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17. Select the most acidic hydrogen in the compound shown below: A. HO C. H B....
17. Select the most acidic hydrogen in the compound shown below: A HO C. H ----...
17. Select the most acidic hydrogen in the compound shown below: A HO C. H ---- D. B. H H 18. Addition of methyl lithium to the enone below generates the product shown after treatment with acid and water. Select the key intermediate in the mechanism for the last step: OMe H2O Meli H2SO4 H2O Hato H2O OH H2O OMe OMe B. C. D. A
17. Select the most acidic hydrogen in the compound shown below: A. HO C D. B....
17. Select the most acidic hydrogen in the compound shown below: A. HO C D. B. 18. Addition of methyl lithium to the enone below generates the product shown after treatment with acid and water. Select the key intermediate in the mechanism for the last step: но Meli H. SO OME H2O HO Ho'o OH H20 OME OME 3. C D. A
Question 19 Which is the most acidic hydrogen in the compound shown? II IV H H...
Question 19 Which is the most acidic hydrogen in the compound shown? II IV H H H H H -H H T III V CA. V B. C. IV D. III E. 11 Question 20 How many signals would you expect to find in the TH NMR spectrum of CH 30CH 2 CH 2OCH 3? CA. 4 B. 2 C. 1 D.3 E. 5
10. Select the compound that can not be made using the malonic ester synthesis: O O...
10. Select the compound that can not be made using the malonic ester synthesis: O O OH MeO Оме OH Ph OH A. B. Ph C. D. 11. In general both the malonic ester and acetoacetate synthesis require the addition of dilute acid in order to generate the final product. Why? A. the alkoxy cation needs to be eliminated C. the ionized cation partitions to the aqueous layer B. the stabilized enolate adds a proton in the separatory funnel D....
Question 3 (a) Arange the following compounds in order of decreasing reactivity with nucleophiles (ie. most...
Question 3 (a) Arange the following compounds in order of decreasing reactivity with nucleophiles (ie. most reactive compound first). Explain your reasoning. (6 marks) C Me Me OMe OMe F C NMez Me Me Answer TWO parts from (i)-(iii) (7 marks each). (b) Give mechanisms for the following reactions and use them to explain the different (i) reaction outcomes. LIAIH он Me OMe Me LIAIH NMez Me NMeg Me (i) Give mechanisms for the following reactions and use them to...
2. I he compound below known as salicin is an old natural painkiller (from tree bark)....
2. I he compound below known as salicin is an old natural painkiller (from tree bark). In the presence of water and acid, salicin will be metabolized into a cyclic hemiacetal and the actual drug. Please provide the products of this reaction and a detailed mechanism, using curved arrows to indicate the movement of electrons. Hint: The ether oxygen on the benzene ring is somewhat more basic than the other ether oxygen. ?? ?? cat. H+ and H2O ?? ??...
(1)Phenylglyoxal. Phenylglyoxal is in equilibrium with its hydrate as shown: H + H2O HO OH (a)...
(1)Phenylglyoxal. Phenylglyoxal is in equilibrium with its hydrate as shown: H + H2O HO OH (a) Propose a mechanism for this reaction under acidic conditions. (b) Propose a mechanism for this reaction under basic conditions. The IR spectrum of the hydrate is shown below MICRONS NICOLET 20SX FT-IR 21 22 25 2.6 2.72.8 2.9 100 3 3.5 4.5 5.5 10 12 14 15 18 17 18 19 80 0.1 70 40 A 05 08 0.7 09 10 20 4000 3800...
with one another? no loan pais 1. For each compound shown below, number the illustrated protons...
with one another? no loan pais 1. For each compound shown below, number the illustrated protons according to their acidity: most acidic (1) to least acidic (3). (9 points) H H NH2 H OH HO F F OH O HS OH 13. Shown below is the formal structure of the amino acid methionine and its structure as it exists at physiological pH ( 7.3). In each case, the molecule itself is neutral; however at pH 7.3 there is an atom...
Acid Catalyzed Hydration-treatment of alkenes with water in the presence of acid catalyst leads to the...
Acid Catalyzed Hydration-treatment of alkenes with water in the presence of acid catalyst leads to the formation of alcohols. H2SO4/H2O > 150°C Mechanism Major Product Acid catalyzed dehydration goes through a carbocation intermediate. This means that the Markovnikov product is obtained when carbocation rearrangements do not occur. The need for excessively high temperatures makes this reaction of limited use in laboratory synthesis. Oxymercuration - Oxymercuration involves the addition of Hg to the alkene using mercury (II) acetate Hg(OAc) followed by...
