Aldehydes and Ketones
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Aldehydes and Ketones. Before you can learn about aldehydes and ketones, you must first know something about the nomenclature of carboxylic acids since many of the names of aldehydes and ketones are derived from the names of the corresponding carboxylic acids. Carboxylic acids:

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Before you can learn about aldehydes and ketones, you must first know something about the nomenclature of carboxylic acids since many of the names of aldehydes and ketones are derived from the names of the corresponding carboxylic acids.


Carboxylic acids: first know something about the nomenclature of carboxylic acids since many of the names of aldehydes and ketones are derived from the names of the corresponding carboxylic acids.

R-COOH, R-CO2H,

Common names:

HCO2H formic acid L. formica ant

CH3CO2H acetic acid L. acetum vinegar

CH3CH2CO2H propionic acid G. “first salt”

CH3CH2CH2CO2H butyric acid L. butyrum butter

CH3CH2CH2CH2CO2H valeric acid L. valerans


Carboxylic acids, common names first know something about the nomenclature of carboxylic acids since many of the names of aldehydes and ketones are derived from the names of the corresponding carboxylic acids.:

CH3(CH2)4CO2H caproic acid L. caper goat

CH3(CH2)5CO2H ---

CH3(CH2)6CO2H caprylic acid

CH3(CH2)7CO2H ---

CH3(CH2)8CO2H capric acid

CH3(CH2)9CO2H ---

CH3(CH2)10CO2H lauric acid oil of lauryl


5 4 3 2 1 first know something about the nomenclature of carboxylic acids since many of the names of aldehydes and ketones are derived from the names of the corresponding carboxylic acids.

C—C—C—C—C=O

δ γ β α used in common names


Special names! first know something about the nomenclature of carboxylic acids since many of the names of aldehydes and ketones are derived from the names of the corresponding carboxylic acids.


ALDEHYDES AND KETONES first know something about the nomenclature of carboxylic acids since many of the names of aldehydes and ketones are derived from the names of the corresponding carboxylic acids.

“carbonyl” functional group:

Aldehydes Ketones


Nomenclature: first know something about the nomenclature of carboxylic acids since many of the names of aldehydes and ketones are derived from the names of the corresponding carboxylic acids.

Aldehydes, common names:

Derived from the common names of carboxylic acids;

drop –ic acid suffix and add –aldehyde.

CH3

CH3CH2CH2CH=O CH3CHCH=O

butyraldehyde isobutyraldehyde

(α-methylpropionaldehyde)


Aldehydes, first know something about the nomenclature of carboxylic acids since many of the names of aldehydes and ketones are derived from the names of the corresponding carboxylic acids.IUPAC nomenclature:

Parent chain = longest continuous carbon chain containing the carbonyl group; alkane, drop –e, add –al. (note: no locant, -CH=O is carbon #1.)

CH3

CH3CH2CH2CH=O CH3CHCH=O

butanal 2-methylpropanal

H2C=O CH3CH=O

methanal ethanal


Ketones, first know something about the nomenclature of carboxylic acids since many of the names of aldehydes and ketones are derived from the names of the corresponding carboxylic acids.common names:

Special name:acetone

“alkyl alkyl ketone” or “dialkyl ketone”


(o)phenones first know something about the nomenclature of carboxylic acids since many of the names of aldehydes and ketones are derived from the names of the corresponding carboxylic acids.:

Derived from common name of carboxylic acid, drop –ic acid, add –(o)phenone.


Ketones: first know something about the nomenclature of carboxylic acids since many of the names of aldehydes and ketones are derived from the names of the corresponding carboxylic acids.IUPAC nomenclature:

Parent = longest continuous carbon chain containing the carbonyl group. Alkane, drop –e, add –one. Prefix a locant for the position of the carbonyl using the principle of lower number.


Physical properties: first know something about the nomenclature of carboxylic acids since many of the names of aldehydes and ketones are derived from the names of the corresponding carboxylic acids.

polar, no hydrogen bonding

mp/bp are relatively moderate for covalent substances

water insoluble

(except: four-carbons or less)


Spectroscopy: first know something about the nomenclature of carboxylic acids since many of the names of aldehydes and ketones are derived from the names of the corresponding carboxylic acids.

IR: C=O stretch, strong ~1700 cm-1

RCHO 1725 ArCHO 1700

R2CO 1710 ArCOR 1690

C—H stretch for aldehydes 2720

nmr: -CHO 9-10 ppm


acetophenone first know something about the nomenclature of carboxylic acids since many of the names of aldehydes and ketones are derived from the names of the corresponding carboxylic acids.

C=O

stretch


valeraldehyde first know something about the nomenclature of carboxylic acids since many of the names of aldehydes and ketones are derived from the names of the corresponding carboxylic acids.

