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    1 Roh Carboxylic Acids: H Cro

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    andrewwroble
    The document provides an overview of common organic reactions involving aromatic compounds (arenes). It outlines methods for halogenating, nitrating, and sulfonating arenes. It also describes processes for alkylating arenes using Friedel-Crafts reactions and synthesizing arylethers, benzoic acids, benzyl halides, and benzyl bromides from arenes. The final section discusses hydrogenation reactions of arenes catalyzed by platinum or palladium, which can form either the desired saturated product or unwanted side products.

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    © All Rights Reserved
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    1 Roh Carboxylic Acids: H Cro

    Uploaded by

    andrewwroble
    72 views15 pages
    The document provides an overview of common organic reactions involving aromatic compounds (arenes). It outlines methods for halogenating, nitrating, and sulfonating arenes. It also describes processes for alkylating arenes using Friedel-Crafts reactions and synthesizing arylethers, benzoic acids, benzyl halides, and benzyl bromides from arenes. The final section discusses hydrogenation reactions of arenes catalyzed by platinum or palladium, which can form either the desired saturated product or unwanted side products.

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    The document provides an overview of common organic reactions involving aromatic compounds (arenes). It outlines methods for halogenating, nitrating, and sulfonating arenes. It also describes processes for alkylating arenes using Friedel-Crafts reactions and synthesizing arylethers, benzoic acids, benzyl halides, and benzyl bromides from arenes. The final section discusses hydrogenation reactions of arenes catalyzed by platinum or palladium, which can form either the desired saturated product or unwanted side products.

    Copyright:

    © All Rights Reserved
    Download as PDF, TXT or read online from Scribd
    Download as pdf or txt
    72 views15 pages

    1 Roh Carboxylic Acids: H Cro

    Uploaded by

    andrewwroble
    The document provides an overview of common organic reactions involving aromatic compounds (arenes). It outlines methods for halogenating, nitrating, and sulfonating arenes. It also describes processes for alkylating arenes using Friedel-Crafts reactions and synthesizing arylethers, benzoic acids, benzyl halides, and benzyl bromides from arenes. The final section discusses hydrogenation reactions of arenes catalyzed by platinum or palladium, which can form either the desired saturated product or unwanted side products.

    Copyright:

    © All Rights Reserved
    Download as PDF, TXT or read online from Scribd
    Download as pdf or txt
    of 15
    At a glance
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    The document discusses organic chemistry reactions including substitution, elimination, oxidation, reduction, etc of various functional groups like alcohols, carboxylic acids, aromatics.

    Alcohols can undergo oxidation to form aldehydes and ketones, they can be dehydrated to form alkenes, and they can form esters and ethers via nucleophilic substitution reactions.

    Carboxylic acids can form acid derivatives like acid chlorides, anhydrides, esters and amides. They also undergo reactions like esterification and transesterification.

    O

    H2CrO4
    R

    OH

    or Na2Cr2O7 /H2SO4
    or CrO3/H2SO4

    1o ROH

    OH

    Carboxylic Acids

    OH

    H2CrO4
    R'

    or Na2Cr2O7 /H2SO4
    or CrO3/H2SO4

    2o ROH

    R
    R'
    Ketones

    PCC or PDC
    R

    OH

    CH2Cl2

    1 ROH

    Aldehydes

    OH

    O
    PCC or PDC

    R'

    CH2Cl2

    2 ROH

    R
    R'
    Ketones

    Nao or Ko
    R

    OH
    ROH (solvent)

    2R

    O Na

    NaH
    OH

    2R
    ether; THF or alkanes

    O Na + H2

    (reaction is irreversible)

    OH

    HX
    R''

    R'

    R'

    3o ROH

    3 Halides

    OH

    HX (conc)
    R

    R''

    R (H)

    Heat

    R (H)
    H

    1o & 2o Halides

    1o & 2o ROH

    OH

    Cl
    SOCl2

    R (H)

    Pyridine or N(Et)3

    R (H)

    1o & 2o ROH

    1o & 2o Chloride

    OH

    R (H)
    H3O+

    R
    CH2

    R (H)
    R (H)

    R
    CH

    -H2O

    Alkene
    (Zaitsev's rule)

    ROH
    OH

    OR'

    1) Nao
    R

    R (H)
    R (H)
    ROH

    R (H)