30. Select the product for the reaction shown below: HO KOH A. B. C. 31. Provide...
30. Select the product for the reaction shown below: HO KOH A. B. C. 31. Provide the final product that results upon completion of the multi-step synthesis shown: NaoMe MeOH NaoMe H30+ / dil A Ph3P=CH2 ? OMe HCI Br Br NaOME O OH OH P+Ph3 Br A. Br C. D. B. CO2H
17. Select the most acidic hydrogen in the compound shown below: A HO C. H ---- D. B. H H 18. Addition of methyl lithium to the enone below generates the product shown after treatment with acid and water. Select the key intermediate in the mechanism for the last step: OMe H2O Meli H2SO4 H2O Hato H2O OH H2O OMe OMe B. C. D. A
17. Select the most acidic hydrogen in the compound shown below: A. HO C D. B. 18. Addition of methyl lithium to the enone below generates the product shown after treatment with acid and water. Select the key intermediate in the mechanism for the last step: но Meli H. SO OME H2O HO Ho'o OH H20 OME OME 3. C D. A
Question 19 Which is the most acidic hydrogen in the compound shown? II IV H H H H H -H H T III V CA. V B. C. IV D. III E. 11 Question 20 How many signals would you expect to find in the TH NMR spectrum of CH 30CH 2 CH 2OCH 3? CA. 4 B. 2 C. 1 D.3 E. 5
10. Select the compound that can not be made using the malonic ester synthesis: O O OH MeO Оме OH Ph OH A. B. Ph C. D. 11. In general both the malonic ester and acetoacetate synthesis require the addition of dilute acid in order to generate the final product. Why? A. the alkoxy cation needs to be eliminated C. the ionized cation partitions to the aqueous layer B. the stabilized enolate adds a proton in the separatory funnel D....
Question 3 (a) Arange the following compounds in order of decreasing reactivity with nucleophiles (ie. most reactive compound first). Explain your reasoning. (6 marks) C Me Me OMe OMe F C NMez Me Me Answer TWO parts from (i)-(iii) (7 marks each). (b) Give mechanisms for the following reactions and use them to explain the different (i) reaction outcomes. LIAIH он Me OMe Me LIAIH NMez Me NMeg Me (i) Give mechanisms for the following reactions and use them to...
2. I he compound below known as salicin is an old natural painkiller (from tree bark). In the presence of water and acid, salicin will be metabolized into a cyclic hemiacetal and the actual drug. Please provide the products of this reaction and a detailed mechanism, using curved arrows to indicate the movement of electrons. Hint: The ether oxygen on the benzene ring is somewhat more basic than the other ether oxygen. ?? ?? cat. H+ and H2O ?? ??...
(1)Phenylglyoxal. Phenylglyoxal is in equilibrium with its hydrate as shown: H + H2O HO OH (a) Propose a mechanism for this reaction under acidic conditions. (b) Propose a mechanism for this reaction under basic conditions. The IR spectrum of the hydrate is shown below MICRONS NICOLET 20SX FT-IR 21 22 25 2.6 2.72.8 2.9 100 3 3.5 4.5 5.5 10 12 14 15 18 17 18 19 80 0.1 70 40 A 05 08 0.7 09 10 20 4000 3800...
with one another? no loan pais 1. For each compound shown below, number the illustrated protons according to their acidity: most acidic (1) to least acidic (3). (9 points) H H NH2 H OH HO F F OH O HS OH 13. Shown below is the formal structure of the amino acid methionine and its structure as it exists at physiological pH ( 7.3). In each case, the molecule itself is neutral; however at pH 7.3 there is an atom...
Acid Catalyzed Hydration-treatment of alkenes with water in the presence of acid catalyst leads to the formation of alcohols. H2SO4/H2O > 150°C Mechanism Major Product Acid catalyzed dehydration goes through a carbocation intermediate. This means that the Markovnikov product is obtained when carbocation rearrangements do not occur. The need for excessively high temperatures makes this reaction of limited use in laboratory synthesis. Oxymercuration - Oxymercuration involves the addition of Hg to the alkene using mercury (II) acetate Hg(OAc) followed by...
30. Select the product for the reaction shown below: HO KOH A. B. C. 31. Provide the final product that results upon completion of the multi-step synthesis shown: NaoMe MeOH NaoMe H30+ / dil A Ph3P=CH2 ? OMe HCI Br Br NaOME O OH OH P+Ph3 Br A. Br C. D. B. CO2H
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