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(CHEM111)[2002](s)quiz3~1463^_10039.pdf
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V3.1
Quiz #3, CHEM 111, Fall Semester, 2002/2003
Student Name: Student ID #: Section:

Note: You are required to complete all questions independently. Reference materials and textbook are prohibited. Total marks for this quiz are 50 points.
Question 1: Name FIVE each of nucleophiles and electrophiles from the following reagents. Underline the atom which acts as nucleophile or electrophile. For example: H3N is a nucleophile (10 points)

(CH3)2 CO H3CCH2 O HOH BBr3 H3CCH2 Br Me2S HF
Answer:
Nucleophiles:

Electrophiles:
Question 2: Calculate the degree of unsaturation in the formula of C6H10ClNO and draw FOUR possible structures possessing different carbon skeleton. (10 points)
Answer:
Question 3: Use the correct arrows to indicate the movement of electrons and predict the major product in the following reaction (10 points)
Answer:

+ HCl


1

V3.1

Question 4: 2-Chloro-2-methylpropane reacts with water in three steps to yield 2-methyl-2-propanol. The first step is slower than the second, which in turn is much slower than the third. The reaction takes place slowly at room temperature, and the equilibrium constant is near 1. Draw a reaction energy diagram, labeling all points of interest and making sure that the relative energy levels on the diagram are consistent with the information given. (15 points)
CH3
CH3 CH3
CH3

H
H2O
H2O
H3CC Cl

H3CC

H3CC O


H3CCOH +H3O
+ Cl
H
CH3
CH3 CH3
CH3
Answer (complete the energy diagram in the box provided below):

Reaction progress

Question 5: Draw the line-bond (Kekul) structures of the following molecules. (5 points)
(A) 4-tert-Butyl-2-methylheptane (B) trans-2,3,3-Trimethyl-1,4-octadiene Answer: (A) (B)
2