b) The imine shown below exhibits in vitro antibacterial activity toward M. tuberculosis H37Rv. It decomposes under acidic conditions in water to afford the products shown here. Propose a reasonable mechanism for this reaction. Include all mechanistic intermediates in their correct order, use arrows correctly to indicate bond making/breaking (i.e., movement of electrons, NOT atoms or charge symbols), and clearly show which atoms (if any) contain formal charges. H3O+ oc=00.00 OH OH CH=O OH H₂N. HO

b) The imine shown below exhibits in vitro antibacterial activity toward M. tuberculosis H37Rv. It decomposes under acidic conditions in water to afford the products shown here. Propose a reasonable mechanism for this reaction. Include all mechanistic intermediates in their correct order, use arrows correctly to indicate bond making/breaking (i.e., movement of electrons, NOT atoms or charge symbols), and clearly show which atoms (if any) contain formal charges. H3O+ oc=00.00 OH OH CH=O OH H₂N. HO

Organic Chemistry: A Guided Inquiry

2nd Edition

ISBN:9780618974122

Author:Andrei Straumanis

Publisher:Andrei Straumanis

Chapter13: Substitution

Section: Chapter Questions

Problem 4E

See similar textbooks

Similar questions

The phenyl group, C6H5, is known to be an ortho/para-directing group. (a) With that in mind, predict theproduct of the reaction shown here. (b) Justify why it is an ortho/para director by examining the ortho, meta,and para arenium ion intermediates that would beformed during the course of the reaction.
Compound D, shown below, reacts with hydrogen bromide by electrophilic addition. A mixture of two organic compounds, E and F, is formed. CH3 CH₂CH₂ CH3 H compound D HBr Mixture of organic compounds E and F (i) Name the the two organic compounds E and F and show their condensed formula. (ii) Briefly explain the mechanism of the reaction between compound D and hydrogen bromide to form either compound E or compound F. (You can list/state the main steps) (iii) Which compound, E or F is the major product?
The phenyl group, C,H5, is known to be an ortho/para-directing group. (a) With that in mind, predict the product of the reaction shown here. (b) Justify why it is an ortho/para director by drawing the ortho, meta, and para arenium ion intermediates that would be formed during the course of the reaction. Br2 FeBra
3 Draw the structure of the imine product that is created from the condensation of an amine and acetone. Sketch step-by-step mechanism for this reaction include any necessary arrows, intermediates, and formal charges.
Suggest a detailed mechanism for each of the reactions below. Explain why the originating products were formed.
Give a detailed explanation on the reaction of the compound and its mechanism and why did it happen.(see attached picture)
Many biochemical reactions utilize cationic imines (a Schiff base) as electron sinks. Illustrate your understanding of this concept by drawing the mechanism of basic imine formation between an aldehyde (RCHO) and an amine (RNH2). For full credit, you must show all electron flow (using the arrow convention).
Give a detailed explanation on the mechanism of the compound and why did it happen. (see attached picture)
An aromatic imine is formed when 3,5-dihydroxyphenol is treated with ethanenitrile (CH3CN) in HCI in the presence of a ZnCl, catalyst, as shown here. Propose ОН ОН CH3CN a mechanism for this reaction. HCI, ZnCl, HO HO. Но HN
During a recent synthesis of hispidospermidin, a fungal isolate and an inhibitor of phospholipase C, the investigators employed employed a novel Friedel-Crafts acylation on a nonaromatic system (J. Am. Chem. Soc. 1998, 120, 4039-4040). The following acid chloride was treated with a Lewis acid, affording a mixture of two products, 1 and 2. Propose a plausible mechanism for the formation of compounds 1 and 2. CI AICI 进一步农 COCI 2 Part 1 Incorrect. Which of the four mechanistic steps is happening? Add curved arrow(s) to draw the first step of the mechanism. Modify the given drawing of the products as needed to show the intermediate that is formed in this step. Use the +/- tools to add/remove charges. CH₂ H St Edit Drawing H₂C H CH₂ CI Q M ΟΣ
Acid (H+) catalyses the racemisation of compound C and base catalyses the racemisation of compound D. (a) Explain the term racemisation and illustrate with a diagram for each molecule C and D (draw some mirror images!). (b) Propose mechanisms for both of these racemisation processes. [Hints: start by looking at your diagram from part a to see what you have to accomplish overall. Now think about how compound C will react with H and what a base would do to compound D? Focus on the functional groups there is no chemical 'magic' happening here - the reactions are very simple, but both require more than one step]. OH D -
G. (a) Identify the acid and base in each of the following reaction. (b) Show the mechanism by using arrows. (c) For each reaction, what acid-base concept (or definition) is applicable in classifying them? Explain why. Label the acid and base below the structure. Acid-base concept. Explanation Draw arrow (You may copy/paste the reaction in paint or powerpoint to be able to draw the arrow. You may also draw the arrow manually.) 1. :0: II CHIC-H + CH30: :ö: CH3C-H :OCH3 H 2. :0: :0: + H CH3-C-CH3 + CH3-C-CH3 H-