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Chemistry 242
Exam #4
Summer 2010
The second exam will be given on Tuesday Aug. 3, covering material in Chapters 19, 20, and 21 in the
text. The test will cover carbonyl compounds.
The following textbook sections will NOT be covered on the exam:
19.9. 19.13 – 19.15
20.5
21.8 21.9
It is particularly important to study and do the problems for the following sections:
19.4
19.8 19.11
20.4 20.6
21.2 21.3 21.6
Know the following reaction mechanisms:
Acetal formation (acid catalyzed)
Fisher esterification (acid catalyzed)
Ester hydrolysis (acid catalyzed)
Nucleophilic acyl substitution (up-down-out) Example: acid chloride + alcohol to give ester
Ester reaction with Grignard reagents
Questions that may be on the exam:
What is the proper name for this aldehyde/ketone/carboxylic acid/acid chloride/anhydride/ester?
Which carboxylic acid is most acidic? (Which one forms the most stable anion?) Why?
Which of the carboxylic acid derivatives (acid chloride, acid anhydride, ester, amide) is the
most stable? Which is the most reactive? Why are acid chlorides highly reactive?
What is the mechanism for nucleophilic acyl substitution?
Why do carboxylic acids generally not undergo the “up-down-out” mechanism?
How would you prepare this ester, starting from methane?
How would you protect a ketone group in a synthesis problem?
How can you use the Wittig reaction to make an alkene?
NMR – give structure of C6H12O2 with the following NMR spectrum. What is degree of unsat?
What do PCC, CrO3, SOCl2, NaBH4, LiAlH4, Ph3P=CH2, Mg, CO2 do?
Topics on the exam:
Prep. of aldehydes and ketones: alcohol oxidation (PCC/CrO3) and ozonolysis
Rxn of aldehydes and ketones: reduction, Grignard reaction, acetal formation,
Wittig reaction, hydration
Preparation of carboxylic acids: oxidation of 1° alcohols, Grignard reaction w/ CO2
nitrile hydrolysis, hydrolysis of all carboxylic acid derivs.
Reaction of carboxylic acids:
deprotonation with base, reduction (LiAlH4 only),
SOCl2 reaction making acid chlorides
acid-catalyzed ester formation (Fisher Esterification)
Preparation of anhydrides:
condensation of carboxylic acids
carboxylate anion + acid chloride
Rxn anhydrides/acid chlorides: react w/ many nucleophiles by the up-down-out mechanism
Prep. of esters and amides:
reaction with acid chlorides, reaction with anhydrides,
rxn of carboxylic acids with an alcohol (H+ cat., ester only)
Reaction of esters and amides:
hydrolysis (to carboxylic acid), reduction (LiAlH4 only),
Grignard reaction
Preparation of nitriles:
reaction of :CN- anion w/ RCH2X (SN2)
Reaction of nitriles:
reduction w/ LiAlH4 to 1° amine; hydrolysis to carboxylic acid
For aldehydes, ketones, esters, amides, and acid chlorides: Nucleophile Attacks Carbonyl Carbon
For carboxylic acids, the nucleophile/base usually deprotonates to form a carboxylate anion
Know how to do synthesis problems, starting from an alkane.