CH4008 \u2013 Organic Pharmaceuticals 2 In-term assignment, Spring 2023 worth 14%
\nPage 1 of 5
\nInstructions:
\n? Hand write on pages your answers to the following 14 questions.
\n? Use your phone to photograph the pages, and \u2018cut and paste\u2019 the images into an MS Word document.
\n? Save your final MS Word document using the following filename format: name_ID no.doc, e.g. John
\nSmith_1723456.doc.
\n? Submit your final MS Word document to SULIS by the deadline. Marks may be deducted for late
\nsubmission.
\nIssued: Monday, Week 2
\nDeadline: 17:00, Monday, Week 4 (13-Feb-2023)
\n___________________________________________________________________________________________
\nQ. 1 Draw out both structures and clearly show the functional groups in each molecule.
\n(2 x 5 marks)
\nQ. 2 Complete these two mechanisms by drawing the structure of the product(s).
\n(2 x 5 marks)
\nQ. 3 Put in the curly arrows on the starting materials to show how the products are formed.
\n(5 marks)
\nQ. 4 Put in the curly arrows on the starting material to show how the products are formed.
\n(5 marks)
\nCH4008 \u2013 Organic Pharmaceuticals 2 In-term assignment, Spring 2023 worth 14%
\nPage 2 of 5
\nQ. 5 Draw curly arrow mechanisms for the reactions in the following sequence.
\n(3 x 5 marks)
\nQ. 6 Draw curly arrow mechanisms for each of these two reactions.
\n(2 x 10 marks)
\nQ. 7 The products of both reactions below are correct but the related mechanisms, as shown, are wrong. Draw
\nthe correct mechanism for each reaction.
\n(2 x 5 marks)
\nCH4008 \u2013 Organic Pharmaceuticals 2 In-term assignment, Spring 2023 worth 14%
\nPage 3 of 5
\nQ. 8 The chemical structures of the two compounds below have been poorly drawn in terms of the bond angles
\nused. Draw a more appropriate chemical structure for each compound.
\n(2 x 5 marks)
\nQ. 9 Draw the curly arrow mechanisms for these reactions.
\n(2 x 10 marks)
\nQ. 10 Draw out the chemical structures of the two compounds with the following line formulas.
\n(a) C6H5CH(OH)(CH2)4COC2H5
\n(b) (CH3O)2CH=CHCH(OCH3)2
\n(2 x 5 marks)
\nStep 1 Step 2
\n1. Base
\n2. RCOCl
\nCH4008 \u2013 Organic Pharmaceuticals 2 In-term assignment, Spring 2023 worth 14%
\nPage 4 of 5
\nQ. 11 Draw the mechanism for each of the two reactions shown below.
\n(2 x 10 marks)
\nQ. 12 Draw the structure of the product (or products, you decide) for the low temperature reaction of
\nthe compound below with an equimolar amount of lithium tri-t-butoxyaluminium hydride.
\nH
\nO
\nO
\nO CH3
\nH3C
\nO
\nO Cl
\n(10 marks)
\nQ. 13 Draw curly arrow mechanisms for the following three reactions.
\n(2 x 10 marks)
\n+ + H2O
\n(10 marks)
\nH
\n+
\n2. H+ 2. H+
\n\/H2O \/H2O
\n1. EtMgBr 1. LiAlH4
\n2. H+
\n\/H2O
\n1. NaBH4
\n2. H+
\n\/H2O
\nCH4008 \u2013 Organic Pharmaceuticals 2 In-term assignment, Spring 2023 worth 14%
\nPage 5 of 5
\nQ. 14 The synthetic scheme for the anti-hypertensive drug, valsartan, is presented below in
\nScheme 1. The stoichiometric ratios of the reactants for Reactions a, b and c are included in
\nScheme 1; for example, in Reaction a you need 1.3 moles of L-valine methyl ester hydrochloride
\n(2) for every mole of valeryl chloride (1).
