Quiz # 3 (Chp.

4)
KCHM 412- Organic Reactions Mechanisms
Student's Name: ………………………………………………………… ID: ……………………………. Date: …./…../……..

1. Rank the stability of the following carbocations.

+
CH2
+ O
H3C CH
+
+ C +
CH3 CH3 H3C H3C CH2

…………………………………………………………………………………………………………………..

…………………………………………………………………………………………………………………..

…………………………………………………………………………………………………………………..

2: Complete the missing steps of formations of carbocations:

3: Rearrangement of a carbocation frequently involves (1) ………………………….,

(2) ………………………, or (3) …………………………… to the carbocation from an adjacent
carbon (a 1,2-shift).

4: Complete the following mechanistic steps (Alkyl shift)?

5. Write step-by-step mechanism of the following transformations:

……………………………………………………………………………………………………..
……………………………………………………………………………………………………..
……………………………………………………………………………………………………..
……………………………………………………………………………………………………..
……………………………………………………………………………………………………..
……………………………………………………………………………………………………..
……………………………………………………………………………………………………..
……………………………………………………………………………………………………..
……………………………………………………………………………………………………..
……………………………………………………………………………………………………..
……………………………………………………………………………………………………..
……………………………………………………………………………………………………..

……………………………………………………………………………………………………..
……………………………………………………………………………………………………..
……………………………………………………………………………………………………..
……………………………………………………………………………………………………..
……………………………………………………………………………………………………..
……………………………………………………………………………………………………..
……………………………………………………………………………………………………..
……………………………………………………………………………………………………..
……………………………………………………………………………………………………..
……………………………………………………………………………………………………
…………………………………………………………………………………………………….

……………………………………………………………………………………………………..
……………………………………………………………………………………………………..
……………………………………………………………………………………………………..
……………………………………………………………………………………………………..
……………………………………………………………………………………………………..
……………………………………………………………………………………………………..
……………………………………………………………………………………………………..
……………………………………………………………………………………………………..
…………………………………………………………………………………………………….