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CHE2245 Organic Chemistry II Assignment

This document outlines an assignment for the Organic Chemistry II module for Bachelor of Education students, detailing group work requirements and specific questions to be answered. The assignment consists of four questions focusing on stereochemistry, reaction mechanisms, and product structures, with a total of 10 marks available. It emphasizes academic integrity by stating that copied work will result in a zero score for both groups involved.
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100% found this document useful (1 vote)
73 views2 pages

CHE2245 Organic Chemistry II Assignment

This document outlines an assignment for the Organic Chemistry II module for Bachelor of Education students, detailing group work requirements and specific questions to be answered. The assignment consists of four questions focusing on stereochemistry, reaction mechanisms, and product structures, with a total of 10 marks available. It emphasizes academic integrity by stating that copied work will result in a zero score for both groups involved.
Copyright
© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
Available Formats
Download as PDF, TXT or read online on Scribd

1

COLLEGE OF EDUCATION

CHE2245 ASSIGNMENT I

DEPARTMENT: Mathematics, Science and Physical Education


PROGRAMME: Bachelor of Education
SUBJECT: Chemistry
ACADEMIC YEAR: 2025 SEMESTER: I YEAR OF STUDY: II (BCE, PCE and MCE)
MODULE CODE: CHE2245 MODULE TITLE: Organic Chemistry II
DATE: 14th – 21st April 2025 DURATION: 1week Total marks: 10

Instructions
i. This assignment must be done in groups of not more than 5 students each.
ii. If a group copies the whole assignment or part of it from another one, both groups receive zero
iii. Groups with odd no, will work on questions 1 and 4 while groups with even no, will work on
questions 2 and 4.

Question One (5 marks)


How could you prepare the following diastereoisomeric products from the same alkene?

OH OH
Ph ? Ph ? Ph
Ph Ph Ph
OH OH

Question Two (5 marks)


Draw out the structures of the products of the following reaction, showing all stereoisomers. Assign each
stereogenic center as R or S.
2

Cl
HO2C H2/Pt
CO2H
Cl

Question Three (5 marks)


Label the Re and Si faces in each of the following compounds and show your workings

a a a
O O CH2
(a) Et (a) Me (c) Et
H OMe Cl
b b b

Question four (5 marks)


Determine the stereochemistry of the major product expected from each of the following addition reactions.
Show the reaction mechanisms.

(R)-2-phenylpropanal with aqueous KCN

(S)-3,4,4-trimethyl-1-pentene with HBr

Good luck to you all !

Common questions

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Group assignments and collaboration promote active learning, where students engage with content through discussion and problem-solving, enhancing comprehension and retention. In complex fields like organic chemistry, collaboration allows exchange of diverse insights and methods, aiding in mastering difficult concepts and developing critical thinking. Such settings mirror real-world scientific collaborations, preparing students for future roles .

To prepare diastereoisomeric products from the same alkene, a syn or anti addition reaction can be utilized. Syn addition involves adding substituents on the same side of the double bond, while anti addition involves adding them on opposite sides. The choice of reagent and conditions influences which diastereomer forms. Diastereomers are important as they often exhibit different reactivity and physical properties, which can be exploited in synthesis and in studying molecular interactions .

Stereoisomeric mixtures can significantly impact a compound's physical properties and efficacy. Enantiomers often have distinct interactions with biological targets due to different spatial arrangements, affecting activity and side effects. In pharmaceuticals, pure enantiomers are often preferred to avoid adverse effects associated with the inactive or harmful isomers in a mixture. Achieving enantioselectivity in synthesis is therefore valuable for drug safety and effectiveness .

Preventing plagiarism is crucial in academia to maintain intellectual integrity, ensuring original contributions and respecting others' work. It fosters a fair learning environment and encourages critical thinking and creativity. Failing to prevent plagiarism undermines academic credibility and can lead to severe consequences such as academic penalties, damaged reputation, and loss of educational opportunities .

Stereochemical labeling involves explicitly marking stereocenters as R/S, Re/Si, or E/Z, providing detailed insight into the reaction pathways and intermediates formed. It helps identify stereoisomers formed and demonstrates how stereochemical information at reactant sites is transferred into products. This understanding aids in predicting product distributions, optimizing reaction conditions for selectivity, and designing stereo-controlled syntheses .

Understanding reaction mechanisms is vital for predicting outcomes of organic transformations as they provide a step-by-step breakdown of the process, revealing how reactants convert into products under specific conditions. They serve as a foundational tool in education, fostering deeper comprehension of chemistry through practical examples and aiding in developing problem-solving skills needed for complex chemical synthesis and analysis .

The addition of HBr to (S)-3,4,4-trimethyl-1-pentene involves the protonation of the alkene to form a carbocation, followed by a nucleophilic attack by the bromide ion. The stereochemistry of the (S)-configured starting material influences the preferred pathway and intermediacy of carbocations, affecting the stereochemistry of the final product through Markovnikov's rule, where the more substituted carbon forms the carbocation. The configuration can be determined from the stereochemical outcomes of these processes .

The reaction of (R)-2-phenylpropanal with aqueous KCN leads to the formation of a cyanohydrin, introducing a new chiral center. Depending on the facial selectivity of the nucleophile, the product can have diastereomeric or racemic mixtures. Such transformations are significant in synthetic chemistry, where controlling the stereochemistry of products is crucial for the synthesis of enantiomerically pure compounds, which is important for pharmaceuticals and natural products .

Assigning R or S configurations to stereogenic centers involves the Cahn-Ingold-Prelog priority rules. First, rank the substituents attached to the chiral center based on atomic number; the higher the atomic number, the higher the priority. Orient the molecule so the group of lowest priority is directed away from the viewer. If the sequence 1 → 2 → 3 is clockwise, the configuration is R; if counterclockwise, it is S. This impacts drawing reaction products by requiring clear depiction of stereochemistry, crucial for understanding reactions and properties of the molecules .

The Re or Si faces of a prochiral center are determined by assigning priorities to the groups around the center. When viewing the molecule's face, it is Re if the priority sequence 1 → 2 → 3 is clockwise and Si if it is counterclockwise. Identifying the faces is relevant when predicting stereochemical outcomes in reactions catalyzed by chiral environments, as many reactions occur preferentially on one face of a compound .

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