Organic Roadmaps

15
7/21/2019 Organic Roadmaps http://slidepdf.com/reader/full/organic-roadmaps 1/15 alcohols    X    2    (    B    )    X    2    /    H    2    O     (    B    ) 1) BH 3  , 2) H 2 O 2  , NaOH (C, D) 1) Hg(OAc) 2  , H 2 O, 2) NaBH 4  , (A) H 3 O +  /H 2 O (A)    H    X    (    A    ) H 2  /Pd, Pt,or Ni (D) vicinal dihaloalkanes halohydrins 1) OsO 4  (D)  , 2) NaHSO 3 vicinal diols aldehydes/ ketones alkenes alkanes 1) O 3  , 2) (CH 3 ) 2 S haloakanes ROADMAP FOR REACTIONS Chapter 6 Reactions that cleave carbon-carbon bonds are indicated by reagents that are circled. (A) (B) (C) (D) (E) (F) (G) (H) (I) (J) (K)  (L) (M) (N) (O) Regiochemistry: Markovnikov addition to a  bond Stereochemistry: anti-addition Regiochemistry: non-Markovnikov addition to a  bond Stereochemistry: syn-addition Works well for methyl and 1° haloalkanes Stereochemistry: gives cis -alkenes as products Stereochemistry: gives trans -alkenes as products Reactivity of C–H bonds follows 3° > 2° > 1° Works for methyl, 1°, and 2° haloalkanes Works for 2° and 3° haloalkanes, may see rearrangements Works for all haloalkanes except methyl, although a bulky (non-nucleophilic) base must be used for 1° haloalkanes. Regiochemistry: follows Zaitzev’s rules so the more substituted alkene predominates. Stereochemistry: requirement for the X and H to be eliminated with anti-periplanar geometry. PBr 3  and SOX 2  works for methyl, 1°, and 2° haloalk anes. HX can give rearrangements. For 1° alcohols For 2° alcohols Regiochemistry: the product with the more substituted alkene predominates

description

Roadmaps for organic reactions.

Transcript of Organic Roadmaps

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alcohols

   X   2

   (   B   )

   X   2   /   H   2   O    (   B

   )

1) BH3 , 2) H2O2 , NaOH (C, D)

1) Hg(OAc)2 , H2O, 2) NaBH4 , (A)

H3O+ /H2O (A)

   H   X   (   A   )

H2 /Pd, Pt,or Ni (D)

vicinaldihaloalkanes

halohydrins

1) OsO4 (D) , 2) NaHSO3 vicinaldiols

aldehydes/ ketones

alkenesalkanes

1) O3 , 2) (CH3)2S

haloakanes

ROADMAP FOR REACTIONS Chapter 6

Reactions that cleave carbon-carbon 

bonds are indicated by reagents 

that are circled.

(A)

(B)

(C)

(D)

(E)

(F)

(G)(H)

( I )

(J)

(K)

 

(L)

(M)

(N)

(O)

Regiochemistry: Markovnikov addition to a  bond

Stereochemistry: anti-addition

Regiochemistry: non-Markovnikov addition to a  bond

Stereochemistry: syn-addition

Works well for methyl and 1° haloalkanes

Stereochemistry: gives cis -alkenes as products

Stereochemistry: gives trans -alkenes as productsReactivity of C–H bonds follows 3° > 2° > 1°

Works for methyl, 1°, and 2° haloalkanes

Works for 2° and 3° haloalkanes, may see rearrangements

Works for all haloalkanes except methyl, although a bulky

(non-nucleophilic) base must be used for 1° haloalkanes.

Regiochemistry: follows Zaitzev’s rules so the more substituted

alkene predominates. Stereochemistry: requirement for the

X and H to be eliminated with anti-periplanar geometry.

PBr3 and SOX2 works for methyl, 1°, and 2° haloalkanes.

HX can give rearrangements.

For 1° alcohols

For 2° alcohols

Regiochemistry: the product with the more

substituted alkene predominates

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Chapter 6Key:

Carbon-carbon bond forming 

reactions are indicated by reagents 

written with solid backgrounds 

and white lettering.

Reactions that cleave carbon-carbon 

bonds are indicated by reagents that are circled.

