1. Answer ALL parts of this question. OH IN Ph Ph 1 Figure Q1 (a) Provide a two-step retrosynthetic analysis of the fenpiprane analogue 1 (Figure Q1). In your answer account for all synthons and synthetic equivalents, and label the two retrosynthetic arrows, indicting the type of disconnection taking place. (b) Draw the two reaction schemes with viable reagents required for the synthesis of 1. (c) Give plausible curly arrow mechanisms for both reactions in the sequence drawn in part (b) required to make 1.

1. Answer ALL parts of this question. OH IN Ph Ph 1 Figure Q1 (a) Provide a two-step retrosynthetic analysis of the fenpiprane analogue 1 (Figure Q1). In your answer account for all synthons and synthetic equivalents, and label the two retrosynthetic arrows, indicting the type of disconnection taking place. (b) Draw the two reaction schemes with viable reagents required for the synthesis of 1. (c) Give plausible curly arrow mechanisms for both reactions in the sequence drawn in part (b) required to make 1.

Chemistry

10th Edition

ISBN:9781305957404

Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Chapter1: Chemical Foundations

Section: Chapter Questions

Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...

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Q6. Enolates and their surrogates. (a) Rank the acidity of the following compounds from LEAST (left) to MOST (right) by entering the corresponding numbers in the boxes provided. 1 4 2 NaNH, CO₂Me 5 3 CHO (b) Complete the following reaction products by adding the correct bonds, atoms and charges, as necessary.
Q1. Provide short definitions (2 sentences) for the following and bear in mind often a diagram could be used. (a) What is meant by the term retrosynthetic analysis? (b) What is a disconnection? (c) What is a synthon? (d) What is a synthetic equivalent? (e) What is meant by FGI? (f) What is meant by FGA?
Each of the following is a set of directions for carrying out a reaction or sequence of reactions. Rewrite each set ofdirections in the form of a synthesis.(a) To 2-ethylcyclohexanone, add lithium diisopropylamide, and when that reaction is complete, add bromoethane toyield 2,6-diethylcyclohexanone.(b) Add molecular bromine to 2,2-dimethylcyclohexanone in the presence of acetic acid to yield 6-bromo-2,2-dimethylcyclohexanone. To the resulting mixture, add sodium cyanide to yield 6-cyano-2,2-dimethyl-cyclohexanone.(c) Treat pent-4-ynoic acid with diazomethane to produce methyl pent-4-ynoate. Next, add sodium hydride, followed by(bromomethyl)benzene, to yield methyl 6-phenylhex-4-ynoate.
7. Answer ALL parts of this question. (a) Answer BOTH parts of this question Reaction of the carboxylic acid below (Scheme Q7(a)) with bromine in the presence of dibenzoylperoxide gives rise to an unstable compound A (CSH&BR2O2) that gives a stable compound B on treatment with a base. The stable compound has IR peaks at 1735 and 1645 cm and NMR peaks at &H (ppm) 6.18 (1H, s), 5.00 (2H, s) and 4.18 (2H, s). Br. Base (PhCO, Scheme Q7(a) (1) What is the structure of the unstable compound A? (i) Show the mechanisms for the two steps in the reaction (b) Answer BOTH parts of this question Tetraphenylporhyrin (TPP) is a singlet sensitiser that reacts with oxygen and can engage in pericyclic reactions (Scheme Q7(b). OH O. TPP hv Scheme Q7(b) (i) Explain the difference between a singlet and a triplet state. (ii) Show the mechanism for the reaction shown in Scheme 07(b) (ii) Consider the below reaction (figure Q7(c)), Show the structure of the product (C) anc the mechanism Scheme Q7 (b)
Q16. What are the necessary reagents to perform the following synthesis? Choose the answer from the options below. DG (0) CH3MgBr/ether (1) NaBH4, (2) H3O*(aq) c) H₂, Pt d) (1) CH3MgBr/ether, (2) H3O*(aq) (ii) dilute HCl(aq) conc. H₂SO4(aq) conc. H₂SO4(aq) conc. H₂SO4(aq)
Provide the reagents for the short syntheses (about 3-4 steps).
A student was given from the list of the conmpounds below A, B and D blindly and asked to identify them all. He treated each of them with Brady's reagent (2,4-ditrophenylhydrazine) and isolated a bright yellow compound for one of them, but the other two gave false negatives. The student reasoned that the false negatives may be due to sterics and, on further thinking, it dawned on him that he might be able to rule out one of the false negatives with the haloform test. What compound did he find compatible with the haloform test? That compound did indeed give a false negative in the Brady test. Which of the other two was positive in the Brady test? A = haloform B = Brady A = haloform D = Brady B = haloform A = Brady B = haloform D = Brady D = haloform A = Brady D = haloform B = Brady
(a) Tsomane and Nyiko were given a task of synthesising methylenecyclohexane 2. After a brief discussion with each other, Tsomane proposed Method A to synthesise 2 from cyclohexanone 1 while Nyiko proposed Method B that started from hydroxymethylcyclohexane 3. Each student believed that their proposed method is better than the other. (Scheme below) Ph THF A Ph Ph B H₂SO4 100 °C 3 OH (iii) In analysing both these methods, are there other possible alkene products other than methylenecyclohexane 2? Use mechanistic details to support your answer.
Consider the transformation shown in Scheme 1 and answer ALL parts of the question. O (1) (a) Identify reagent X. H i. Reagent X, Et₂O ii. H*, H₂O Scheme 1 (b) Name compounds (I) and (II). OH (11) (c) Provide a curly arrow mechanism for the transformation in Scheme 1. (d) Why is diethyl ether a good solvent for use with reagent X? (e) Why is it important to use reagent X under anhydrous conditions?
(b) The activating and deactivating groups could affect the position(s) of the next incoming group(s) to the benzene ring. Based on the structure below, analyze and explain the group(s) on the benzene ring is activating or deactivating group. Then, identify the product(s) formed from the following reactions. NH, CC, CH;CH,COCI AICI, (i) NH, HNO, H,SO, (ii) H Br AICI, (iii) Page 3 of 4
(C) ntify the reagen out) in Scheme 6. (D) Another repeating transformation is the reductive amination that shows up in the Schemes 3, 5 and 6. This takes Ar-NH₂ to Ar-N(CH3)2 with NaBH4/HCHO (formaldedyde). This provides the “rear" dipole that drives the nanocar. Show the mechanism for converting Ar-NH2 → Ar-N(CH3)2 with two formaldehyde molecules and NaBH4. You will need to review your notes from lab5 in chem210L that used NaBH4.
4. (A) A medicinal chemist wished to make a series of aromatic molecules bearing a ketone and thioether group with ortho, meta, or para relationships. To achieve this, they propose using nucleophilic aromatic substitution treating the corresponding ortho, meta, and para aryl chlorides with sodium ethanethiolate (NaSEt). Predict which of these reactions will likely work and which will likely fail. Provide a mechanistic explanation why. SET O NasEt EtS glagol Glal ol heat EtS target molecules EtS (B) Would the analogous reactions using EtMgBr instead of NaSEt be more or less likely to work? Explain why or why not. لمسلم EtMgBr