Week 1 Objectives

Week 1 Objectives - • Draw the mechanism and show the...

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Page 1 of 1 Organic Chemistry II UC-Berkeley Extension, Fall 2011 August 29, 2011 Week 1: Aldehydes & Ketones: the carbonyl group, nomenclature, physical properties, reaction themes, reactions with carbon nucleophiles, Wittig reaction, hydrates, hemiacetals, acetals, acetals as protecting groups, imines/Schiff bases Objectives: Describe basic structure of the carbonyl functional group. Describe the structure of aldehydes and ketones. Using IUPAC nomenclature, provide the correct name of an aldehyde or ketone, and draw the corresponding structure based on a chemical name. Correctly name compounds substituted with multiple functional groups. Describe the intermolecular forces exhibited by aldehydes and ketone and how they determine the physical properties (specifically, boiling points and water solubility) of these compounds. Describe the two common reaction/mechanism themes seen throughout carbonyl chemistry (i.e. addition of a nucleophile and role as a Lewis base).
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Unformatted text preview: • Draw the mechanism and show the resulting products of a carbon nucleophile (Grignard reagent, organolithium, terminal alkyne, or cyanide) reacting with an aldehyde or a ketone. • Describe the importance of carbon nucleophiles reacting with aldehydes and ketones as a key method for making new carbon-carbon bonds. Show how alkynes in particular can undergo further reactions resulting in useful products. • Draw the mechanism and show the resulting products of a Wittig reaction (addition of a phosphonium ylide to an aldehyde or ketone). • Draw the products of the reaction of a phosphonoester with strong base and an aldehyde or ketone (Horner-Emmons-Wadsworth). • Draw the mechanisms showing how hemiacetals and acetals can be formed from an aldehyde or a ketone. • Show how sugars can exist as straight chain aldehydes or as cyclic hemiacetals....
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