Write down the mechanism for the formation

Assignment Help Chemistry
Reference no: EM131593850

Answer the following questions:

1. Identify the substitution mechanism (SN1 or SN2) and write down the mechanism for the formation of 11 from compound 10 using curly arrows. Although compound 10 has two hydroxyl functional groups, only one was protected. Briefly explain this selectivity.

2. The 1H NMR spectral data for compound 9 is as follows:

1H NMR (500 MHz, CDCl3): δH 6.85 (d, J = 2.0 Hz, 1H), 6.82 (d, J = 8.5 Hz, 1H), 6.74 (dd, J = 8.5, 2.0 Hz, 1H), 6.60 (s, 1H), 5.55 (s, 1H), 4.00-3.94 (m, 4H), 3.89 (s, 3H), 2.06-2.00 (m, 4H), 1.90 (s, 3H), 1.70-1.65 (m, 4H), 1.20 (s, 1H) ppm

Assign the 1H NMR peaks to the corresponding hydrogen atom(s) shown in the molecule (Diagram 1, hydrogen environments a-n), giving reasons for their multiplicity, coupling constant and chemical shift values.

306_Figure1.jpg

Figure

3. The exact procedure for the formation of compound 8 is given below. Calculate the theoretical yield (g) of compound 8. Show the calculation steps involved in the calculation.

8-(Prop-1-en-2-yl)-1,4-dioxaspiro[4.5]decan-8-ol (8).

To a solution of isopropenylmagnesium bromide (0.5 M in THF, 1.8 L, 0.90 mol) was added a solution of 1,4 - dioxaspiro[4.5]decan- 8-one (100 g, 0.64 mol) in THF (200 mL) at a rate to maintain the reaction temperature below 5°C. After complete addition, the reaction mixture was stirred for 2 h. After this time, saturated ammonium chloride (200 mL) was added, and the mixture was extracted with ethyl acetate (2 L). The organic phase was washed with brine (300 mL, ×2), dried over MgSO4, and concentrated in vacuo to afford 8 as a brown solid (126 g, >99%).

Assessment: A take-home assignment on "The total Organic Synthesis Reactions and Mechanisms

Rationale

The questions will help the students practice their knowledge on chemical reactions in Organic Chemistry acquired during the pre-requisite unit, Organic Chemistry. It will provide the foundation to gain a more in-depth understanding of the mechanisms of some of the central reactions that form the basis of living processes, modern research, and contemporary industrial transformations.

Task

This is a take home, written assignment. The questions will be based on reactions covered during Levels 1 and 2 and may have been combined into a multi-step synthesis.

Students have to analyse the reaction procedure and reactants/products, and attempt questions related to the reaction and its mechanism. Student must also consider the stereo-chemical outcomes of each reaction.

The chemical structures and mechanism can be either hand drawn and/or using computer software.

Reference no: EM131593850

Questions Cloud

Insurance reduce intellectual property risk : How does cyber risk management and/ or insurance reduce intellectual property risk?
Judicial proceedings involved a determination of guilt : Which of the early forms of judicial proceedings involved a determination of guilt based on the ability of the accused to withstand placing his hand
What rate of return did she make per semiannual period : What rate of return did she make per semiannual period, and per year (nominal)?
True regarding currency options : Which of the following are true regarding currency options? The price of a European type call option must be equal to or_______
Write down the mechanism for the formation : Advanced Organic Chemistry - 300906 - write down the mechanism for the formation of 11 from compound 10 using curly arrows
Explain the law of increasing opportunity cost : (a) Explain the Law of Increasing Opportunity Cost. (b) What is the reason for the law?
Internal rate of return : You buy a new piece of equipment for $12, 539, and you receive a cash inflow of $2, What is the internal rate of return?
Market failure could worsen the situation : List five reasons why government's solution to a market failure could worsen the situation.
Writes all of the updated reservations in the list to a file : Writes all of the updated reservations in the list to a file. Print the itineraries of all of the reservations - Printed to the screen.

Reviews

len1593850

8/8/2017 5:08:01 AM

Rationale The questions will help the students practice their knowledge on chemical reactions in Organic Chemistry acquired during the pre-requisite unit, Organic Chemistry. It will provide the foundation to gain a more in-depth understanding of the mechanisms of some of the central reactions that form the basis of living processes, modern research, and contemporary industrial transformations.

len1593850

8/8/2017 5:07:35 AM

Credit Distinction High Distinction Sound description, using the appropriate terms and curly arrows to show electron movement in reaction mechanism and concepts to explain a phenomenon, and can correctly analyse the spectral data for most of the hydrogens in the product structure. Extensive description, using the appropriate terms and curly arrows to show electron movement in reaction mechanism and concepts to explain a phenomenon, and can correctly identify and explain the coupling and chemical shifts all of hydrogens in the product structure. Comprehensive description, using the appropriate terms and concepts to explain a phenomenon and the correct mechanism of the reaction, and can correctly assign all of the hydrogens in the product. Express concepts both qualitatively and quantitatively and provide extra relevant details and elaboration.

len1593850

8/8/2017 5:07:30 AM

Criteria Unsatisfactory Pass An ability to demonstrate knowledge and understanding of organic chemistry concepts, reaction mechanisms in organic synthesis and analysis of 1H NMR spectral data. Inadequate description without using relevant scientific terms or concepts to explain reaction mechanism or phenomenon. Also, no analysis of spectral data to assign hydrogen in the molecule. Adequate description only, using some terms and concepts to explain reaction mechanism and can only correctly identify some of the hydrogens in the structures.

Write a Review

Chemistry Questions & Answers

  Steps in the mechanism for the following reaction

Show all the steps in the mechanism for the following reaction, When benzene is mixed with deuterated sulfuric acid, deuterium is slowly incorporated onto the ring. Show the mechanism for this reaction and explain how this relates the sulfonation of ..

  Prior to placing piece of metal into the graduated cylinder

This assignment inhibits chemistry Laboratory Questions.

  Write the structures of the saytzeff elimination

Write the structures of the saytzeff elimination

  Calculate ph - chemistry questions

Chemistry Questions on Calculate P H

  How many mols of hydrogen can produce

how many mols of H 2 can produce

  Analysis of corrosion mechanisms

Analysis of corrosion mechanisms and preventative measures

  Chemical and pharmaceutical science

Write an equation for the formation of an acetal from reaction of excess methanol with benzaldehyde in the presence of an acid catalyst.

  Calculate the approximate sulphur

Calculate the approximate SO 2 mass emission in lb/day.

  What is the structure - stereochemistry

What is the structure (including functional groups)? Stereochemistry (racemic or single enantiomer)?

  Design a qualitative analysis scheme

Design a qualitative analysis scheme

  What will be the resultant pressure

What will be the resultant pressure when the stopcock is opened?

  The 1h nmr spectrum

Integrals for some of the resonances in the 1H NMR spectrum are higher than they should be due to the shear number of hydrogens in this compound

Free Assignment Quote

Assured A++ Grade

Get guaranteed satisfaction & time on delivery in every assignment order you paid with us! We ensure premium quality solution document along with free turntin report!

All rights reserved! Copyrights ©2019-2020 ExpertsMind IT Educational Pvt Ltd