Organic Chemistry Exam Review: Nomenclature, Theory, Reactions, Mechanism, Synthesis - Pro, Exams of Organic Chemistry

Download Organic Chemistry Exam Review: Nomenclature, Theory, Reactions, Mechanism, Synthesis - Pro and more Exams Organic Chemistry in PDF only on Docsity! Page 1 of 7 I. Nomenclature 1. Draw structures for the following compounds: (5 points) $-butyrolactam phthalic acid 2. Provide common names for each structure below. (5 points) 3. Give IUPAC names for each of the following structures. (6 points) II. Theory 1. Which of the following substances would function best as soap? (2 points) a) a triester b) decanoic acid c) sodium decanoate d) sodium benzoate 2. Predict the pKa of each indicated H within 2 pKa units. (6 points) Page 2 of 7 3. Circle all structures that are derivatives of a carboxylic acid. (4 points) 4. The Fischer esterification reaction can be best categorized by which of the following mechanism types? (3 points) a) SN2 b) addition-elimination c) elimination-addition d) SN1 5. In each series, circle the structure that is most reactive toward nucleophilic attack. (4 points) 6. Indicate the sequence that correctly lists the compounds below in order of increasing boiling points. (3 points) a) 1-2-3 b) 2-3-1 c) 3-1-2 d) 3-2-1 e) 2-1-3 f) 1-3-2 7. Show three different methods for synthesizing benzoic acid from three different starting materials that are not derivatives of a carboxylic acid.(6 points) Page 5 of 7 IV. Mechanism 1. Show a detailed arrow pushing mechanism for the reaction below. Include all intermediate structures and formal charges. (12 points) 2. Since the stability of the products are equivalent to the stability of the starting materials, how could this reaction be driven toward the products. (3 points) Page 6 of 7 V. Synthesis 1. Show all steps that are necessary to complete the synthesis below. (5 points) 2. Fill in the missing starting materials and reagents. (9 points) Page 7 of 7 VI. Extra Credit (5 points possible) Complete the following transformation by filling in the necessary reagents. (Hint: Step 1: a boys name; Step 2: “To make smaller” or a color of an apple is abbr. for this step; Step 3: “Ring around the Rosies”) On exam 4 you received _________ points out of 100 points possible. To check your overall lecture grade go to http://courses.weber.edu.