    2) R'X
    o

    R
    o

    1 or 2

    R (H)
    R (H)
    Ether

    OH + H

    H2SO4
    OR'

    R
    C

    CH2 + H

    H2SO4
    OR'

    OR'

    Heat

    OR'
    C

    Heat

    CH2H

    2 H2C

    CH2

    O2
    2 H2C

    Ag

    R
    C

    CH2

    CH2

    RCO3H
    C

    CH2Cl2

    CH2

    R
    R

    OH

    NaOH
    C

    CH2

    C
    R

    O
    C
    R
    R

    CH2

    CH2

    OH

    H3O+

    C
    R
    R

    CH2
    OH

    O
    C

    CH2

    OH

    Na+CNH2O

    (H)R

    CH2
    CN

    (H)R

    O
    C

    CH2

    2) H2O

    (H)R

    OH

    1) Na+ C CH

    (H)R

    O
    C

    CH2
    CH

    OH
    NH3

    CH2

    (H)R

    CH2
    NH2

    (H)R

    Second Semester
    Chap 15:
    Mg
    R

    Mg

    ether or THF

    MgBr

    Mg
    ether or THF

    OH

    O
    1) R"
    R

    (H)R

    CH2

    2) H3O+

    Mg

    X
    R

    (H)R

    CH2
    R"

    OH
    1) R"

    Mg

    C
    R

    2) H3O+

    R(H)

    R(H)
    R"

    R'

    R2CuLi

    R'

    ether or THF

    R
    +

    R2CuLi

    ether or THF

    Cl3CH + K+ -OtBu

    Cl2C
    used immediately

    R
    Cl2C

    H
    Cl

    +
    R

    Cl
    Stereospecific Rxn

    O
    H2CrO4 (aq)

    C
    R

    aldehyde

    or Na2Cr2O7 /H2SO4
    or CrO3/H2SO4

    C
    R

    Carboxylic Acid

    O
    2

    O
    O2

    C
    R

    OH

    aldehyde

    C
    R

    OH

    Carboxylic Acid

    OH
    1) LiAlH4

    H(R)

    2) H2O

    H
    H(R)

    Carbonyl

    Alcohol
    O

    OH
    NaBH4

    C
    R

    H(R)

    MeOH; H2O

    C
    R

    Carbonyl

    H
    H(R)

    Alcohol
    O

    OH
    H2

    C
    R

    H(R)

    RT, 2 atm

    H
    H(R)

    Carbonyl

    Alcohol

    O
    H2C

    2 H2

    H2
    C

    C
    C
    H

    Ni

    H(R)

    H
    C

    H
    H
    H(R)

    Carbonyl

    Alcohol

    C
    R

    C
    H(R)

    Zn(Hg), HCl

    Carbonyl

    H
    H(R)

    Hydrocarbon
    O
    C
    R

    N2H4; KOH
    heat;
    H(R)

    Carbonyl

    HO

    C
    OH

    H
    H(R)

    Hydrocarbon

    Nucleophilic Acyl Substitution

    O
    R'OH

    C
    R

    OH

    (cat)

    OR'

    Carboxylic Acid

    Ester

    O
    HOH

    C
    R

    + HCl

    Cl

    Acid Chloride

    OH

    Carboxylic Acid

    + HOH

    H2O

    H+ (cat)

    C
    OH

    Carboxylic Acid

    Acid Anhydride

    H2O
    O

    H+ (cat)
    O

    C
    R

    OR'
    C

    Ester

    NaOH

    Carboxylic Acid

    O
    Na
    C
    R

    OH

    H3O

    R'OH

    H2O
    O

    H+ (cat)
    O

    C
    R

    NH2
    C

    Amide

    NaOH

    OH

    NH4

    Carboxylic Acid

    O
    H3O+

    Na
    C
    R

    H2O
    O

    H+ (cat)
    O

    C
    R

    NH2
    C

    Amide

    NaOH

    NH4

    OH

    Carboxylic Acid

    O
    +

    Na

    H3O

    C
    R

    O
    R'OH

    C
    R

    Cl

    Acid Chloride

    + HCl

    C
    OR'
    Ester

    R'OH
    R

    O
    Acid Anhydride

    C
    R

    C
    OR'

