KETONESBy Emily Smith

and Katie Baba

CONTENTS What are ketones? The structural formula Where they are found (in nature and

products) The naming scheme Some common ketones Synthesis of ketones

WHAT ARE THEY?•Ketones possess at least one carbonyl group, as it is the functional group present in both aldehydes and ketones (a carbon atom double bonded to an oxygen atom).

•http://www.google.ca/imgres?imgurl=http://www.hcc.mnscu.edu/chem/V.21/carbonyl_group.jpg&imgrefurl=http://www.hcc.mnscu.edu/chem/V.21/page_id_43236.html&h=344&w=514&sz=37&tbnid=vGR6DNuOtLGoVM:&tbnh=88&tbnw=131&prev=/images%3Fq%3Dcarbonyl%2Bgroup&zoom=1&q=carbonyl+group&hl=en&usg=__oSRPxRf0jgObObfkvmYdaad88xQ=&sa=X&ei=SNebTLmND82pnQe29rC3DQ&ved=0CCUQ9QEwBA

• Unlike aldehydes hydrogen atoms are never attached to a carbonyl group. •In a ketone the carbon of the carbonyl group is joined to two other carbons.

http://www2.chemistry.msu.edu/faculty/reusch/VirtTxtJml/aldket1.htm

Structural Formula & 3D Structure

http://commons.wikimedia.org/wiki/File:Ketone_structural.png

RCORhttp://commons.wikimedia.org/wiki/File:Acetone-3D-vdW.png

Where are they?

http://www.wekenshop.com/Cosmetics-Fragrances/Nail-Care.html http://www.concessionde

cals.com/fprpopcn.htm

http://commons.wikimedia.org/wiki/File:Testosterone_structure.png

http://passionwind.com/blog/default.asp?archive=1&year=2010&month=5

http://www.seasonedwithlove.com/chocolate_banana_tiramisu.htm

Nail Polis

h

RemoverPo

pcorn

Butter

Flavourin

g

Testo

stero

ne

Bananas

Diabetic Keto

acidosis

’ patie

nt’s

urine

WHERE ARE THEY CONTINUED… Ketones are produced on massive scales in

industries for solvents, and pharmaceuticals (including natural and synthetic steroid hormones)

Molecules of the anti-inflammatory agent cortisone contain three ketone groups.

Nail polish remover is made up of primarily, acetone.

Popcorn butter flavouring used to be made of diketones.

Bananas, apples, cheese, apricot, beef and cauliflower all contain acetophenone.

Fructose, which is found in many foods is also a ketone. Ex) honey, fruit juices

Ketones in Nature

•Ketones are found

EVERYWHERE.

http://www2.chemistry.msu.edu/faculty/reusch/VirtTxtJml/aldket1.htm

Nomenclature of a Ketone•IUPAC Format Ketones end in “one”. (suffix)

•Carbonyl functions can be found throughout a chain or ring.

•Its location is shown by a locator number.

•One begins to number the parent chain from the end with the carbonyl group.

•When the keto group is the only functional group present the number indicating it’s location is placed in front of the root name (i.e. 2-butanone).

•When other functional groups such as multiple bonds are present, the number locating the keto group is placed before the -one (i.e. 4-hexen-2-one).

• Cyclic ketones a number is not given unless more than one carbonyl group is attached.

NOMENCLATURE CONTINUED… The prefix is oxo, (In more complicated molecules with higher

priority functional groups, the keto group is named as an oxo substituent.)

In the case that there are two or more keto groups, this is indicated by a prefix placed in front of the one, along with numbers to locate the positions.

Ex) 2,4-pentadione

http://www.mhhe.com/physsci/chemistry/carey/student/olc/graphics/nomenclature/ketones/ketones-1.html

There are a number of compounds which were named before IUPAC developed the standardized nomenclature rules. Many of these compounds are still referred to by these common names. Ex) acetone, benzophenone.

EXAMPLES OF NAMING SCHEME

http://www2.chemistry.msu.edu/faculty/reusch/VirtTxtJml/aldket1.htm

Simple ketones... No locator number

There are two keto groups (di)

SOME COMMON KETONES… CH3COCH3 known as propanone, acetone, OR

dimethyl ketone

http://molecularmaidens.blogspot.com/

C6H5COC6H5 known as, diphenylmethanone, benzophenone, OR diphenyl ketone

Synthesis/Reaction Properties

http://www2.chemistry.msu.edu/faculty/reusch/VirtTxtJml/aldket1.htm

•There are several ways in which a ketone can be synthesized.

•One way is the oxidation of secondary alcohols

•A hydrogen atom is taken away with two additional electrons

•The hydrogen atom is then separated from the oxygen as a hydrogen ion

•The two hydrogen electrons are used to create the double bond

•Finally, the H (and the two electrons), the H ion, and the oxygen form a water molecule, apart from the newly formed ketone.

Continued...

In an oxidation of secondary alcohols:Oxidizing agent removes hydrogen and electrons from alcoholReacts with them to make ketones and water.

secondary alcohol + (0) --> ketone + HOH