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ALDEHYDES AND KETONES I. CHAPTER 16. CHEMISTRY OF THE C=O GROUP. Sections 16.1 and 16.2 Nomenclature of Aldehydes and Ketones. Learn on your own. Sections 16.3-16.5 Review and Overview. Read on your own. Section 16.6 Cyanide addition. Lecture. Section 16.7

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Presentation Transcript
slide2

CHAPTER 16

CHEMISTRY OF THE C=O GROUP

Sections 16.1 and 16.2

Nomenclature of Aldehydes and Ketones

Learn on

your own.

Sections 16.3-16.5

Review and Overview

Read on your own

Section 16.6

Cyanide addition

Lecture

Section 16.7

Addition of Organometallics

Totally review

Section 16.8

Read on your own

Bisulfite Addtion

Sections 16.9-16.11

Lecture

Jump to Sections 16.15-16.19

Lecture

Go Back to Sections 16.12-16-14

Lecture

slide3

STRUCTURE

Aldehyde

Ketone

slide5

IUPAC Nomenclature of Ketones

  • Choose the longest continuous carbon chain that contains the carbonyl carbon
  • Number from the end of the chain closest to the carbonyl carbon
  • Ketone ending is -one

Do the ketonessection of Organic Nomenclature

program!

slide6

EXAMPLES

2-Pentanone

4-Ethyl-3-hexanone

slide7

3-Isopropylcyclopentanone

or 3-(1-Methylethyl)cyclopentanone

common or trivial names

KETONES

Common, or Trivial, Names
  • Name each group attached to the carbonyl group as an alkyl group
  • Combine into a name, according to the pattern:

alkyl alkyl’ ketone

NOTE: This is not all one word!

slide9

Example of Common Names

Methyl propyl ketone

Diethyl ketone

slide10

SPECIAL CASES

diphenyl ketone

dimethyl ketone

benzophenone

acetone

A common laboratory

solvent and cleaning

agent

methyl phenyl ketone

KNOW

THESE

acetophenone

slide11

IUPAC Nomenclature of Aldehydes

  • Choose the longest continuous carbon chain that contains the carbonyl carbon
  • Number from the end of the chain closest to the carbonyl carbon (carbon #1!)
  • Aldehyde ending is -al

Do the aldehydessection of Organic Nomenclature

program.

slide12

EXAMPLES

aldehyde group is

always carbon 1

pentanal

3

1

4

2

2-chloro-3-methylbutanal

slide13

RECOGNIZE

THESE

Common Names of the Aldehydes

slide14

SPECIAL CASES

formaldehyde

benzaldehyde

KNOW

THESE

acetaldehyde

slide15

Forming Common Names of Aldehydes

USE OF GREEK LETTERS

…….

w is always the end of the chain, no matter how long

a-chlorocaproaldehyde

w-chlorocaproaldehyde

( a-chlorohexanal )

( w-chlorohexanal )

slide16

REACTIVITY OF THE C=O GROUP

NUCLEOPHILIC ADDITION

slide17

..

..

-

d-

:

:

:

d+

+

GENERALIZED CHEMISTRY

THE CARBONYL GROUP

nucleophilic

at oxygen

H+ or E+

electrophiles

add here

nucleophiles

attack here

Nu:

electrophilic

at carbon

slide19

THE CARBONYL GROUP IS PLANAR

(SP2 HYBRIDIZED)

Nu:

.

.

..

C

O

..

Nu:

nucleophiles can attack from either top or bottom

slide20

LUMO OF FORMALDEHYDE

s*CH

s*CO

p*

(LUMO)

nO

H

H

p

sCO

sCH

..

Nu:

nucleophiles add

to the larger lobe

(on carbon)

:

slide21

NUCLEOPHILIC ADDITION TO C=O

MECHANISMS

IN ACID AND IN BASE

slide22

Nucleophilic Addition to Carbonyl

Basic or Neutral Solution

an

alkoxide

ion

-

or on adding acid

Good nucleophiles

and strong bases

(usually charged)

BASIC SOLUTION

slide23

Nucleophilic Addition to Carbonyl

Acid Catalyzed

more reactive to

addition than the un-

protonated precursor

(+)

Acid catalysis speeds the rate of

addition of

weak nucleophiles and

weak bases (usually uncharged).

ACIDIC SOLUTION

stronger acid

protonates the

nucleophile

pH 5-6

slide25

Addition of Cyanide

:C N:

Buffered to pH 6-8

a cyanohydrin

In acid solution there would be little CN-,

and HCN (g) would be a problem (poison).

A cyanohydrin

slide26

CYANIDE ION BONDS TO HEMOGLOBIN

..

Cyanide bonds

(irreversibly) to the

site (Fe II) where

oxygen usually bonds.

CYANIDE IS

IS A POISON

..

You die of

suffocation -

lack of oxygen.

HCN is a gas that you can easily breathe into your lungs.

slide27

SYNTHESIS OF

a-HYDROXYACIDS

slide28

SYNTHESIS OF AN a-HYDROXYACID

NaCN

a cyanohydrin

pH 8

acetophenone

1) NaOH/H2O/D

2) H3O+

Aldehydes also work unless

they are benzaldehydes,

which give a different reaction

(benzoin condensation).

slide29

HYDROLYSIS OF THE

NITRILE GROUP

slide30

SYNTHESIS OF NITRILES (AND CYANOHYDRINS)

REVIEW

C=O + NaCN C-OH

CN

cyanohydrin

acetone

R-X + NaCN R-CN + NaX

SN2

nitrile

….. both can be hydrolyzed

slide31

NaOH

+

H2O/D

synthesis of

carboxylic acids

HYDROLYSIS OF THE CYANO GROUP (NITRILES)

METHOD ONE : strong base + H2O + heat

gas

..

:

..

-

+

:

..

H3O+

neutralize

OVER ALL

..

:

R-CN

..

..

R-COOH

Nitriles are hydrolyzed to carboxylic acids.

slide32

synthesis of

carboxylic acids

HYDROLYSIS OF THE CYANO GROUP (NITRILES)

METHOD TWO : strong acid + H2O + heat

..

:

H2SO4

+

..

H2O/D

..

OVER ALL

no mechanism

at this time

R-CN

R-COOH

Nitriles are hydrolyzed to carboxylic acids.

slide33

ORGANOMETALLICS

REVIEW FROM CHAPTER 15

slide34

These reagents cannot

exist in acid solution

Synthesis of Alcohols

Addition of Organometallic Reagents

ether

(R-Li)

:R -

workup

step

alcohol

summary of reactions of organometallics with carbonyl compounds
Summary of Reactions of Organometallics with Carbonyl Compounds
  • Organometallics with ketones yield

tertiary alcohols

  • Organometallics with aldehydes yield

secondary alcohols

  • Organometallics with formaldehyde yield

primary alcohols.

  • Organometallics with carbon dioxide yield

carboxylic acids.

All review

to you

etc.