Chapter 7

ROADMAP FOR REACTIONS Chapters 6 7

alcohols

     N      a     N     H      2

           /     N     H   3

     N      a

            /     N     H   3

    (    G   )

2X2 1) (sia)2BH, 2) H2O

2, NaOH (C) 

1) BH3, 2) H2O

2, NaOH 

H2SO4, HgSO4 (A) 

HX (A)

     H      2

           /      L           i    n      d           l      a   r     C      a          t .

   (   F   )

     H      2

           /      P      d ,

      P          t ,

     N           i

vicinaldihaloalk anes

halohydrins

vicinaldiols

geminal

dihaloalk anes

vicinaltetr

ahaloa

lk anes

aldehydes / k etones

alk enes

alk anes

     C     R

        (        E        )

     N      a     C

alk ynes

haloak anes

      X      2

   (   B   )

      X      2

           /     H      2     O

    (   B   )

1) BH3, 2) H2O2, NaOH (C, D)

1) Hg(OAc)2, H2O, 2) NaBH4, (A)

H3O+ / H2O (A)

     H      X

    (   A   )

H2 / Pd, Pt,or Ni (D)

1) OsO4 (D), 2) NaHSO3

1)O3, 2) (CH3)2S

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allylichalides

alcohols

   R   C

   N  a   N   H   2   /   N   H   3

   N  a   /   N   H   3

       (        G       )

2X2 1) (sia)2BH, 2) H2O2 , NaOH (C) 

1) BH3 , 2) H2O2 , NaOH

H2SO4 , HgSO4 (A) 

HX (A)

   H   2   /   L   i  n   d   l  a  r   C  a   t .       (       F       )

   H   2   /   P   d ,   P   t ,   N   i

   X   2

       (       B       )

   X   2   /   H   2   O        (       B

       )

1) BH3 , 2) H2O2 , NaOH (C, D)

1) Hg(OAc)2 , H2O, 2) NaBH4 , (A)

H3O+ /H2O (A)

X2 , hv or heat (H)

   H   X       (       A       )

H2 /Pd, Pt,or Ni (D)

   H   B  r ,  p  e  r  o  x   i   d  e  s       (        C       )

NBS (O)

Chapter 6

Key:

Carbon-carbon bond forming 

reactions are indicated by reagents 

written with solid backgrounds 

and white lettering.

Reactions that cleave carbon-carbon 

bonds are indicated by reagents that are circled.

Chapter 7

Chapter 8

vicinaldihaloalkanes

halohydrins

1) OsO4 (D) , 2) NaHSO3 vicinaldiols

geminal

dihaloalkanes

vicinal

tetrahaloalkanes

aldehydes/ ketones

alkenesalkanes

   C   R

        (        E        )

   N  a   C

alkynes

1) O3 , 2) (CH3)2S

haloakanes

ROADMAP FOR REACTIONS Chapters 6 7 8

(A)

(B)

(C)

(D)

(E)

(F)

(G)(H)

( I )

(J)

(K)

 

(L)

(M)

(N)

(O)

Regiochemistry: Markovnikov addition to a  bond

Stereochemistry: anti-addition

Regiochemistry: non-Markovnikov addition to a  bond

Stereochemistry: syn-addition

Works well for methyl and 1° haloalkanes

Stereochemistry: gives cis -alkenes as products

Stereochemistry: gives trans -alkenes as productsReactivity of C–H bonds follows 3° > 2° > 1°

Works for methyl, 1°, and 2° haloalkanes

Works for 2° and 3° haloalkanes, may see rearrangements

Works for all haloalkanes except methyl, although a bulky

(non-nucleophilic) base must be used for 1° haloalkanes.

Regiochemistry: follows Zaitzev’s rules so the more substituted

alkene predominates. Stereochemistry: requirement for the

X and H to be eliminated with anti-periplanar geometry.

PBr3 and SOX2 works for methyl, 1°, and 2° haloalkanes.

HX can give rearrangements.