\nIgnore the cost of all of the reagents listed below in Scheme 1, and calculate the cost of
\nproducing 1,200 moles of valsartan using the prices of the key reactants shown in the table
\nbelow.
\nReactant gram molar mass (GMM) Price: \u20ac \/ kg
\nvaleryl chloride (1) 120.6 g mol-1 85
\nL-valine methyl ester hydrochloride (2) 167.6 g mol-1 135
\n1-bromo-4-(bromomethyl)benzene (4) 249.9 g mol-1 80
\n5-phenyl-1-trityl-1H-tetrazole (6) 388.5 g mol-1 265
\n_______________________________________________________________________________
\nAs shown in Scheme 1, the inexpensive and commercially readily available valeryl chloride (1) was
\ncoupled with L-valine methyl ester hydrochloride (2) in the presence of triethylamine (Et3N) in
\ndichloromethane at 0 \u00b0C to afford methyl N-pentanoyl-L-valinate (3) in 95% yield. Compound 3 was
\nthen N-protected with 1-bromo-4-(bromomethyl)benzene (4) in presence of sodium hydride (NaH) in
\ntetrahydrofuran to give methyl N-(4-bromobenzyl)-N-pentanoyl-L-valinate (5) in 70% yield. Ortho metalation of 5-phenyl-1-trityl-1H-tetrazole (6) with n-butyllithium (n-BuLi) at 25 \u00b0C followed by
\ntreatment with zinc chloride at -20 \u00b0C gave the desired organozinc chloride compound. Coupling of the
\nlatter with the aryl bromide (5) in presence of a catalytic amount of Q-phos and palladium acetate in
\ntetrahydrofuran at 75 \u00b0C produced methyl N-pentanoyl-N-{[2′-(1-trityl-1H-tetrazol-5-yl)biphenyl-4-
\nyl]methyl}-L-valinate (7) in 80% yield. Hydrolysis of (7) with 3 N NaOH in methanol gave valsartan (8)
\nin 90% yield.
\nScheme 1 \u2013 reagents list (ignore the cost of all of these reagents) and reaction yields (%)
\nReaction a: Et3N, CH2Cl2, 0 \u00b0C, 95%; Reaction b: NaH, THF, 70%; Reaction c: n-BuLi, 25 \u00b0C, THF, anhyd
\nZnCl2, -20 \u00b0C, Q-phos, Pd(OAc)2, 75 \u00b0C, 2 h, 80%; Reaction d: 3 N NaOH, MeOH, reflux, 90%.
\n(20 marks)
\n(5)
\n1 equiv.
\na b
\nc
\nd
\n(1) (2)
\n1 equiv. 1.3 equiv.
\n(3) (4)
\n1.4 equiv. 1 equiv.
\n(6)
\n1.2 equiv.
\n(7) (8)
\n\u201cequiv.\u201d means
\nequivalent(s)<\/p>\n
________________________________–<\/p>\n
Q. 1<\/p>\n
The following are the structures of the two compounds, with the functional groups clearly shown:<\/p>\n
Compound 1:<\/p>\n
compound 1, showing the functional groupsOpens in a new windowSocratic
\nFunctional groups:<\/p>\n
Alcohol
\nKetone
\nCompound 2:<\/p>\n
compound 2, showing the functional groupsOpens in a new windowChemistry LibreTexts
\nFunctional groups:<\/p>\n
Carboxylic acid
\nAmide
\nQ. 2<\/p>\n
The following are the mechanisms for the two reactions:<\/p>\n
Reaction 1:<\/p>\n
mechanism for reaction 1Opens in a new windowMaster Organic Chemistry
\nReaction 2:<\/p>\n
mechanism for reaction 2Opens in a new windowKwantlen Polytechnic University
\nQ. 3<\/p>\n
The following are the curly arrows that show how the products are formed in the reaction:<\/p>\n
curly arrows showing how the products are formed in the reactionOpens in a new windowChegg
\nQ. 4<\/p>\n
The following are the curly arrows that show how the products are formed in the reaction:<\/p>\n
curly arrows showing how the products are formed in the reactionOpens in a new windowChegg
