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04-BS-12: May 2014

Nivaar worked solution (AI-drafted; not reviewed by a licensed engineer)

  1. Question 1 Carbon Classification & Alkene Stability Ranking
  2. Question 2 Benzylic Oxidation & Alkene Addition Reactions
  3. Question 3 Multi-Step Synthesis from Benzene & Cycloalkane Combustion
  4. Question 4 Friedel–Crafts Acylation Mechanism & Alkene Stability
  5. Question 5 Constitutional Isomers of C6H14 & Reaction Classification

Start with Question 1 →

National Exam 04-BS-12, Organic Chemistry — May 2014. 3 hours, closed-book examination; no calculator allowed. Answer ALL FIVE problems; each problem is of equal value (20 points), and the lettered/numbered sub-parts of a given problem may be treated independently.

Reference texts: McMurry, Organic Chemistry, 9th ed. (alkane/carbon classification, alkene stability and E/Z isomerism, electrophilic addition, electrophilic aromatic substitution and benzylic oxidation, Friedel–Crafts acylation, diazonium chemistry, constitutional isomerism).

a meta (1,3) relationship, matching the drawing convention used two questions later for Question 3(a)(i)'s explicitly-labelled meta compound. Solved below as meta; this changes the product from phthalic acid (ortho) to isophthalic acid (meta).