CHO

C—H

stretch

2720 cm-1

C=O stretch


valeraldehyde first know something about the nomenclature of carboxylic acids since many of the names of aldehydes and ketones are derived from the names of the corresponding carboxylic acids.

CH3CH2CH2CH2CH=O

a b c d e

-CHO


Oxidation/Reduction: first know something about the nomenclature of carboxylic acids since many of the names of aldehydes and ketones are derived from the names of the corresponding carboxylic acids.

oxidation numbers:

oxidation

-4 -2 0 +2 +4

CH4 CH3OH H2C=O HCO2H CO2

alkane alcohol aldehyde carboxylic acid

reduction


  • Aldehydes, syntheses: first know something about the nomenclature of carboxylic acids since many of the names of aldehydes and ketones are derived from the names of the corresponding carboxylic acids.

  • Oxidation of 1o alcohols

  • Oxidation of methylaromatics

  • Reduction of acid chlorides

  • Ketones, syntheses:

  • Oxidation of 2o alcohols

  • Friedel-Crafts acylation

  • Coupling of R2CuLi with acid chloride


Aldehydes synthesis 1) oxidation of first know something about the nomenclature of carboxylic acids since many of the names of aldehydes and ketones are derived from the names of the corresponding carboxylic acids.primary alcohols:

RCH2-OH + K2Cr2O7, special conditions  RCH=O

RCH2-OH + C5H5NHCrO3Cl  RCH=O

(pyridinium chlorochromate)

[With other oxidizing agents, primary alcohols  RCOOH]


Aldehyde synthesis: 2) oxidation of methylaromatics: first know something about the nomenclature of carboxylic acids since many of the names of aldehydes and ketones are derived from the names of the corresponding carboxylic acids.

Aromatic aldehydes only!


Aldehyde synthesis: 3) reduction of acid chloride first know something about the nomenclature of carboxylic acids since many of the names of aldehydes and ketones are derived from the names of the corresponding carboxylic acids.


Ketone synthesis: 1) oxidation of first know something about the nomenclature of carboxylic acids since many of the names of aldehydes and ketones are derived from the names of the corresponding carboxylic acids.secondary alcohols


Ketone synthesis: 2) Friedel-Crafts acylation first know something about the nomenclature of carboxylic acids since many of the names of aldehydes and ketones are derived from the names of the corresponding carboxylic acids.

Aromatic ketones (phenones) only!


Friedel Crafts acylation does not work on deactivated rings. first know something about the nomenclature of carboxylic acids since many of the names of aldehydes and ketones are derived from the names of the corresponding carboxylic acids.


Ketone synthesis: 3) coupling of RCOCl and R first know something about the nomenclature of carboxylic acids since many of the names of aldehydes and ketones are derived from the names of the corresponding carboxylic acids.2CuLi


  • Aldehydes, syntheses first know something about the nomenclature of carboxylic acids since many of the names of aldehydes and ketones are derived from the names of the corresponding carboxylic acids.:

  • Oxidation of 1o alcohols

  • Oxidation of methylaromatics aromatic only

  • Reduction of acid chlorides

  • Ketones, syntheses:

  • Oxidation of 2o alcohols

  • Friedel-Crafts acylation aromatic only

  • Coupling of R2CuLi with acid chloride


K first know something about the nomenclature of carboxylic acids since many of the names of aldehydes and ketones are derived from the names of the corresponding carboxylic acids.2Cr2O7, special cond.

or C5H5NHCrO3Cl

1o alcohol

Ar-CH3

CrO3 H2O

(AcO)2O

aldehyde

acid chloride

LiAlH(O-t-Bu)3


2 first know something about the nomenclature of carboxylic acids since many of the names of aldehydes and ketones are derived from the names of the corresponding carboxylic acids.o alcohol

NaOCl, etc.

ketone

acid chloride + ArH

AlCl3

acid chloride + R2CuLi


  • outline three different syntheses for benzaldehyde first know something about the nomenclature of carboxylic acids since many of the names of aldehydes and ketones are derived from the names of the corresponding carboxylic acids.

  • outline three different syntheses for benzophenone

  • outline a different synthesis for each of the following compounds:

  • cyclohexanone, 4-bromobenzaldehyde, 2-pentanone, valeraldehyde, acetophenone, isobutyraldehyde,


Synthesize benzaldehyde three different ways. first know something about the nomenclature of carboxylic acids since many of the names of aldehydes and ketones are derived from the names of the corresponding carboxylic acids.


Synthesize benzophenone three different ways. first know something about the nomenclature of carboxylic acids since many of the names of aldehydes and ketones are derived from the names of the corresponding carboxylic acids.


cyclohexanone, 4-bromobenzaldehyde, 2-pentanone, valeraldehyde, acetophenone, isobutyraldehyde, using a different method for each one.


The methods could be reversed for the last two syntheses. valeraldehyde, acetophenone, isobutyraldehyde, using a different method for each one.


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