Synthesis of p-Bromoaniline The student observes a melting point of 110-113 C for the acetanilide. The literature melting point is 114 C. Which conclusion can he draw from these observations? (Check all that apply) a) The compound has 98 % purity. b) The sample is still wet. c) The solid is impure. d) The isolated compound in the target compound. Experiment 6: Synthesis of p-BromoanilineIntroductionSince the amino group of aniline is a strong activator of the aromatic ring, direct bromination isimpractical because it leads to several products (equation 1) that are difficult to separate. To makethe desired product, the amino group needs to be protected as the acetamide, which also maintainsthe direction of the incoming electrophile into ortho and para position. It slows down the rate ofreaction and introduces steric hindrance for the ortho positions (equation 2). Both factors lead toan increased selectivity for the desired para product (equation 3). The acetamide can be hydrolyzedback to the amine (equation 4). This strategy of protection and deprotection is a very importanttool in organic chemistry, especially in multi-step synthesis. In this experiment, p-bromoanilinewas synthesized in three steps starting from aniline.Equation 1:NH2NH2BrBrzplus mono-and disubstitution productsEquation 2:NH3NHEquation 3:NHBrzEquation 4:NHNH2Acid hydrolysisBrBr

Now a days different spectroscopic techniques have been introduced to check the purity of a…

Synthesis of p-Bromoaniline The student observes a melting point of 110-113 C for the acetanilide. The literature melting point is 114 C. Which conclusion can he draw from these observations? (Check all that apply) a) The compound has 98 % purity. b) The sample is still wet. c) The solid is impure. d) The isolated compound in the target compound.

Synthesis of p-Bromoaniline The student observes a melting point of 110-113 C for the acetanilide. The literature melting point is 114 C. Which conclusion can he draw from these observations? (Check all that apply) a) The compound has 98 % purity. b) The sample is still wet. c) The solid is impure. d) The isolated compound in the target compound.

Organic Chemistry: A Guided Inquiry

2nd Edition

ISBN:9780618974122

Author:Andrei Straumanis

Publisher:Andrei Straumanis

Chapter19: Eas: Electrophilic Aromatic Substitution

Section: Chapter Questions

Problem 21E

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