For 1° alcohols

For 2° alcohols

Regiochemistry: the product with the more substituted alkene

predominates

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allylichalides

alcohols

   N  a   C   N

    (   I   )

   C   L   i    (   E   )

   R   C

   N  a   H   R   2   (   I   )

   N  a   N   3   (   I   )

   N  a   S   R   (   I   )

   N  a   S   H    (

   I   )

   N  a   O   H    (   E

   )

   H   2   O ,  a  c   i   d   (   J   )

   N  a   O   R   (   E   )

   H   O   R ,  a  c   i   d   (   J   )

   N  a   N   H   2   /   N   H   3

   N  a   /   N   H   3   (    G   )

2X2 1) (sia)2BH, 2) H2O2 , NaOH (C)

1) BH3 , 2) H2O2 , NaOH

H2SO4 , HgSO4 (A) 

HX (A)

   H   2   /   L   i  n   d   l  a  r   C  a   t .   (   F   )

   H   2   /   P   d ,   P   t ,   N   i

   X   2   (   B   )

   X   2   /   H   2   O    (   B

   )

1) BH3 , 2) H2O2 , NaOH (C, D)

1) Hg(OAc)2 , H2O, 2) NaBH4 , (A)

H3O+ /H2O (A)

X2 , hv or heat (H)

   H   X   (   A   )

H2 /Pd, Pt,or Ni (D)

   N  a   O   R   (   K   )

   H   B  r ,  p  e  r  o  x   i   d  e  s   (    C   )

NBS (O)

Chapter 6

Key:

Carbon-carbon bond forming 

reactions are indicated by reagents 

written with solid backgrounds 

and white lettering.

Reactions that cleave carbon-carbon 

bonds are indicated by reagents that are circled.

Chapter 7

Chapter 8

Chapter 9

vicinaldihaloalkanes

halohydrins

1) OsO4 (D) , 2) NaHSO3 vicinaldiols

geminal

dihaloalkanes

vicinal

tetrahaloalkanes

aldehydes/ ketones

alkenes

alkylazides

aminesnitriles thioethersthiols

alkanes

   C   R

   (   E   )

   N  a   C

alkynes

1) O3 , 2) (CH3)2S

haloakanes

ethers

ROADMAP FOR REACTIONS Chapters 6 7 8 9

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allylichalides

alcohols

   N  a

   C   N

         (        I        )

   C   L   i         (        E        )

   R   C

   N  a

   H   R

   2

                   (

    I

                   )

   N  a

   N   3

                   (

    I

                   )

   N  a

   S   R

                   (

    I

                   )

   N  a

   S   H

                    (

    I

                   )

   N  a

   O   H

                    (         E                   )

   H   2

   O ,

  a  c

   i   d                   (         J                   )

   N  a

   O   R                   (         E                   )

   H   O   R

 ,  a  c

   i   d                   (         J                   )

   N  a

   N   H

   2   /   N   H

   3

   N  a

   /   N   H

   3                   (         G                   )

   H   2

   C  r   O

   4                   (          N                   )

   H   I   O

   4

   H   X

  o  r

   P   B  r   3  o  r

   S   O   C   l   2                   (          L                   )

H3PO4

   H   2

   C  r   O   4

   P   C   C                   (      M                   )

2X2 1) (sia)2BH, 2) H2O2 , NaOH (C) 

1) BH3 , 2) H2O2 , NaOH

H2SO4 , HgSO4 (A) 

HX (A)

   H   2

   /   L   i  n   d   l  a  r

   C  a

   t .                   (           F                   )

   H   2

   /   P   d

 ,   P   t ,   N   i

   X   2

                   (         B                   )

   X   2

   /   H   2

   O                    (

         B                   )

1) BH3 , 2) H2O2 , NaOH (C, D)

1) Hg(OAc)2 , H2O, 2) NaBH4 , (A)

H3O+ /H2O (A)

X2 , hv or heat (H)

   H   X                   (      A                   )

H2 /Pd, Pt,or Ni (D)

   N  a

   O   R                   (      K                   )

   H   B  r ,  p  e  r  o  x

   i   d  e  s                   (         C                   )

NBS (O)

Chapter 6

Key:

Carbon-carbon bond forming 

reactions are indicated by reagents 

written with solid backgrounds

and white lettering.

