Chapter 18 Handouts

Chapter 18 Handouts - Chapter 18 Ketones and Aldehydes...

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Chapter 18 Ketones and Aldehydes
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Chapter 18 2 Carbonyl Compounds =>
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Chapter 18 3 Carbonyl Structure • Carbon is sp 2 hybridized. • C=O bond is shorter, stronger, and more polar than C=C bond in alkenes. =>
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Chapter 18 4 IUPAC Names for Ketones • Replace - e with – one (alk ane becomes alkan one ). Indicate the position of the carbonyl with a number. • Number the chain so that carbonyl carbon has the lowest number. • For cyclic ketones the carbonyl carbon is assigned the number 1. =>
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Chapter 18 5 Examples CH 3 C O 3 3 O Br 3 C O 3 2 OH 3-methyl-2-butanone (3-methylbutan-2-one) 3-bromocyclohexanone 4-hydroxy-3-methyl-2-butanone (4-hydroxy-3-methylbutan-2-one) =>
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Chapter 18 6 Naming Aldehydes • IUPAC: Replace - e with - al . • The aldehyde carbon is number 1. • If -CHO is attached to a ring, use the suffix - carbaldehyde . =>
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Chapter 18 7 Examples CH 3 2 3 2 O CHO 3-methylpentanal 2-cyclopentenecarbaldehyde =>
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Chapter 18 8 Name as Substituent • On a molecule with a higher priority functional group, C=O is oxo - and -CHO is formyl. • Aldehyde priority is higher than ketone. CH 3 CC H 3 2 O O COOH CHO 3-methyl-4-oxopentanal 3-formylbenzoic acid =>
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Chapter 18 9 Common Names for Ketones • Named as alkyl attachments to -C=O. • Use Greek letters instead of numbers. CH 3 C O 3 3 3 C O 3 3 Br methyl isopropyl ketone α− bromoethyl isopropyl ketone =>
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Chapter 18 10 Historical Common Names CH 3 C O 3 C 3 O C O acetone acetophenone benzophenone =>
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Chapter 18 11 Aldehyde Common Names • Use the common name of the acid. • Drop - ic acid and add - aldehyde . ¾ 1 C: formic acid, formaldehyde ¾ 2 C’s: acetic acid, acetaldehyde ¾ 3 C’s: propionic acid, propionaldehyde ¾ 4 C’s: butyric acid, butyraldehyde. =>
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Chapter 18 12 Boiling Points • More polar, so higher boiling point than comparable alkane or ether. • Cannot H-bond to each other, so lower boiling point than comparable alcohol. => Handout p.1
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Chapter 18 13 Solubility • Good solvent for alcohols. • Lone pair of electrons on oxygen of carbonyl can accept a hydrogen bond from O-H or N-H. • Acetone and acetaldehyde are miscible in water. =>
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Chapter 18 14 Formaldehyde • Gas at room temperature. • Formalin is a 40% aqueous solution. O C O C O C H H H H H H heat HC O H H 2 O H OH HO trioxane, m.p. 62 ° C formaldehyde, b.p. -21 ° C formalin =>
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Chapter 18 15 IR Spectroscopy • Very strong C=O stretch around 1710 cm -1 .
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Chapter 18 Handouts - Chapter 18 Ketones and Aldehydes...

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