(9) An element which is used to observe the physical property brittlness
1 answer:
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Answer:
Here's what I get
Explanation:
You may have done a Williamson synthesis of guaifenesin by reacting guaiacol with 3-chloropropane-1,2-diol.
A. Mechanism
Step 1
NaOH converts guaiacol into a phenoxide ion.
Step 2
The phenoxide acts as the nucleophile in an SN2 reaction to displace the Cl from the alkyl halide.
B. Improve the yield
You probably carried out the reaction in ethanol solution — a polar protic solvent.
You might try doing the reaction in a polar aprotic solvent— perhaps DMSO.
A polar aprotic solvent does not hydrogen bond to nucleophiles, so they become stronger.
C. Another method of ether synthesis —dehydration of alcohols
Sulfuric acid catalyzes the conversion of primary alcohols to ethers.
This is also a nucleophilic displacement reaction.
Protonation of the OH converts it into a better leaving group.
Attack by a second molecule of alcohol forms the protonated ether.
A molecule of water then removes the proton.
Answer:
Here's what I get
Explanation:
(a) Intermediates
The three structures below represent one contributor to the resonance-stabilized intermediate, in which the lone pair electrons on the heteroatom are participating (the + charge on the heteroatoms do not show up very well).
(b) Relative Stabilities
The relative stabilities decrease in the order shown.
N is more basic than O, so NH₂ is the best electron donating group (EDG) and will best stabilize the positive charge in the ring. However, the lone pair electrons on the N in acetanilide are also involved in resonance with the carbonyl group, so they are not as available for stabilization of the ring.
(c) Relative reactivities
The relative reactivities would be
C₆H₅-NH₂ > C₆H₅-OCH₃ > C₆H₅-NHCOCH₃
