C=Ofun30 (C=Ofun30.pdf)

C=Ofun30 (C=Ofun30.pdf) - CFQ PP Carbonyl Chemistry...

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CFQ & PP: Carbonyl Chemistry: Fundamentals 165 Reading Brown and Foote: Sections 16.1 – 16.3, 16.5, 17.1, 17.2, 18.1, 18.4 Optional Web Site Reading Carbonyl Group Basics (www.colby.edu/chemistry/OChem/DEMOS/ketones.html) Suggested Text Exercises Brown and Foote: None Optional Interactive Organic Chemistry CD and Workbook Supporting Concepts: Carbonyl Chemistry (p. 70) Concept Focus Questions 1. List at least eight functional groups that contain a carbonyl group. Draw a molecule that contains each functional group on your list. 2. Briefly explain why the carbonyl group can function as both a nucleophile and electrophile. 3. Why do all the functional groups listed in Concept Focus Question 1 undergo somewhat similar reactions? 4. Name and illustrate the three fundamental carbonyl group mechanism steps (or fates). 5. Name and illustrate the two most common generic carbonyl reaction mechanisms. 6. List and explain the four most important factors that control the relative reactivity of a carbonyl-containing functional group in an addition or substitution reaction. 7. What factor controls the mechanistic fate of a tetrahedral intermediate (also called the tetrahedral carbonyl addition compound) that bears a negatively charged oxygen atom? 8. Which is more reactive in nucleophilic addition reactions, aldehydes or ketones? Briefly explain your logic. 9. Arrange the following in order of decreasing reactivity to nucleophilic acyl substitution: Ester, amide, thioester and carboxylate ion. Briefly explain your logic.
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166 Concept Focus Questions Solutions 1. H 3 C H O H 3 C CH 3 O H 3 C OH O H 3 C OCH 3 O H 3 C NH 2 O H 3 C O O O CH 3 H 3 C Cl O H 3 C C N acetaldehyde (an aldehyde) acetone (a ketone) acetic acid (a carboxylic acid) methyl acetate (an ester) acetamide (an amide) acetic anhydride (an acid anhydride) acetyl chloride (an acyl halide) acetonitrile (a nitrile) Nitriles are not carbonyl compounds, but are often included with them because of the similarities in nitrile and carbonyl chemistry. 2. Carbon is less electronegative than oxygen, so the carbonyl carbon bears a δ + while the oxygen bears a δ -. This renders the carbonyl carbon electrophilic. A combination of the oxygen δ -, oxygen lone pairs, and C-O π bond allow the carbonyl group to function as a nucleophile. C O δ + δ - electrophilic carbon nucleophilic oxygen 3. All the functional groups (except nitrile) in Concept Focus Question 1 contain the carbonyl group. Because chemical reactions and many physical properties depend upon interactions and changes in electron density, functional groups with similar electronic structures will have similar chemistry. The nitrile and imine (C=N) functional groups both have polar π bonds ( δ + on carbon, δ - on nitrogen). The carbonyl group is also a polar π bond, so chemical similarities are expected. 4.
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C=Ofun30 (C=Ofun30.pdf) - CFQ PP Carbonyl Chemistry...

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