Reactions that cleave carbon-carbon 

bonds are indicated by reagents 

that are circled.

Chapter 7

Chapter 8

Chapter 9

Chapter 10

vicinaldihaloalkanes

halohydrins

1) OsO4 (D) , 2) NaHSO3 vicinaldiols

carboxylicacids

geminal

dihaloalkanes

vicinal

tetrahaloalkanes

aldehydes/ ketones

alkenes

alkylazides

aminesnitriles thioethersthiols

alkanes

   C   R        (        E        )

   N  a

   C

alkynes

1) O3 , 2) (CH3)2S

haloakanes

ethers

ROADMAP FOR REACTIONS Chapters 6 7 8 9 10

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Chapter 6

Key:

C a r b o n - c a r b o n  b o nd  f o r m i ng 

r ea c t i o ns  a r e  i nd i c a t e d  b  y  r ea g e n t s 

w r i tt e n  w i t h  s o li d  b a c k g r o unds  

a nd  w h i t e  l e tt e r i ng .

R ea c t i o ns  t h a t  c l ea v e  c a r b o n - c a r b o n 

b o nds  a r e  i 

nd i c a t e 

d  

b  y  r ea 

g e n 

t s 

t h a t  a r e  c i r c l e d .

Chapter 7

Chapter 8

Chapter 9

Chapter 10

Chapter 11

ROADMAP FOR REACTIONS Chapters 6 7 8 9 10 11

allylic

halides

alcohols

     N     a     C     N

                 (

                           I

                )

     C      L           i

                 (          E                )

     R     C

     N     a    H     R      2

                   (

    I

                   )

     N     a     N   3

                   (

    I

                   )

     N     a       S     R                   (

    I

                   )

     N     a       S    H                   (

    I

                   )

     N     a    O    H                   (         E                   )

    H      2    O ,     a  c           i      d                    (

         J                   )

     N     a    O     R

                   (         E                   )

    H

    O     R ,     a  c           i      d                    (

         J                   )

     N     a     N    H      2

           /     N    H   3

     N     a

           /     N    H   3

                   (         G                   )

    H      2     C   r    O

   4

                   (          N                   )

    H     I    O

   4

    H      X 

     o   r      P   B   r   3     o   r       S    O     C           l      2

                   (          L                   )

H3PO4

    H      2     C   r    O   4

      P     C     C

                   (      M                   )

2X2 1) (sia)2BH, 2) H2O

2, NaOH (C) 

1) BH3, 2) H2O

2, NaOH 

H2SO4, HgSO4 (A) 

HX (A)

    H      2

           /      L           i    n      d           l     a   r     C     a          t .

                   (           F                   )

    H      2

           /      P      d ,

      P          t ,

     N           i

      X      2

                   (         B                   )

      X      2

           /    H      2    O                   (         B                   )

1) BH3, 2) H2O2, NaOH (C, D)

1)Hg(OAc)2, H2O, 2) NaBH4, (A)

H3O+ / H2O (A)

H3O+ / H2O

X2, hv or heat (H)

    H      X

                    (      A                   )

H2 / Pd, Pt,or Ni (D)

     N     a    O     R                   (      K                   )

    H   B   r ,    p   e   r     o    x

           i      d   e   s                   (         C                   )

NBS (O)

vicinal

dihaloalk anes

halohydrins

1)OsO4 (D), 2) NaHSO3 vicinal

diols

epoxides

silyl

ethers

carboxylic

acids

vicinal

aminoalcohols

geminal

dihaloalk anes

vicinal

tetraha

loa

lk an

es

aldehydes / k etones

alk enes

alk yl

azidesaminesnitriles   thioethersthiols

HI

ROH / acid (J)

1) Cl2, H2O, 2) NaOH, H2O

   1   )      L           i     A           l    H   4

      2   )    H      2    O

          t   -   B    u    M   e   3       S           i     C           l           /    p     y   r           i      d           i    n   e

m-CBPA

alk anes

     C     R                (          E                )

     N     a     C

alk ynes

1)O3, 2) (CH3)2S

haloak anes

ethers

     N    H   3

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ROADMAP FOR REACTIONS

C a r b o n - c a r b o n  b o nd  f o r m i ng 

r ea c t i o ns  a r e  i nd i c a t e d  b  y 

r ea g e n t s  w r i tt e n  w i t h  s o li d 

b a c k g r o unds  a nd  w h i t e  l e tt e r i ng .

