Al-Imam Muhammad ibn Saud University

College of Science Student’s Name: ……………………………………………… ID ……………

Department of Chemistry

Examination # 1
CHEM 327 – Organic Reaction Mechanisms (1st Semester 1443)
Question #1: For the following transformation, Supply the missing charges and Lone pairs: [3pts]

Question #2: For the following steps, Use curved arrows to show the movement of electrons for
bond-breaking and bond-making: [2 pts]

Question #3: answer the questions from A through E [7 pts]

(A) The following mechanism for the hydrolysis of methyl acetate in a strong base is consistent with the
experimental data for the reaction.

all of the charged species in this mechanism are …………………………………………..……….. because the reaction
occurs in ……….........................
(B). Number all relevant non-hydrogen atoms in the starting materials, and number the same atoms in the
product.

(C ). In the following reaction, First step is removal proton by strong base. Circle the proton that most likely to
be removed in the starting materials?

(D). For the following reaction, indicate the Nucleophile, Electrophile, and the Leaving group:

(E). For the following mechanism, Fill-in-the blank the missing intermediates:

Question #4: write step-by-step mechanism for the following reactions: [8 pts]

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