Caada College

J. Medina

Chemistry 232
Organic Chemistry II
Chapter outlines
Based on Wade, 7th edition

Spring 2015

Chapter 18: Ketones and Aldehydes

1. What is the general structure of a ketone and of an aldehyde? How are these structures similar and different?
2. Get familiar with all the carbonyl compounds listed in table18.1.
3. What is the hybridization of the carbonyl group? What is its shape? Are they chiral? Are the pro-chiral?
4. Are carbonyl compounds polar? Can they form hydrogen bonding? Show how?
5. In the IUPAC name of open chain ketones, the ending e of alkane is replaced by the ending one for ketone. The
location of the carbonyl group is given the smallest possible number according to its position in the chain. The
carbonyl group in cyclic ketones always gets number 1. The substituent name of ketones is oxo. Common names of
ketones are also found: list the names of the two groups attached to the carbonyl group followed by the word ketone.
6. In the IUPAC name of open chain aldehydes, the ending e of alkane is replaced by the ending al of aldehydes. For
cyclic molecules referring to the aldehyde as the main functional group, name the ring followed by the word
carbaldehyde. An aldehyde group as a substituent is named formyl. Common names are also available but more
difficult to figure out that the ones for ketones.
7. When a molecule contains both a ketone and an aldehyde group, the aldehyde gets priority as the main functional
when naming the molecule.
8. Work on problems 18.1 and 18.39 to practice naming. We will check the answers in class.
9. Reviewing spectroscopy. This will be particularly useful to students taking the lab when they need to identify their
unknowns. IR: What are the typical; absorption bands of aldehydes and ketones. Where do they show on the IR
spectrum (wavenumber). Proton NMR: What are the specific structural characteristics of each functional group that
could be observed on their corresponding 1H NMR spectra? Skip the MS and UV sections.
10. Syntheses of aldehydes and ketones (REVIEW): Primary alcohols to aldehydes with PCC; secondary alcohols to
ketones with several oxidizing agents; aldehydes to ketones via Grignard and oxidation; aldehydes and ketones can be
prepared from alkenes via ozonolysis with O3; phenyl ketones and aldehydes can be made by Friedel Crafts acylation;
oxymercuration and hydroboration reactions of alkynes.
11. Work on problem 18.6 to be discussed in class.
12. New synthetic methods: Use of 1,3-dithianes; ketones from the reaction of carboxylic acids with organolithium
compounds; from the reaction of nitriles with Grignard reagents; aldehydes from the reduction of carboxylic acids or
acid chlorides; ketones from the reaction of acid chlorides with Grignard reagents or Gilman reagents.
13. To help with all of the available reactions to make aldehydes and ketones, carefully inspect the summary that starts on
page 828. Search the internet or in your book for the reaction mechanisms. Finally, work on problems 18.6 to 18.11.
14. One of the most common reaction of ketones and aldehydes is nucleophilic addition. There are several examples of
this type of reaction in acid conditions and basic conditions. Review the key mechanism 18.1, then review several
related mechanisms as part of specific reactions: hydration (18.14); formation of cyanohydrins (18.15); formation of
imines (18.16); formation of oximes, hydrazones and semicarbazones (18.17); formation of acetals (18.18); Hydride
reductions (18.21). Review all these sections to identify the nucleophile in each of the reactions. Make a complete
summary table by adding the missing information to summary in page 846.
15. Other reactions of aldehydes and ketones: the Wittig reaction, an aldehyde or ketone is reacted with a phosphorus
ylide to give an alkene and triphenylphosphine oxide through a betaine intermediate. The nucleophile in this reaction
is the ylide. The use of acetals as protecting agents and the oxidation of aldehydes are other reactions to consider.
Suggested practice problems
39, 41, 44, 48, 50, 51, 56, 59, 61, 62, 63, 64, 65

Jeanette Medina