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2444-102111 - QUIZ 5 Avg Stnd Dev 19.8 25 6.3 2 Chapter 19...

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QUIZ 5 Avg. 19.8 / 25 Stnd. Dev. 6.3
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Chapter 19. Reduction 2 • If an oxidation involves the loss of two electrons, a reduction involves the gain of two electrons. • The structural changes in the reduction product are often measured by whether hydrogen is gained and or if an oxygen atom is lost.
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To begin, you should know: 3 • The basic rules of nomenclature for alcohols, aldehydes, ketones, carboxylic acids, and carboxylic acid derivatives. (chapter 5, sections 5.6, 5.9) • Bond polarization. (chapter 3, section 3.7) • The CIP rules for prioritizing substituents, groups and atoms. (chapter 9, section 9.3) • Lewis acids and Lewis bases. (chapter 6, section 6.5) • Energetics and transition states. (chapter 7, sections 7.5, 7.6) • Rotamers and conformations. (chapter 8, sections 8.1, 8.4) • Chirality, enantiomers and diastereomers. (chapter 9, sections 9.1, 9.5) • Alkene stereoisomers. (chapter 9, section 9.4) • The fundamental reactivity of alkenes. (chapter 10, sections 10.2, 10.3, 10.4) • The fundamental reactivity of carbonyl compounds. (chapter 16, sections 16.3 and 16.7; chapter 18, section 18.1) • How to identify acyl addition reactions with strong and weak nucleophiles. (chapter 18, sections 18.3, 18.4, 18.5, 18.6, 18.7) • The fundamentals of electron transfer for an oxidation. (chapter 17, section 17.1) • The reagents used to oxidize an alcohol to an aldehyde or ketone. (chapter 17, section 17.2) Oxidation reactions of alkenes. (chapter 17, section 17.3)
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When completed, you should know: 4 A reduction is defined as the gain of electrons, or the gain of hydrogen atoms. • Both sodium borohydride and lithium aluminum hydride reduce ketones or aldehydes to alkoxides, and hydrolysis gives the alcohol. Lithium aluminum hydride is a more powerful reducing agent than sodium borohydride. • Lithium aluminum hydride will reduce acid derivatives to the corresponding alcohol and an amide to an amine. Nitriles are also reduced to an amine. • In the presence of a transition metal catalyst, hydrogen gas converts an alkene to an alkane, an alkyne to an alkene. Hydrogenation of an alkyne with palladium in the presence of quinoline gives the Z-alkene in what is known as Lindlar reduction. • In the presence of a transition metal catalyst, hydrogen gas converts a ketone or aldehyde to an alcohol. • Acid chlorides can be reduced by catalytic hydrogenation to give an aldehyde in what is called the Rosenmund reduction. Nitriles are reduced by catalytic hydrogenation to a primary amine.
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