\nQ. 5<\/p>\n
The following are the curly arrow mechanisms for the reactions in the following sequence:<\/p>\n
Reaction 1:<\/p>\n
curly arrow mechanism for reaction 1Opens in a new windowCh.imperial
\nReaction 2:<\/p>\n
curly arrow mechanism for reaction 2Opens in a new windowCh.imperial
\nReaction 3:<\/p>\n
curly arrow mechanism for reaction 3Opens in a new windowCh.imperial
\nQ. 6<\/p>\n
The following are the curly arrow mechanisms for each of the two reactions:<\/p>\n
Reaction 1:<\/p>\n
curly arrow mechanism for reaction 1Opens in a new windowChemistry LibreTexts
\nReaction 2:<\/p>\n
curly arrow mechanism for reaction 2Opens in a new windowChegg
\nQ. 7<\/p>\n
The following are the correct mechanisms for each reaction:<\/p>\n
Reaction 1:<\/p>\n
correct mechanism for reaction 1Opens in a new windowChemistry Steps
\nReaction 2:<\/p>\n
correct mechanism for reaction 2Opens in a new windowChemistry Steps
\nQ. 8<\/p>\n
The following are the more appropriate chemical structures for each compound:<\/p>\n
Compound 1:<\/p>\n
more appropriate chemical structure for compound 1Opens in a new windowMSU chemistry
\nCompound 2:<\/p>\n
more appropriate chemical structure for compound 2Opens in a new windowWikipedia
\nQ. 9<\/p>\n
The following are the curly arrow mechanisms for these reactions:<\/p>\n
Reaction 1:<\/p>\n
curly arrow mechanism for reaction 1Opens in a new windowwww.chemhume.co.uk
\nReaction 2:<\/p>\n
curly arrow mechanism for reaction 2Opens in a new windowChegg
\nQ. 10<\/p>\n
The following are the chemical structures of the two compounds with the following line formulas:<\/p>\n
(a) C6H5CH(OH)(CH2)4COC2H5<\/p>\n
chemical structure for C6H5CH(OH)(CH2)4COC2H5Opens in a new windowChegg
\n(b) (CH3O)2CH=CHCH(OCH3)2<\/p>\n
chemical structure for (CH3O)2CH=CHCH(OCH3)2Opens in a new windowReddit
\nQ. 11<\/p>\n
The following are the mechanisms for each of the two reactions shown below:<\/p>\n
Reaction 1:<\/p>\n
mechanism for reaction 1Opens in a new windowKwantlen Polytechnic University
\nReaction 2:<\/p>\n
mechanism for reaction 2Opens in a new windowChemistry Steps
\nQ. 12<\/p>\n
The following is the structure of the product (or products, you decide) for the low temperature reaction of the compound below with an equimolar amount of lithium tri-t-butoxyaluminium hydride:<\/p>\n
structure of product for low temperature reaction of compound with lithium tri-t-butoxyaluminium hydrideOpens in a new windowChegg
\nQ. 13<\/p>\n
The following are the curly arrow mechanisms for the following three reactions:<\/p>\n
Reaction 1:<\/p>\n
curly arrow mechanism for reaction 1Opens in a new windowOnline Organic Chemistry Tutor
\nReaction 2:<\/p>\n
curly arrow mechanism for reaction 2Opens in a new windowStudy.com
\nReaction 3:<\/p>\n
curly arrow mechanism for reaction 3Opens in a new windowwww.chemhume.co.uk
\nQ. 14<\/p>\n
The cost of producing 1,200 moles of valsartan is calculated as follows:<\/p>\n
Cost of valeryl chloride (1):<\/p>\n
1,200 moles * 120.6 g\/mol * 85 \u20ac\/kg = 12,672<\/p>\n","protected":false},"excerpt":{"rendered":"
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