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Chapter 15 Aldehydes and Ketones

Milbank High School

Objectives/Study Questions

1.What is the general structure for an aldehyde? A ketone? 2.How are the common names of aldehydes and ketones determined? How are aldehydes and ketones named using IUPAC nomenclature? 3.Why are the boiling points of aldehydes and ketones higher than those of ethers and alkanes of similar molar masses, but lower than those of comparable alcohols?

Objectives/Study Questions

4.How do the solubilities of aldehydes and ketones of four carbons or less compare to the solubilities of comparable alkanes and alcohols in water? 5.How are aldehydes and ketones prepared? 6.What typical reactions take place with aldehydes and ketones? 7.What are some common aldehydes and ketones and their uses?

Carbonyl Group
Carbon atom joined to oxygen by a double bond Ketones Aldehydes

Aldehydes

Comes from alcohol dehydrogenation Obtained by removing of a hydrogen from an alcohol

Aldehydes
Both common and IUPAC names frequently used Common names from acids from which aldehydes can be converted

Aldehydes
IUPAC Longest chain with aldehyde Drop e and add -al Aldehyde takes precedence over all other groups so far Examples

Ketones

Naming:
Drop e, add -one Many common names Simplest is 3 carbons

C.

name: acetone IUPAC: propanone

Ketones
Carbonyl carbon gets lowest number See examples

Common Carbonyl Compounds

Formaldehyde

Manufactured from methanol Used in many polymers


Prepared from ethyl alcohol Formed in the detoxification of alcohol in the liver Formed in the human body as a by-product of lipid metabolism Excreted in the urine Steroid hormones Progesterone/Testosterone

Acetaldehyde

Acetone

Hormones

Physical Properties of Aldehydes and Ketones

Carbon-oxygen double bond is very polar

Affects boiling points More than ethers (C-O bonds) Less than alcohols (C-OH bonds) Low aldehydes very pungent High aldehydes pleasant odors (perfumes)
Similar to alcohols and ethers Soluble up to about 4 carbons Insoluble after that

Odors

Solubility

Preparation of Aldehydes

Oxidation
Leads to carboxylic acid unless care is taken 1 alcohols

Preparation of Ketones
Oxidation of a 2 alcohol Utilizes chromium compounds and sulfuric acid

Chemical Properties of Aldehydes and Ketones


Both under-go combustion reactions Oxidation

Aldehydes can be oxidized, ketones cant See Pg 403

Tollens

reagent Benedicts reagent Fehlings reagent

Chemical Properties of Aldehydes and Ketones

Reduction
Variety of agents can reduce aldehydes and ketones to alcohols NaBH4 and H2 commonly used

Chemical Properties of Aldehydes and Ketones

Hydration
Formaldehyde dissolves readily in water Acetaldehyde somewhat also

Form

hydrates

Chemical Properties of Aldehydes and Ketones

Addition of Alcohols to Carbonyl Groups

Hemiacetal
Aldehyde

+ alcohol

Hemiketal
Ketone

+ alcohol

Not very stable Differs from 1 mol to 2 mol

Chemical Properties of Aldehydes and Ketones

Hemiacetals + HCl = acetal

Hemiketal + HCl = ketal

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