Download Exam 2

CHEM 243 STUDY GUIDE for EXAM #2
Exam: 10am & 1 pm sections: Thursday, May 19.
New Format! For this exam you will be allowed to have one 8x11 page of notes—Front only,
nothing on the back. You can put any information you want on this sheet. Review the study
guide below to help decide what you want to put on this. You will turn this sheet in with the
exam but it will not be graded, I’m curious to what you wrote down.
One of you extra credit questions will be if you feel creating your notes had any positive
effects in your study of the material as compared without having the notes? you can write this up
ahead of time.) Along with written comment judge this on a scale from 1-10 (10=very
helpful/positive, 1=useless, detrimental).
The exam will be over selected sections of chapters 17, 18, and a section 11.5. The best items to
study and review are in-class assignment #2 (mechanisms questions will come from this),
problem sets (on website) and problem from the text (listed below).
Extra Office hours: Thurs 8:30-10, 11:30-1 pm.
Sections to focus on: Chap 17: 17-10-17.12 and 17.16. Chap 18: 18.1-18.2, 18.6, 18.9-18.18.
Chap 11 11.5 only—oxidation of alcohols
Problems from the text: Chap 17: 33, 34, 40, 42, 49 Chap 18: 1, 2, 20, 22, 23, 26, 27-29, 32-34,
37, 40 Chap 11: 20
Reactions (& mechanisms) to Know:
Acid catalyzed:
Formation of an imine from a carbonyl and a primary amine (know mechanism)
Formation of enamine from carbonyl and secondary amine (know mechanism)
Actetal and Ketal formation and hydrolysis of acetals and ketals (know mechanism)
Base catalyzed
Michael reaction enolate attack of unsaturated carbonyl. (know mechanism)
Alkylation of carbonyls using LDA sec 18.7. Know structure of LDA
Aldol Addition and dehydration (aldol condensation).sec 18.10-11 (know mechanism)
Claisen Condensation sec 18.13 (know mechanism).
Intramolecular condensations, (Know mechanisms) sec 18.15
Decarboxylation of 3-oxocarboxylic acids 18.17 (know mechanism)
Malonic Ester/Acetoacidic ester synthesis 18.18-18.19 (know mechanisms of all steps)
Misc
Wittig Reaction sec 17.16 see problem 49 chap 17
Acidity of the alpha Hydrogens of carbonyls. 18.1 Understand (Ka values) of table 18.1.
Know when an acid will be completely deprotonated by hydroxide ion or LDA.
Enol Tautomers 18.2. Be able to draw an enol of an aldehyde or ketone.
Oxidation states: Be familiar with the various oxidation states of Carbon. Which states are high
potential energy (fuels) and which are low potential Energy. Know if a certain reaction is an
oxidation or a reduction of the organic compound (e.g a ketone being converted to an alcohol is a
reduction)
Oxidation of alcohols & aldehydes using sodium dichromate. 11.5 You do not need to know
the mechanisms.
NADH and NAD+ as biological reducing/oxidizing agents see section 24.1 You do not need to
memorize the structures but know and recognize the ‘business end’ of the molecules. Draw the
mechanism for how they reduce and oxidize.