Chapter 15

cyclopropanes

geminal dihalocyclopropanes

alk enes

haloalk anes   alcohols

CHX3

(CH3)3COK 

1)Mg, 2) , 3)H3O+ / H2O

CH2I2

Zn (Cu)

R2CuLi

O

(A)

(B)

(C)

(D)

(E)

(F)

(G)

(H)

( I )

(J)

(K)

 

(L)

(M)

(N)

(O)

Regiochemistry: Markovnikov addition to a  bond

Stereochemistry: anti-addition

Regiochemistry: non-Markovnikov addition to a  bond

Stereochemistry: syn-addition

Works well for methyl and 1° haloalkanes

Stereochemistry: gives c i s -alkenes as products

Stereochemistry: gives t r a ns -alkenes as products

Reactivity of C–H bonds follows 3° > 2° > 1°

Works for methyl, 1°, and 2° haloalkanes

Works for 2° and 3° haloalkanes, may see rearrangements

Works for all haloalkanes except methyl, although a bulky

(non-nucleophilic) base must be used for 1° haloalkanes.

Regiochemistry: follows Zaitzev’s rules so the more substituted

alkene predominates. Stereochemistry: requirement for the

X and H to be eliminated with anti-periplanar geometry.

PBr3 and SOX2 works for methyl, 1°, and 2° haloalkanes.

HX can give rearrangements.

For 1° alcohols

For 2° alcohols

Regiochemistry: the product with the more substituted alkene

predominates

vinyl halides

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ROADMAP FOR REACTIONS

Key:

Chapter 15

Carbon-carbon bond forming 

reactions are indicated by 

reagents written with solid 

backgrounds and white lettering.

Chapter 16

Chapters 15 16

   H   3   O   +   /   H   2   O

   B  r   2 ,  a  c   i   d

H3O+ /H2O

   R   O   H   /   H   +

ROH/H+

cyclopropanes

geminal dihalocyclopropanes

acetals

aldehydes/ ketones

alkenes

haloalkanes alcohols

CHX3

(CH3)3COK

1) Mg, 2) , 3) H3O+ /H2O

CH2I2

Zn (Cu)

1) RC2) H3O+ /H2O

CNa

O

   1   )   R   M  g   X ,   2   )   H   3   O   +

   P   h   3   P   +

   C   R   2  –

   1   )   R   L   i ,   2   )   H   3   O   +

   1   )   N  a   B   H   2 ,   2   )   H   3   O   +

N2H4 , KOH

  a  m   i  n  e ,   N

  a   B   H   3   C   N

   R   2   N   H

   R   N   H   2

Zn (Hg), HCl

   P   t ,   H   2

hemiacetals

 ,-unsaturatedesters

  -haloketones   -hydroxyalkynes cyanohydrins

alkanes

imines

enamines

amines

1) NaCN2) H2O(MeO)2P

1)

2) Base

CH2C

O

OEt

O

R2CuLivinyl halides

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ROADMAP FOR REACTIONS

Key:

Chapter 15

Carbon-carbon bond forming 

reactions are indicated by 

reagents written with solid 

backgrounds and white lettering.

Chapter 16

Chapter 17

Chapters 15 16 17

   H   3   O   +   /   H   2   O

   B  r   2 ,  a  c   i   d

H3O+ /H2O

   S   O   C   l   2

CH2N2

1) LiAlH4 , 2) H3O+ /H2O

ROH acid

   R   O   H   /   H   +

ROH/H+

cyclopropanes

geminal dihalocyclopropanes

acetals

aldehydes/ ketones

alkenes

carboxylicacids

esters

haloalkanes

acid chlorides

alcohols

CHX3

(CH3)3COK

1) Mg, 2) , 3) H3O+ /H

2O

CH2I2

Zn (Cu)

