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ORGO > Week 4 Reactions > Flashcards

Week 4 Reactions Flashcards

1
Q

Halogenation

A

Cl2, AlCl3 OR Br2, FeBr3
————–> —————>

Ortho and para positions

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2
Q

Nitrogenation

A

HNO3, H2SO4
———————>

Meta position

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3
Q

Friedels-Crafts Alkylation

A

t-Butyl-Cl, AlCl3
———————->

t-Butyl, iPr, intramolecularly
NEW C-C BOND

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4
Q

Friedels-Crafts Acylation

A

Acid chloride, AlCl3
—————————->

R: only alkene FGs
NEW C-C BOND

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5
Q

SNAR

A

Nu:
—->

EWG ortho/para to LG
EWG often NO2 or ketone
Use OH-/OR- or SH-/SR- for synthesis

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6
Q

Ketone/aldehyde to 3* alcohol

A
  1. RMgBr, Et2O
    - ——————–>
  2. H+ wkup

Cannot use on acidic protons: deprotonate and reprotonate
Grignard Addition
NEW C-C BOND

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7
Q

Ketone/Aldehyde Reduction

Ketone/aldehyde to 2* alcohol

A

NaBH4, EtOH

——————->

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8
Q

Reversible Carbonyl Addition: Ketone/aldehyde to acetal

A

ROH, H+ cat.
——————>

Protonate, ROH attack, H+ transfer, LPP, ROH attack, sol

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9
Q

Reversible Carbonyl Addition: Ketone/aldehyde to hemiacetal

A

RO-, ROH
————–>

RO- attack, H-OR protonate

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10
Q

Reversible Carbonyl Addition: Ketone/aldehyde to cyanohydrin

A

NaCN, ROH
—————–>

CN- attack, H-OR protonate

Doesn’t work on esters or carb. acids (+ derivs).

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11
Q

Reversible Carbonyl Addition: Ketone/aldehyde to imine

A

RNH2, pH=5
——————>

Protonate, RNH2 attack, H+ transfer, LPP, sol

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12
Q

Reversible Carbonyl Addition: Ketone/aldehyde to enamine

A

R2NH, pH=5
——————>

Protonate, R2NH attack, H+ transfer, LPP, H+ mvmt to form double bond

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13
Q

Acetal Hydrolysis

A

H3O+
——–>

Protonate, LPP, H2O attack, H+ transfer, LPP, sol

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14
Q

Imine Hydrolysis

A

H3O+
——–>

Protonate, H2O attack, H+ transfer, LPP, sol

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15
Q

Enamine Hydrolysis

A

H3O+
——–>

LPP and protonate, H2O attack, H+ transfer, LPP, sol

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16
Q

Imine or enamine to 2* amine

A

H2, Pd/C
————->

Removing double bond and adding H
Imine Reduction

17
Q

Ketone/aldehyde to 2/3 amine

A

+ RNH2/R2NH NaBH3CN, pH=5
————————->

Protonate, RNH2/R2NH attack, H+ transfer, LPP, BH3CN attack (pushing double bond up/adding H)
Reductive Amination

18
Q

Wittig: Alkyl halide to ylide

A
  1. PPh3
    - ———->
  2. n-BuLi

SN2, deprotonate

19
Q

Wittig: Ylide to alkene

A

O
||
R R’
——–>

PPh3 LP attack, O LP to PPh3+, CP -> CO
Favors cis alkenes
NEW C=C BOND

20
Q

One-Step Carbonyl Reduction: Clemmensen

Aldehyde/ketone to bottom part of aldehyde/ketone (alkane)

A

Zn, HCl
———–>

Just “erase” C=O

21
Q

Grignard to carboxylic acid

A
  1. CO2
    - ——–>
  2. H+ wkup

R-MgBr attack C in O=C=O, H+ wkup to protonate O:-

22
Q

Transesterification

Ester with R to Ester with R”

A

ROH, H+
————>

Protonate, ROH attack, H+ transfer, LPP, sol

23
Q

Transesterification: Going backwards

A

RO-, ROH
————–>

RO- attack, LPP (old) OR’ off

24
Q

Carboxylic Acid Derivative Hydrolysis: Acid chloride to carboxylic acid

A

H2O
——->

H2O attack, LPP, sol

25
Q

Carboxylic Acid Derivative Hydrolysis: Amide to carboxylic acid

A

H2O, H+, heat
——————–>

Protonate, H2O attack, H+ transfer, LPP, sol

26
Q

Carboxylic Acid Derivative Hydrolysis: Ester to carboxylic acid

A
  1. OH-, H2O
    - —————>
  2. H+ wkup

OH- attack, LPP, deprotonate with H2O (or ROH), reprotonate with H+ wkup

27
Q

Carboxylic Acid Derivative Hydrolysis: Nitrile to carboxylic acid

A

H2O (2 equiv.), H+, heat
———————————->

Protonate, H2O attack, H+ transfer, LPP, sol

28
Q

Forming acid chloride

Carboxylic acid to acid chloride

A

SOCl2
———>

Attack SOCl2, Cl- attack, LPP, sol

29
Q

Reacting Acid Chlorides: Acid chloride to ester

A

ROH
——->

Cl replaced with OR

30
Q

Acid chloride to amide

A

RNH2
——–>
pyr

RNH2 attack, LPP, pyr (acting as sol)
For 1: NH3
For 2: RNH2
For 3*: R2NH

31
Q

Reduction of CADs: Ester to 1* alcohol

A
  1. LAH, Et2O
    - —————->
  2. H+ wkup

LAH attack, LPP, LAH, H+ wkup

LAH double addition (ester with LAH)

32
Q

Reduction of CADs: Carboxylic acid to 1* alcohol

A
  1. LAH, Et2O
    - —————->
  2. H+ wkup

LAH attack, H+ wkup

33
Q

Reduction of CADs: Amide to amine

A
  1. LAH, Et2O
    - —————->
  2. H+ wkup

Just “erase” C=O

34
Q

Reduction of CADs: Nitrile to 1* amine

A
  1. LAH, Et2O
    - —————->
  2. H+ wkup
35
Q

Acid chloride to 3* alcohol

A
  1. RMgBr
    - ————>
  2. H+ wkup

RMgBr attack, LPP, RMgBr attack, H+ wkup
Double addition of Grignards
2 NEW C-C BONDS

36
Q

Ester to 3* alcohol

A
  1. RMgBr
    - ————>
  2. H+ wkup

RMgBr attack, LPP, RMgBr attack, H+ wkup
Double addition of Grignards
2 NEW C-C BONDS

37
Q

Partial Reductions: Acid chloride to ketone

A

RZnBr
———>

RZnBr, LPP
“Zignard”
NEW C-C BOND

38
Q

Partial Reductions: Ester to aldehyde

A
  1. DIBAL-H, -78* C
    - ————————>
  2. H+ wkup

Attack DIBAL-H, OR LP to Al, H+ wkup

39
Q

Baeyer-Villiger Oxidation

Ketone to ester

A

mCPBA
———–>

Attack H on mCPBA, O:- on mCPBA attacks C=O, OH LP forms double bond and more substituted C-R attacks O on mCPBA, O:- attacks H on ester

BREAKS C-C AND ADDS O
Can expand rings

ORGO (12 decks)

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