Ketones - SanfordChemistry

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By Emily Smith
and Katie Baba
 What
are ketones?
 The structural formula
 Where they are found (in nature and
products)
 The naming scheme
 Some common ketones
 Synthesis of ketones
•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_s
tructural.png
http://commons.wikimedia.org/wiki/File:Acetone-3D-vdW.png
Where are they?
http://commons.wikimedia.or
g/wiki/File:Testosterone_struc
ture.png
http://www.wekenshop.com/
Cosmetics-Fragrances/NailCare.html
http://www.concessiondec
als.com/fprpopcn.htm
http://www.seasonedwithlov
e.com/chocolate_banana_tira
misu.htm
http://passionwind.com/blog/
default.asp?archive=1&year=20
10&month=5
 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
http://www2.chemistry.msu
.edu/faculty/reusch/VirtTxt
Jml/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-2one).
• Cyclic ketones  a number is not given unless more than one carbonyl
group is attached.

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.
Simple
ketones...
No locator
number
EXAMPLES
OF
NAMING
SCHEME
 There are two keto
groups (di)
http://www2.chemistry.ms
u.edu/faculty/reusch/VirtT
xtJml/aldket1.htm



CH3COCH3 known as propanone, acetone, OR dimethyl
ketone
http://molecularmaidens.blogspot.com/
C6H5COC6H5 known as, diphenylmethanone,
benzophenone, OR diphenyl ketone
Synthesis/Reaction
Properties
•There are several
ways in which a
ketone can be
synthesized.
•One way is the
oxidation of
secondary alcohols
http://www2.chemistry.msu.edu/
faculty/reusch/VirtTxtJml/aldket
1.htm
Continued...
•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.
In an oxidation of secondary
alcohols:
Oxidizing agent removes
hydrogen and electrons from
alcohol
Reacts with them to make
ketones and water.
secondary alcohol + (0) --> ketone + HOH
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