CHEM263 Midterm: CHEM 263 UofA Chem163 Midterm 1997
CHEM 163 MIDTERM
February 13, 1997
Dr. John C. Vederas
I. Structure and Nomenclature - 43 Points -
A. Draw structures for which names are given, or name the given structures by any correct (systematic or
common) nomenclature. Be sure to give cis or trans (or if appropriate Z or E) or R or S assignment to the
isomer where indicated by asterisks (***). (2 points each - 20 points total)
1. ethylene glycol (antifreeze constituent)
2. toluene (used as solvent in glue)
3. (explosive in match heads)
2,4,6-trinitrophenol or picric acid (or name as a hydroxybenzene)
4. (S)-trans-2-phenyl-3-dodecene
5. commonly used as a base or solvent
pyridine
6. (common lubricant, also occurs in cells)
glycerol or 1,2,3-propanetriol or will accept 1,2,3-trihydroxypropane
7. Available in Safeway as a food additive
vanillin or 4-hydroxy-3-methoxybenzaldehyde
8. trans-1,11-tridecadiene-3,5,7,9-tetrayne (flower colour in dahlias)
9. para-aminobenzoic acid (a key bacterial product necessary for folic acid synthesis - sulfa
drugs mimic this compound)
10. sperm attractant for coral polyps
2,4-tetradecadiyne-1-ol
B. Determine whether the following pairs of structures are identical (i.e. different pictures of the same
molecule), structural isomers, diastereomers, or enantiomers. (2 points each - 8 pts total).
1.
diastereomers
2.
structural isomers
3.
identical
4.
Document Summary
Dr. john c. vederas: structure and nomenclature - 43 points , draw structures for which names are given, or name the given structures by any correct (systematic or common) nomenclature. 2,4-tetradecadiyne-1-ol: determine whether the following pairs of structures are identical (i. e. different pictures of the same molecule), structural isomers, diastereomers, or enantiomers. (2 points each - 8 pts total). 4. diastereomers structural isomers identical identical: 1. Cortisone is a natural adrenocorticoid hormone that has anti-inflammatory properties. False: cortisone has the same number of carbons as the pregnancy hormone, progesterone. True: a human produces about 1 milligram of male or female sex hormone per day. True: cholesterol is made in the body by humans. True: the difference between androgen and estrogen skeletons is one methyl group. Physical properties and reactivity - 13 points: it would be predicted that one of the two phenolate anions shown below would form more readily and be more stable.
