Retrosynthesis Assignment | Get Paper Help

This problem solving task needs to be solved to a third year university level, meeting all the requirements of the taskCVB301 Problem Solving Task 2020
This item is worth 30% of the assessment in CVB301.
General Instructions
• You must work independently of your colleagues (see “Academic Integrity Kit” on Blackboard) . Many of the problems posed can be solved multiple different ways, so when the problems are worked on in groups it is very obvious to the assessors!
• You have all the resources provided for the unit, plus any other sources you care to use. I will not be discussing it with you, except to clarify any questions of procedure or to remedy any errors in the documentation.
• This assignment is due through Blackboard by Friday 29th May. The time for submission is not negotiable except under extenuating circumstances that fit within the Unit Policy on assessment as provided in the Unit Information. The time limits are explained in that document – you can contact me by email (j.blinco@qut.edu.au) or phone (31384207).
• The assessment will be conducted using the Criterion Matrix provided on the Blackboard site. Part 1a, Part 1b and Part 2 are all equally weighted (10% each).
2
PART ONE
Objectives
1. To allow you to contemplate synthesis problems in a realistic problem-solving situation – i.e., not under the artificial time pressures of a “normal” exam [you should be able to get some solution, even if it is not the ‘intended’ answer, i.e., the one I used when developing the question].
2. To allow you to revise and demonstrate previously and newly acquired knowledge in Organic Chemistry by applying that knowledge to the solutions of the problems.
3. To allow you to demonstrate the principles of synthesis design and selectivity, especially as related to reagents and reaction conditions.
Instructions
1. Show by means of retrosynthesis, synthetic schemes and explanatory notes, how you would carry out the following two syntheses. You may use any other reagents and starting materials you choose, as long as the nominated substance(s) is/are used.
2. Remember the principles of selectivity and control, and note any regio- or stereochemical problems that might arise.
3. Provide brief notes and comments on each step, indicating any special reaction conditions, catalysts and solvents normally associated with the transformations you propose. Reaction mechanisms are not required in this Part.
(a)
CHOfrom acrolein
(b)
Ofrom acetoacetic ester
3
PART TWO
Objectives
1. To offer an opportunity for some creative original thought in organic chemistry.
2. To reinforce the principles of selectivity in organic synthesis.
3. To allow you to demonstrate previously and newly acquired knowledge in Organic Chemistry synthesis and reaction mechanisms by the solution of an individual problem.
Instructions
The Task:
1. You have been assigned the following compound: cyclopentanone
**PLEASE BE SURE YOU KNOW THE STRUCTURE OF YOUR STARTING MATERIAL BEFORE COMMENCING – the name may be a trivial one.**
2. Your compound is a “readily available starting material”.
3. DEVISE A SEVEN-STEP SYNTHESIS STARTING FROM THIS COMPOUND, i.e., you create your own target molecule. You may use any chemically reasonable reactions and any other reagents as necessary, but there must be two or more C–C bond forming reactions included.
Requirements:
1. (a) Present the synthesis as a reaction scheme, giving all reagents and any special reaction conditions required. (b) For each step, give mechanisms, notes and comments (especially if there may be selectivity problems).
2. Trivial procedures normally considered an integral part of a reaction step, e.g., the hydrolytic work-up of a Grignard reaction, do not count as a separate step.
3. Circular or trivial schemes will not be well received! For example, all the carbon skeleton of the starting material should appear in the final product of your scheme (this would not include the ethyl groups of an ethyl ester or diethyl acetal, etc.).
4. Bear in mind the principles of selectivity, activation and protection.
5. Feel free to use reactions not covered specifically in this Semester and earlier courses, but give brief references where this is done.
6. Hint: don’t try to be too complex as you may cause yourself regio- or stereoselectivity problems.