Download Organic Chemistry I Exam Practice: Naming, Groups, Solubility, Reactions, Conformations - and more Exams Organic Chemistry in PDF only on Docsity!
CHE 211 - Organic Chemistry I Lecture Final Exam – Practice Test Question 1 a. Give the IUPAC name of the following molecules. Include R/S, cis/trans, or E/Z notation where applicable. [20 points] i. ii. iii. iv. b. Given here is the structure of Taxol (a potent anticancer drug). Identify the functional groups highlighted. [10 points] c. Rank the following compounds in increasing order of water-solubility. [10 points]
a. When 1 - butene reacts with HBr it produces a racemic mixture of ( R )- 2 - bromobutane and ( S )- 2 - bromobutane. Explain how this racemic mixture is formed using the reaction mechanism. [20 points] b. Give the products and mechanism for the reaction between of chroloethane and sodium borohydride. [20 points]
Fill in the blank boxes with appropriate reagents or compounds. [40 points] a. b. c. d.
a. Answer the following questions on the chair conformations of the molecule given below. i. Draw the two chair conformations of this molecule. Show all bonds including hydrogens on the molecule. [20 points] ii. State which one of the structures drawn in part i) is the most stable form. [10 points] iii. Why did you pick that conformation (in 5.ii) as the most stable chair conformation? [10 points] b. In the space provided draw Newman projections for staggered conformations (do not draw eclipsed conformations) of 1 - chloro- 3 - methylbutane looking down C 2 - C 1. Also, identify each conformation as anti, or gauche where applicable. eye [ 1 0 points]
a. Answer the following questions based on these molecules. i. What are the optically active (chiral) molecules amongst these? [5 points] ii. Identify the pairs of enantiomers if there are any. [5 points] iii. Identify the meso compounds if there are any. [5 points] iv. Identify the sets of diastereomers if there are any. [5 points] b. Given here is the structure of the anticancer drug doxorubicin. i. How many stereocenters does doxorubicin have? Mark each of them on the structure with asterisks (*). [5 points] ii. What is the maximum number of stereoisomers doxorubicin can have? [5 points]
Identify each of these as PROTIC or APROTIC solvents. [ 20 points] a. Methanol - ……………………………. b. Hexane - ……………………………. c. (Ethyl acetate) - ……………………………. d. CH 3 Cl (Chloroform) - ……………………………. e. (1,4-dioxane) - ……………………………. f. (Acetic acid) - ……………………………. g. (Triethylamine) - ……………………………. h. Water - ……………………………. i. (Toluene) - ……………………………. j. CH 3 NO 2 (Nitromethane) - …………………………….