1) RC2) H3O+ /H2O

CNa

1) Mg

2) CO2

3) H3O+ /H2O

R2CuLi

O

   1   )   R   M  g   X ,

   2   )   H   3   O   +

   P   h   3   P   +

   C   R   2  –

   1   )   R   L   i ,   2   )   H   3   O   +

   1   )   N  a   B   H   2 ,

   2   )   H   3   O   +

N2H4 , KOH

  a  m   i  n  e ,   N

  a   B   H   3   C   N

   R   2   N   H

   R   N   H   2

Zn (Hg), HCl

   P   t ,   H   2

hemiacetals

 ,-unsaturatedesters

  -haloketones   -hydroxyalkynes cyanohydrins

alkanes

imines

enamines

amines

1) NaCN2) H2O(MeO)2P

1)

2) Base

CH2C

O

OEt

O

vinyl halides

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ROADMAP FOR REACTIONS

Key:

Chapter 15

Carbon-carbon bond forming 

reactions are indicated by 

reagents written with solid 

backgrounds and white lettering.

Chapter 16

Chapter 17

Chapter 18

Chapters 15 16 17 18

   H   3   O   +   /   H   2   O

   B  r   2 ,  a  c   i   d

H3O+ /H2O

   S   O   C   l   2

CH2N2

1) LiAlH4 , 2) H3O+ /H2O

1) LiAlH4 , 2) H3O+ /H2O

1) LiAlH4 , 2) H3O+ /H2O

   1   )   L   i   A   l   H   4 ,   2   )   H   3   O   +   /   H   2   O

   1   )   D   I   B   A   L ,   2   )   H   3   O   +

H2O acid or base

H2O acid or base

H2O acid or base

ROH acid

RCO2H

   H   2   O

H2O ROH

ROH

   R   O   H   /   H   +

ROH/H+

cyclopropanes

geminal dihalocyclopropanes

acetals

aldehydes/ ketones

alkenes

carboxylicacids

esters

haloalkanes

acid chloridesNHR2

NHR2

   N   H   R   2

acidanhydrides

nitriles

amides

alcohols

CHX3

(CH3)3COK

1) Mg, 2) , 3) H3O+ /H

2O

CH2I2

Zn (Cu)

1) RC2) H3O+ /H2O

CNa

1) Mg

2) CO2

3) H3O+ /H2O

R2CuLi

O

   1   )   R   M  g   X ,   2   )   H   3   O   +

   1   )   R   2   C  u   L   i ,   2   )   H   2   O

   1   )   2   R   M  g   X ,   2   )   H   2   O

   P   h   3   P   +

   C   R   2  –

   1   )   R   L   i ,   2   )   H   3   O   +

   1   )   N  a   B   H   2 ,   2   )   H   3   O   +

N2H4 , KOH

  a  m   i  n  e ,   N

  a   B   H   3   C   N

   R   2   N   H

   R   N   H   2

Zn (Hg), HCl

   P   t ,   H   2

hemiacetals

 ,-unsaturatedesters

  -haloketones   -hydroxyalkynes cyanohydrins

alkanes

imines

enamines

amines

1) NaCN2) H2O(MeO)2P

1)

2) Base

CH2C

O

OEt

O

vinyl halides

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Carbon-carbon bond forming 

reactions are indicated by 

reagents written with solid 

backgrounds and white lettering.

ROADMAP FOR REACTIONS

H3O+R3

R2

R1O

R4HONaOR/HOR

 Aldol Reaction

various enolatesor amines

 Michael Reaction

1) R2CuLi2) H3O+ /H2O

1) 2°-amine2) acid chloride3) H3O+ /H2O

1) NaOEt/HOEt2) H3O+ /H2O

1) LDA2) R-X3) H3O+ /H2O

1) 2°-amine2) R-X

3) H3O+ /H2O

ketones,aldehydes

-Hydroxy carbonyls

ClaisenCondensation

esters

-ketoesters

1) NaOEt/HOEt2) H3O+ /H2O

R4   R5

R3

R1

R6

R7

R8R2

OO

O

DieckmannCondensation

diesters

cyclic -ketoesters

1) NaOEt/HOEt2) R-X3) NaOH, H2O4) H3O+ /H2O5)  

