KING FAHD UNIVERSITY OF PETROLEUM AND MINERALS

CHEMISTRY DEPARTMENT
Organic 201 - CHAPTER 18

STUDENT’S NAME: ID NUMBER:

Q1: What is the best name for the following Q4: What is the crucial intermediate with
compound? the correct mechanistic arrows for the
O acidic cleavage of the ether shown below?
HI
O H2O
1. isopropoxybutane
2. butyl isobutyl ether
3. 2-butoxypropane
4. butyl propyl ether
5. butyl isopropyl ether

Q2: What is the most likely product of the

following reaction

(CF3CO2)2Hg NaBH4 Q5: What is the major organic Product of

OH
the reaction shown below?
THF ?
1. CH3MgBr
O
2. H3O+

Q3: What is the major organic product of the

reaction shown below?
1. MCPBA Q6 What is the product of Claisen
rearrangement of the 2-butenyl phenyl
2) HBr, Et2O
ether shown below?
O
Q7: Which group of reagents will Q9: What is the product of the following
accomplish the transformation shown sequence of reactions?
below? S

Br H2N NH2 NaOH

OCH3
H2O
and enantiomer  
Br
 
H  
 
1. NBS/CH3OH/DMSO
2. OsO4/pyridine followed by HBr,
followed by NaOH, followed by
CH3I
3. Br2 followed by CH3ONa
4. MCPBA followed by HBr
followed by NaOH
5. Hg(OAc)2/CH3OH followed by
HBr

Q8: Z-2-Butene reacts with Br2/H2O
followed by methoxide in methanol.
Q10: What cyclic ether is shown below?
O O
What is the product of this reaction?
O O
O O O
O O
I II III O O
   
   
1. I only 1. 18-crown-6
2. II only 2. 24-crown-8
3. III only 3. 24-crown-18
4. I and II 4. 18-crown-8
5. I, II and III 5. 5-crown-2