aniline has a PRIMARY amine, the nitrogen has a lone pair, therefore it can attract easily the Hydrogen H+ ion, and become a base ( H+ acceptor)
for pyrole, the electrons are being used in the resonance structure of the ring, so they are not as free to attract H+ ions
therefore pKb is much lower
1. (10 Pts) Here are the pk, values for cyclohexylamine, pyridine, aniline and pyrrole. Explain the relative base strengths using piperidine as your standard for comparison. Amine Piperidine Pyridine Aniline Pyrrole 13.4 2. (5 Pts) Starting with benzene and any needed organic or inorganic reagents, synthesize 3. chloroaniline (meto-chloroaniline).
1. (8pts) The following molecule is pyrrole, an aromatic compound. A) Draw the structure with any/all orbitals including overlapping p orbitals. B) Briefly explain why this molecule is aromatic.
Q/ Pyrrole, pyridine and benzene are all aromatic compounds but their aromatic systems are built in different ways. Explain with structures (and molecular orbitals) the aromaticity of the three compounds. What common chemical character would indicate the difference and how?
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(7 pts) The acylation of pyrrole shown occurs faster than the acylation of benzene. a) Propose a mechanism for the reaction with pyrrole. b) State clearly the rate determining step in the reaction. c) With words and structures explain why pyrrole reacts more rapidly than benzene. d) With words and structures explain why pyrrole reacts at position 2 and not at position 1 or 3. 4. N AICly
2. Pyridine and pyrrole are both aromatic heterocyclic nitrogenous organic bases. However, they are not equally as strong as bases however. Pyridine is a much better base (pKb-8.75) than pyrrole (pKb 13.6. Provide an explanation for the difference in basicity between the two compounds. (12.5 points) Pyrrole Pyridine As a part of your answer, start by showing the mechanism of how each molecule accepts a proton.
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1. Both pyridine and pyrrole are nitrogen-containing aromiatio er yrole is unreactive (2 Paints lie c with HCLl, only pyridine forms the bydrochlorid explanation for this observed reactivity difference le salt, whereas pym pyridine pyrrole oice, of the following compounds below will undergo the fastest Sul reaction? Explain your (1 Point) choice. Cl Which one of the following compounds below will undergo the fastest Swl reaction? Explain your (1 Point) 3. choice. Br Br 4. Starting from A, propose a...