1) NaOEt/HOEt2) R-X3) NaOH, H2O4) H3O+ /H2O5)  

 Malonic Ester Synthesis

malonicesters

alkylated carboxylic acids

 Acetoacetic Ester Sythesis

acetoaceticesters

alylated methyl ketones

R3R2

R1

O

R4

O

OH

OH

R1

O

R1

R2

O

H3C

H3C

R1

O

R1

R2

Alkylated -carbons

R3

R2

R1

O

R4

,-Unsaturated carbonyls

-Alkylated carbonyls

R2

R3

R4

R1

O

Nu

Nu = enolate formingspecies or amines

R2

R3

R4

R1   R5

O

Chapter 19

R2   R3

R1   R4

O O

R2   R3

OR4R1

O O

-Dicarbonyls

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ROADMAP FOR REACTIONS

Carbon-carbon bond forming 

reactions are indicated by reagents 

written with solid backgrounds 

and white lettering.

HX

alkene

dienes

cyclohexenes

allylic halides

Chapter 20

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ROADMAP FOR REACTIONS

H2CrO4

H2CrO4NBS

carboxyphenols

quinones

aryl carboxylicacids

benzylicbromides

Chapter 20

Key:Carbon-carbon bond forming 

reactions are indicated by reagents 

written with solid backgrounds 

and white lettering.

Chapter 21

HX

alkene

dienes

cyclohexenes

allylic halides

Chapters 20 21

alkylbenzenes

phenols1) NaOH2) CO2

3) H3O+ /H2O

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ROADMAP FOR REACTIONS

H2CrO4

H2CrO4NBS

   N  a   O   H ,   H   2   O

   H   2 ,   N   i

HNO3 , H2SO4

 H2SO4 , SO3

   1

   )   F  e ,   H   C   l

   2

   )   N  a   O   H

phenols

carboxy

phenols

quinones

anilines

nitrobenzenes

aryl carboxylicacids

benzylicbromides

1) NaOH2) CO2

3) H3O+ /H2O

Chapter 20

Key:Carbon-carbon bond forming 

reactions are indicated by reagents 

written with solid backgrounds 

and white lettering.

Chapter 21

Chapter 22

sulfobenzenes

acyl benzenes

aryl rings

HX

alkene

R(CO)X, AlX3

dienes

cyclohexenes

allylic halides

Chapters 20 21 22

   R   X ,   A   l

   X   3

   3   °  -   R   O   H ,   H

   3   P   O   4

H3PO4

NaNH2 , NH3

X2 , FeX3

alkylbenzenes

halobenzenes

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ROADMAP FOR REACTIONS

H2O

H2CrO4

H2CrO4NBS

   N  a   O   H ,   H   2   O

   H   2 ,   N   i

HNO3 , H2SO4

 H2SO4 , SO3

   1   )   F  e ,   H   C   l

   2   )   N  a   O   H

phenols

carboxyphenols

quinones

   H   3   P   O   2

1) HNO2 , 2) HClanilines

nitrobenzenes

alkylbenzenes

aryl carboxylicacids

benzylicbromides

halobenzenes

1) KN3 ,2) H2O,3) LiAlH4 ,4) H3O+ /H2O

1) NaOH2) CO2

3) H3O+ /H2O

   1   )  e  x  c  e  s  s   M  e   l

   2   )   N  a   O   H ,   h  e  a   t

   1   )   H   2   O   2 ,   2   )   h  e  a   t

Chapter 20Key:

Carbon-carbon bond forming 

reactions are indicated by reagents 

written with solid backgrounds 

and white lettering.

Chapter 21

Chapter 22

Chapter 23

epoxides

   H   B   F   4

vicinal aminoalcohols

aryl fluorides

aryl nitriles

sulfobenzenes

acyl benzenes

KIaryl iodides

aryl rings

ketones

HX

alkene

KCN, CaCN

R(CO)X, AlX3

dienes

aryldiazonium

salts

cyclohexenes

amines

alkenes

allylic halides

Chapters 20 21 22 23

   R   X ,   A   l   X   3

   3   °  -   R   O   H ,   H   3   P   O   4

H3PO4

HNO2

NaNH2 , NH3

X2 , FeX3