Aldehydes and ketones
(In this study guide "A" and "K" mean aldehyde and ketone, respectively.)
Priorities: 5 = must know; 4 = very important; 3 = important; 2 = semi-important; 1 = nice but not necessary; read it and learn what you like, but you don't need it; 0 = skip or ignore. The material rated "1" gives you an idea of the relevance of organic chemistry to biology, medicine, Nature, or an idea of the inter-relation of different topics of organic chemistry. I would say most of the "A Word About..." sections fall in this category.
Additional problems: 30(a,b,d,e,f,i), 31(a,b,d,e,i), 32(a-d), 34a, 35, 37(c,d,e,g,h,i,j), 39(c,d), 40, 41, 42, 44(a-d), 52
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Chapter section |
Subject |
Priority |
Item/comments |
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intro |
5 |
Know names in blue and the structures |
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9.1 |
Naming A and K |
5 |
Know IUPAC -al and -one naming; other names to know are formaldehyde, acetone, methyl ethyl ketone (MEK) |
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4 |
Name and structure of benzaldehyde |
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1 |
Names on top of p 251 |
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9.2 |
Some common A and K |
1 |
Uses and production of common aldehydes and ketones |
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9.3 |
Synthesis of A and K |
5 |
Synthesis of A and K by oxidation; Jones' reagent and PCC |
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1 |
Friedel-Crafts acylation |
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0 |
Alkyne + mercuric ion |
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9.4 |
A and K in Nature |
3 |
How A and K are important |
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9.5 |
The carbonyl group |
5 |
Identify A and K functional groups |
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5 |
Geometry of atoms around a carbonyl group; polarization and resonance contributors; reactivity summarized at top of page 256 |
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3 |
Boiling point and solubility characteristics |
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9.6 |
Overview of nucleophilic addition to carbonyl groups |
5 |
Equations 9.8 and 9.9 and discussion are the key to this chapter!!! |
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9.7 |
Addition of alcohols to carbonyl groups |
5 |
Know the acetal and hemiacetal functional groups |
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4 |
Mechanism of acetal and hemiacetal formation |
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5 |
Reversibility of acetal and hemiacetal formation |
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3 |
Cyclic hemiacetals |
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9.8 |
Addition of water |
2 |
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9.9 |
Addition of Grignard reagents and acetylides |
5 |
Know how Grignard and A or K react; alkoxide formed first, then protonation on work-up leads to alcohols |
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5 |
Be able to work backwards---decide how to make a given alcohol from A or K and Grignard reagent |
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9.10 |
Addition of hydrogen cyanide |
3 |
Know what a cyanohydrin is; skip mechanism in equation 9.29 |
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9.11 |
Addition of nitrogen nucleophiles |
5 |
Eq. 9.31 and 9.32 and discussion |
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1 |
Table 9.1 |
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9.12 |
Reduction of carbonyl compounds |
5 |
LiAlH4 and NaBH4 and what they do to A and K; how to make alcohols from A and K |
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9.13 |
Oxidation of carbonyl compounds |
3 |
Aldehyde + Jones' reagent |
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0 |
Tollens' test |
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0 |
Other oxidations of K |
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9.14 |
Keto-enol |
1 |
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9.15, 9.16 |
Acidity of a-hydrogens and deuterium exchange |
1 |
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9.17-9.19 |
Aldol chemistry |
0 |