Organic Chemistry 2 - 09Ass#8

Organic Chemistry 2 - 09Ass#8 - Assignment#8 Aldol...

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Assignment #8. Aldol Condensations and Carboxylic Acids. Comments: 1. NOMENCLATURE: As before, the nomenclature on the exam is quite basic. You must be able to recognize and draw the common functional groups and attach typical substituents, Always designate stereochemistry when appropriate. 2. REACTIONS AND REAGENTS: Many of the current questions are review type and thus are duplicates form other assignments. 3. SYNTHETIC SEQUENCES: You should be able to carry out sequences up to 5 steps that involve i) acetylide anions; ii) electrophilic aromatic substitutions; iii) Wittig Reactions; iv) aldol condensations as the key reaction. QUESTIONS: 1. Give the structure of the enolate and the carbonyl compound whose condensation would lead to each of the following primary aldol products. O OH a) O OH H b) OH O c) 2. Predict the major organic product expected When 1a) is treated with NaBH 4 in methanol; b) When 2a) is reacted with CrO 3 in dry pyridine; c) When 2a) is treated with aqueous chromic acid d) when 1c is heated in a high boiling solvent such as toluene [bp = 110 0 C] in the presence of toluene sulfonic acid. 3.
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Organic Chemistry 2 - 09Ass#8 - Assignment#8 Aldol...

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