An important route to synthesize unsymmetrical ether is Williamson ether synthesis. This reaction is an example of Nucleophilic substitution reaction (SN2 Reaction). It involves the reaction generally between alkyl halide and alkoxide ion. 1° Alkyl halide and 1° Alkoxide ion give the best yield of ether during this reaction.
O CH3
1. Best method to prepare is the combination of:
KOH CH3I Cl OH Na (C) MeOH (A) Na CH3I OH
(B) (D) Both (A) and (B)
NaH Me-I H OH
2. Identify the final product:
H OMe MeO H
(A) (B)
Page No. 1 H OMe (D) None of these (C)
3. Identify product: EtO- + Ph-CH2-Cl
(A) Ph O (C) H2C CH2
O (B) Ph O (D) Ph
4. Which of the following is an appropriate set of reactants for the
preparation of 1-Methoxy-4-nitrobenzene? Br ONa
+ CH3Br
+ CH3ONa (C) O2N
(A) ONa ONa
+ EtONa + CH3Br (D) O2N
(B) NO2
5. Suitable combination of reactant to prepare:
O Ph
Br ONa (A) Ph + ONa
Br
(B) Ph +
Page No. 2 – O Br (C) Ph +
– O Br (D) Ph +
CH3
H OK EtBr Product H CH3
6. Et Correct stereochemical relationship between reactant and product will be: (A) Enantiomer (C) Structural Isomer (B) Diastereomer (D) None of these
7. Which of the following can’t be prepared by Williamson ether synthesis?
O (A) (B) O
(C)
(D)
8. Incorrect statement regarding the Williamson ether synthesis is:
(A) Less hindered halide is used in this reaction. (B) Less hindered alkoxide ion is used in this reaction. (C) Mechanism of reaction will be SN2. (D) More hindered halide is used in this reaction.
9. Which of the following ether is not synthesized by Williamson ether
synthesis?
Page No. 3 O CH3 O
(A) (C)
O O
(B) (D)
10. RO-Na+ + R’-L ROR’ + Na+L-
Rate of reaction will be maximum when L is: (A) CF3SO3- (Triflate Ion)
H3C SO 2- (p-Toluene sulphonate)
(B) (C) Br- (D) I-
11. Identify the products:
KH TsCl A OH B
12. The best combination for the preparation of ether by Williamson’s
synthesis are: (A) (CH3)3CBr and CH3Ona (C) CH3Br and (CH3)3CONa (B) (CH3)3CBr and CH3OH (D) CH3Br and (CH3)3COH
Page No. 4 ANSWERS
1. B 2. A 3. B 4. C 5. D 6. D 7. C 8. D 9. CD 10. A
