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TASK 3: Read reading material no. 3 and complete the mind map below by following the legends below as your guide. Ketone properties synthesis uses Biological Chemical industry Medicinal Legend: Name ketone's functional group and its respective suffix. Give at least 6 sites where ketone biologically occur Cite at least 5 industrial materials that contain ketone and its uses. Provide IUPAC ketone names according increasing carbon-chain (3-7). Explain the medicinal ketone mentioned in the reading material. 15

READING MATERIAL No. 3 (Ketone) A ketone is either the functional group characterized by a carbonyl group (O=C) linked to two other carbon atoms or a chemical compound that contains this functional group. A ketone can be generally represented by the formula: O O= R Ketone Figure 3.1. Structure of ketone group A carbonyl carbon bonded to two carbon atoms distinguishes ketones from carboxylic acids, aldehydes, esters, amides, and other oxygen-containing compounds. The double-bond of the carbonyl group distinguishes ketones from alcohols and ethers. The simplest ketone is acetone (also called propanone). The carbon atom adjacent to a carbonyl group is called the a-carbon. Hydrogens attached to this carbon are called a-hydrogens. In the presence of an acid catalyst the ketone is subjected to so-called keto-enol tautomerism. The reaction with a strong base gives the corresponding enolate. A diketone is a compound containing two ketone groups. In general, ketones are named using IUPAC nomenclature by changing the suffix - e of the parent alkane to -one. For common ketones, some traditional names such as acetone and benzophenone predominate, and these are considered retained IUPAC names, although some introductory chemistry texts use names such as propanone. Oxo is the formal IUPAC nomenclature for a ketone functional group. However, other prefixes are also used by various books and journals. For some common chemicals (mainly in biochemistry), keto or oxy is the term used to describe the ketone (also known as alkanone) functional group. Physical properties A carbonyl group is polar which makes ketones polar compounds. The carbonyl groups interact with water by hydrogen bonding; hence ketones are soluble in water. It is a hydrogen-bond acceptor, but not a hydrogen-bond donator, and cannot 16

hydrogen-bond to itself. This makes ketones more volatile than alcohols and carboxyllc acids of similar molecular weight. Synthesis Ketones can be created by QAIQQEQD of secondary W. The process requires a strong oxidizing agent such as potassium permanganate, potassium dichromate or other agents containing gerI). The alcohol is oxidized by heating under reflux in acidified solution. For example propan-2-ol is oxidized to propanone [ggetqlle]: H3C—CH{OH)—CH3 _. H3C—CO—CH3 Acetone. acetoacetate and beta-hydroxybufyrate are ketones or ketone bodies generated from carbohydrates. fatty acids and amino acids in humans and most vertebrates. Ketones are elevated in blood after fasting including a night of sleep. and in both blood and urine in starvation. hypoglycemia due to causes other than hyperinsulinism. various inborn errors of metabolism, and ketoacidosis (usually due to diabetes mellitusl. Acetoacetate and beta-hydroxybutyrate are an important fuel for many tissues. especially during fasting and starvation. The brain. in particular. relies heavily on ketone bodies as a substrate for lipid synthesis and for energy during times of reduced food intake. Ketone compounds have important physiological properties. They are found in several sugars and in compounds for medicinal use. including natural and synthetic steroid hormones as well as a cure to opiates addiction with the help of the ketone methadone [C21H27NO]. Some common opiates are heroin, opium. and morphine. All these drugs work by causing the body to release excessive amounts of the hormone dopamine. To help combat opiate addiction. the oral medication methadone can be prescribed by a medical professional. Methadone works by binding to the dopamine receptor in the brain. This eliminates the user's physical dependence on opiates because the user does not need anything else to bind to the dopamine receptor. It also prevents the feelings of happiness caused by heroin because the dopamine has nowhere to attach to. This usually eliminates the user's desire for heroin as well. Methadone is also able to suppress withdrawal symptoms for 24 - 36 hours. Only a small number of ketones are manufactured on a large scale in industry. They can be synthesized by a wide variety of methods. and because of their ease of preparation. relative stability. and high reactivity. they are nearly ideal chemical intermediates. Many complex organic compounds are synthesized using ketones as building blocks. They are most widely used as solvents. especially in industries manufacturing explosives. lacquers. paints. and textiles. Ketones are also used in tanning. as preservatives. and in hydraulic fluids. 17 .. _.'..' Combined with other functional group, ketones are widespread in nature. Compounds such as cinnamaldehyde (cinnamon bark). vaniliin (vanilla bean). Citra {lemongrass}. helminthosporal (a fungal toxin). carvone (Spearmint and caraway). camphor (camphor trees] are found chiefly in microorganisms or plants. Whereas. compounds such as muscone (musk deer). testosterone [male sex hormone}, progesterone [female sex hormone}, cortisone (adrenal hormone) have animal and human origin.

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TASK 3: Read reading material no. 3 and complete the mind map below by following the legends below as your guide. Ketone properties synthesis uses...
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