotic)

17
Q

Carboxylic acid to acid chloride R&S (two possible reactions)

A

R = SOCl2
S = none
or
R = PCl5
S = THF

18
Q

Amide to ketone R&S

A

R = MeMgBr (H2O step 2 & HCl)
S = Et2O/THF

19
Q

Nitrile to ketone R&S

A

R = RMgBr acid catalyst
S = Et2O/THF

20
Q

Ketone to imine R&S

A

R = NH3 (HCl catalyst)
S = THF

21
Q

Ketone to alkene R&S

A

R = phosphonium ylide
S = Et2O (aprotic)

22
Q

Ketone to enol R&S

A

R = H2O (acid/ base catalyst)

23
Q

ketone to alkyl bromide R&S

A

R = Br2 and acetic acid AcOH

24
Q

Ketone to ketone with R group added R&S

A

step one
R = LDA
S = THF
step 2
R = R-I

25
Q

Aldehyde to aldol R&S

A

R = NaOH
S = H2O

organic chemistry bsc (5 decks)

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