Aldehydes & Ketones

Chapter 19 guide to aldehydes & ketones

Aldehydes

Nomenclature for what?

• parent name is always the carbon carbonyl. It’ll be carbon one as well

• the end of the name will end w/ -al

e.g.,

• hexanal

• 2,3-dimethylbutanal (shown in picture)

Ketones

Nomenclature for what?

• carbon of this group should have lowest number possible

• end of the name will end with -one

e.g.,

• Butanone

• 4-chloro-5-methylhexanone (shown in picture)

Formaldehyde

This aldehyde’s common name is what?

Acetaldehyde

This aldehyde’s common name is what?

Acetophenone

This ketone’s common name is what?

Acetone

This ketone’s common name is what?

Benzophenone

This ketone’s common name is what?

Imine

Different C groups of what?

nitrogen double bonded

primary

An imine is formed by what kind of amines?

Enamine

Different C groups of what?

Nitrogen one away from double bond

secondary

An enamine is formed by what kind of amines?

Acetal

Different C groups of what?

oxygen with 2 C groups coming off

Hemiacetal

Different C groups of what?

one alcohol and one oxygen w/ C group

ketones

All secondary (2°) alcohols will oxidize into what?

ring w/ ketone

What is the resulting product from these?

mixture of methyl ketone

What is the result product from these?

internal bond to _________.

Reagent:

HgSO4

—-—>

H2SO4, H20

methyl ketone

What is the result product from this?

terminal bond to ____________.

Reagent:

HgSO4

—-—>

H2SO4, H2O

aldehyde

What is the result product from this?

terminal end to _____.

Reagent:

1.) 9-BBN

—-—>

2.) H2O2, NaOH

aldehyde substituent

What is the result product from this?

• from primary alcohols

Reagents:

DMP

—-—>

CH2Cl2

PCC

—-—>

CH2Cl2

CH2Cl2

—-—>

DMSO, Et3N

Aldehydes

What is more reactive?

aldehydes or ketones

aliphatic

What is more reactive?

aliphatics (non-aromatic) or aromatics

add OH

Starting product: aldehyde or ketone

Reagents:

LiAl₄

—-—>

H3O+

(LiAl₄ is a strong reducing agent)

add N-NH2

Starting product: aldehyde or ketone

Reagent:

NH₂NH₂, [H+]

add N-OH

Starting product: aldehyde or ketone

Reagent:

NH₂OH, [H+]

move double bond, add N with 2 R groups

Starting product: aldehyde or ketone

Reagent:

R₂NH, [H+]

add N-R

Starting product: aldehyde or ketone

Reagent:

RNH₂, [H+]

Connect 2 S groups by bridgehead

Starting product: aldehyde or ketone

Reagent:

HS/\/SH, [H+]

—-—>

-H2O

two O’s connected with a bridgehead

Starting product: aldehyde or ketone

Reagent:

HO/\/OH, [H+]

—-—>

-H2O

Acetal (OR and OR)

Starting product: aldehyde or ketone

Reagent:

[H+]

—-—>

ROH, -H2O

(R is any carbon/H group)

add 2 OH groups

Starting product: aldehyde or ketone

Reagent:

[H+], H2O

replace a group with O-

Starting product: aldehyde or ketone

Reagent:

RCO₃H

remove the O

Starting product: aldehyde or ketone

Reagent:

H2C=PPh₃

add an OH and a CN

Starting product: aldehyde or ketone

Reagent:

KCN, HCl

or

KCN, H3O+

add an OH and an R group

Starting product: aldehyde or ketone

Reagent:

1.) RMgBr

—-—>

H3O+

(MgBr is a reducing agent)

replace with 2 H’s

Starting product: =N-NH₂

Reagent:

NaOH, H2O

—-—>

heat

replace with 2 H’s

Starting product: 2 S groups connected by a bridgehead

Reagent:

Raney Nickel