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Ketones

Ketones. By Emily Smith and Katie Baba. Contents. What are ketones ? The structural f ormula Where they are found (in nature and products) The naming scheme Some common ketones Synthesis of ketones. What are they?.

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Ketones

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  1. Ketones By Emily Smith and Katie Baba

  2. Contents • What are ketones? • The structural formula • Where they are found (in nature and products) • The naming scheme • Some common ketones • Synthesis of ketones

  3. 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

  4. Structural Formula & 3D Structure http://commons.wikimedia.org/wiki/File:Ketone_structural.png RCOR http://commons.wikimedia.org/wiki/File:Acetone-3D-vdW.png

  5. Where are they? http://commons.wikimedia.org/wiki/File:Testosterone_structure.png http://www.wekenshop.com/Cosmetics-Fragrances/Nail-Care.html http://www.concessiondecals.com/fprpopcn.htm Diabetic Ketoacidosis’ patient’s urine http://www.seasonedwithlove.com/chocolate_banana_tiramisu.htm Bananas Popcorn Butter Flavouring Nail Polish Remover Testosterone http://passionwind.com/blog/default.asp?archive=1&year=2010&month=5

  6. 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

  7. Ketones in Nature • Ketones are found EVERYWHERE. http://www2.chemistry.msu.edu/faculty/reusch/VirtTxtJml/aldket1.htm

  8. 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.

  9. Nomenclature Continued… • The prefix is oxo, (In more complicated molecules with higher priority functional groups, the keto group is named as an oxosubstituent.) • 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.

  10. Simple ketones... No locator number EXAMPLES OF NAMING SCHEME  There are two ketogroups (di) http://www2.chemistry.msu.edu/faculty/reusch/VirtTxtJml/aldket1.htm

  11. Some Common Ketones… • CH3COCH3 known as propanone, acetone, OR dimethylketone • http://molecularmaidens.blogspot.com/ • C6H5COC6H5 known as, diphenylmethanone, benzophenone, OR diphenylketone

  12. 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/aldket1.htm

  13. 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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