    Ester

    HO

    Carboxylic Acid

    O
    R''OH

    OR'
    Ester

    R'OH

    OR''
    Ester

    Alcohol

    O
    Cl

    2 R'NH2

    C
    R

    Cl

    Acid Chloride

    R'NH3

    NHR'

    Ammonium
    Hydrochloride Salt

    Amide

    O
    2 R'NH2

    R'NH3

    Acid Anhydride

    NHR'

    O
    2 R'NH2

    C
    R

    OR''

    Ester

    NHR'

    R"OH
    Alcohol

    Amide

    Na
    C
    R

    +
    Cl

    Acid Chloride

    C
    O

    C
    R

    Sodium
    Carboxylate Salt

    Ammonium
    Carboxylate Salt

    Amide

    C
    O

    Acid Anhydride

    OH
    1) 2 eq R'MgBr

    C
    R

    OR'

    R'

    2) H3O+

    Ester

    R'

    3o Alcohol

    OH
    1) 2 eq R'Li

    C
    R

    OR'

    R'

    2) H3O+

    Ester

    + HOR'

    R'

    3o Alcohol

    O
    1) (R')2CuLi

    C
    R

    + HOR'

    Cl

    2) H3O+

    Acid Chloride

    R'

    Ketones

    OH
    1) LAH

    C
    R

    OR'

    2) H3O+

    C
    R

    Ester

    H
    H

    1o Alcohol

    O
    1) DiBAlH

    C
    R

    OR'

    2) H3O+

    Ester
    2AlH2

    C
    R

    Aldehydes

    O
    H2
    C

    1) LAH
    C
    R

    2) H3O+

    NH2

    NH2
    -N(H)R2

    -N(H)R2
    Amide

    Amines

    H2
    C

    1) LAH
    R

    2) H3O+

    NH2

    Nitrile
    Amines

    O
    C
    R

    H3O+

    H(R')

    OH

    H3O+

    +
    HC
    O

    C
    R

    OH-

    H(R')

    H(R')

    Na+-OR

    C
    OR

    C
    H3C

    OR

    ROH

    OH

    -hydroxycarbonyl

    H3C

    H(R')

    -unsaturated carbonyl

    C
    C
    H2
    -ketoester

    + ROH
    OR

    1) Na+-OR / ROH

    C
    H2

    C
    R

    OR

    2)

    R"

    O
    C
    HC

    OR

    R"

    -ketoester

    O
    N

    N
    H

    Br
    H

    Br

    HCl( aq)

    R
    -substituted ketone

    Enamines

    Iminium Salt

    Chemistry of Acidic Methylene compounds (Acetoacetic & Malonic Ester Synthesis):


    O

    1) Na+-OR / ROH

    C
    H2

    OR

    C
    R

    2)

    R"

    O
    C
    HC

    R"

    -ketoester

    1) NaOH( aq)

    2) H3O+( aq)
    3) heat

    HC
    R"

    OR

    OR

    C
    R

    CH2
    O
    R"
    This is irreversible and leds to
    ketone products

    Conjugate Addition (1,4 addition or Michael Addition):


    1

    Nu

    Nu

    3
    2

    Nu

    OH

    The Robinson Ring Anulation:

    Stage 1:
    Michael Addition

    H2CH
    O

    Stage 2:
    Intramolecular
    Aldol Condensation

    Chapter 22
    X
    X2
    FeX3

    Arenes

    Halogenated arenes

    NO2
    HNO3
    H2SO4

    Arenes

    Nitro arenes
    SO3H
    SO3
    H2SO4

    Arenes

    Arene Sulfonic Acids

    R
    R

    Cl

    AlCl3
    Arenes

    Alkylbenzenes
    O

    O
    C
    R

    Cl
    AlCl3

    Arenes

    Acylbenzenes

    OH
    H2
    C
    R

    Phenol

    O
    Cl

    R
    C
    H2

    NaOH(aq);
    CH2Cl2;
    Bu4N+BrArylethers

    CHR

    C
    OH

    H2CrO4
    or
    KMnO4
    Benzoic Acids

    Arene

    X
    CHR2

    R2C

    X2
    heat or h

    Arene

    Benzyl Halides
    Br
    CHR2

    R2C

    NBS
    peroxides

    Arene

    Benzyl Bromides

    H2
    C

    H2
    O

    Pt or Pd

    HO

    the
    desired
    product

    CH3

    the side product

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