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- 9. Compound X, C40H67Br2F, reacts with excess H2/Pd to give a C40H73Br2F compound. How many rings are in X? How many double bonds are in X? Show your work. use ONLY reactions we have studied in class. Check your notes lides for preparations and reactions of relevant functionalChemistry CH3 CH3 CH3 O. HO. H3C CH3 H3C CH3 H3C CH3 (-)-menthol (-)-menthone (+)-neomenthol Hi, Could you please assist with providing the answers to question `1 a-d with an explaination to assist. 1.a) Label the stereogenic centers in (-)- menthol, (-)-menthone and (+)-neomenthol with an asterisk (*). b) Determine the configuration of each stereogenic center in (-)-menthol, (-)- menthone and (+)- neomenthol in terms of the R,S convention c) Draw each of (-)-menthol, (-)-menthone and (+)-neomenthol as two possible chair structures. Explain which is likely to be the more stable chair structure in each case. d) Explain whether you expect (-)-menthol or (+)-neomenthol to be thermodynamically more stable.The Claisen condensation can be used as one step in the synthesis of ketones, as illustrated by this reaction sequence. 1. EtO Na+ 2. HCI, H₂O Draw the structures of each of the major organic products. • You do not have to consider stereochemistry. • Do not include counter-ions, e.g., Na*, I, in your answer. (a) compound a O * Sn [F compound a ? NaOH, H₂O Heat compound b HCI, H₂O Heat compound c (C₁1H22O)
- Draw the organic product expected from the reaction. Include all hydrogen atoms. Note that K2Cr2O7K2Cr2O7 is present in excess. CH3CH2CH2OH+K2Cr2O7(aq) −→−−−H2SO4Study the reaction scheme shown below and answer all sections (i) – (v) relating to it. ? EC Na* ? E Br H F Reaction of alkyne D with a strong base gave an intermediate E, which reacted with compound F to give product G. Suggest a base that could be used in this reaction, and explain why the hydrogen that is removed is unusually acidic compared to other H atoms bonded to carbon. Propose a reagent and catalyst to accomplish the conversion of compound G into alkane H.Section B (continued) В4. Answer all parts (i-iv). Explain the reactions and observations shown in the schemes below: Scheme 1 of + КОMe Me- C4H8 Br not observed product Scheme 2 H2SO4 nok + MEOH Me HO Your answer should address the following points: i) Explain why the SN2 reaction in Scheme 1, leading to formation of the ether does not take place. Predict the structure of the product C4H8 arising from the reaction in Scheme 1 above. ii) iii) iv) Provide the mechanism accounting for the formation of the product C4H8. Provide a rational for the formation of the ether in Scheme 2.
- You must prepare the most stable possible alkene starting from the starting material given below and following an E2 elimination reaction. H Base Ö most stable alkene CH3 Ph Et Br PhDRAW THEM OUT 1. Predict the major organic product(s) for each of the following reactions. Be sure to clearly indicate the proper stereochemical relationships between groups (if appropriate), and write the word "racemic" next to any compound that is formed as a racemic mixture. a. i. j. H3C མིན་ CH3 excess NaOD excess D₂O1. Show the mechanism using curly arrows for the transformation of benzoic acid to benzoyl chloride using SOCI, as a reagent as shown below. Benzoic acid Benzoyl chloride 2. Carboxylic acid and their derivatives readily react with alcohols. (i) Name the reaction and give the generic name of the product of such a reaction. (ii) The reaction of salicylic acid with acetic anhydride is an example of such a reaction as in (i) above. Show the mechanism of the reaction. HO H* HO salicylic acid acetic anhydride acetyl salicylic acid (aspirin)
- Be sure to answer all parts. Complete the reactions to show the synthesis of the following product from the given starting material. Br OCH3 Br [1] BH3 [2] Н.О, НО- draw structure ... draw structure ... NaH CH3I + H2 OCH3 draw structure ... Select an appropriate compound for ?. H,SO4 O K* OC(CH3)3(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. H H;C-C-c CH, Br AIC13 NH, so, H,SO4 (ii) NH, Hfos CH;C1 AICI, (iii)3) The natural product Nuciferal was synthesized by the route summarized below. Supply the missing reagents in the blank spaces below and then attempt to answer questions A and B. OH BrMg A B CHO CHO Nuciferal A) Suggest a synthesis of the starting material A. You may use any organic with 3 carbons or less inorganic reagents necessary. B) Suggest reagents for step B. More than one reagent/step may be needed.