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7. The follov ng reaction sequence a decarboxylat on reaction similar to th gmatropic ester synthes...
The Malonic Acid synthesis is similar to the Acetoacetic Ester synthesis It uses diethyl malonate as...
The Malonic Acid synthesis is similar to the Acetoacetic Ester synthesis It uses diethyl malonate as the main starting material Draw the structure of diethyl malonate (malonic ester) Diethyl malonate can be hydrolyzed back to malonic acid and if heat is applied after the hydrolysis, will decarboxylate. Draw the mechanism for this transformation starting with malonic acid. Indicate the new C-C bonds in each molecule and then provide the organohalides which were used to synthesize each compound using the malonic...
12) Provide the structure of the major organic product in the reaction below. РОС Is 13)...
12) Provide the structure of the major organic product in the reaction below. РОС Is 13) Chromic acid oxidations are believed to proceed through a chromate ester intermediate. In its conversion to the intermediate aldehyde. Answer n-1-ol, provide the structure of this ester and give the mechanism for 14) What series of synthetic steps could be used to carry out the transformation shown below? Answer (three steps): 2. 3. 15) Reaction of ethylmagnesium bromide with which of the following compounds...
Claisen Condensations Claisen condensations involve the enolate anion of an ester which acts as a nucleophile...
Claisen Condensations Claisen condensations involve the enolate anion of an ester which acts as a nucleophile attacking another molecule of ester. The resulting product of this reaction is a Beta-ketoester. Draw the enolate anion which serves as the nucleophile in the reaction above. Draw the resonance structure of this enolate. Look at the mechanism of this reaction in your textbook (7^th edition), pages 773-774. What type of reaction does this resemble, S_N1,S_N2, E1, or E2? Ethanol is one of the...
Show the product of reaction of the indicated ester with LDA, followed by butyl iodide. CHÚCH...
Show the product of reaction of the indicated ester with LDA,
followed by butyl iodide.
CHÚCH 0 1. Provide a correct name for the indicated ester. 2. How many signals would we expect to see in the 13C NMR spectrum? 3. Show the combination of reagents required to synthesize the indicated structure using a Fischer esterification reaction. 4. a. The indicated ester is submitted to Claisen condensation conditions, using the appropriate alkoxide base and a second acidification step. The product...
6. (4 pts.) Draw the two resonance structures of the enolate formed from the following reaction: 7. (4 pts) Draw th...
6. (4 pts.) Draw the two resonance structures of the enolate formed from the following reaction: 7. (4 pts) Draw the structure of an alkyl bromide (R-Br) and an alkoxide (R-O) that would provide the most efficient synthesis of the following ether by the Williamson ether synthesis. Target ether 8. (5 pts.) Draw a mechanism for the following E2 reaction. Draw the major product. Be sure to include any necessary H's in your structure as you draw the mechanism. OH...
7. Which of the following alkenes will evolve the MOST heat during hydrogenation over Pd(0)? 8....
7. Which of the following alkenes will evolve the MOST heat during hydrogenation over Pd(0)? 8. (3 pts) a. Draw the arrows that show the flow of electrons during the reaction of Cl2 with cis-2- butene leading to formation of the Reactive Intermediate. b. In the labeled box, provide the structure of the Reactive Intermediate initially formed upon reaction of Cl2 with cis-2-butene. c. Draw the arrows that show the flow of electrons during collapse of the Reactive Intermediate. d....
4. Provide a plausible mechanism for the reaction shown. (6 pts) 7 NaNH. Hycor ND 5....
4. Provide a plausible mechanism for the reaction shown. (6 pts) 7 NaNH. Hycor ND 5. Each transformation shown below requires at least two steps. Provide the reagents/conditions for each transformation. (20 pts) Reagents Reagents A! Reagents D-7 Reagents Reagents 6. Predict the products from the Birch reductions shown below. (3 pts) Nz, NHU CH OH Bonus: (6 pts) Provide a synthesis for the target molecule using benzene. CO2H CO2H TM 1. Draw Frost circle diagrams for each compound shown....
14. The following sequence of reactions outlines a synthesis for the calcium-channel blocker Diltiazem, which is used...
14. The following sequence of reactions outlines a synthesis for the calcium-channel blocker Diltiazem, which is used to treat high blood pressure and to control angina (chest pain). A 1. NaH, THE 1 OH CI pyridine 2. p-methoxy- benzaldehyde 4 ~ SH -NO2 H2 p-TsOH muy a BTSCH o Han Pd-C heat OCH COCH3 OCH Ac20 1. Nah E- -OH pyridine 2. F Diltiazem a) (14 points) Propose suitable reagents and structures for the missing intermediates. Reagent(s) A: Reagent(s) B:...
Paragraph Styles 6. ... 7 1. Why is an ester less reactive to nucleophilic acyl substitution...
Paragraph Styles 6. ... 7 1. Why is an ester less reactive to nucleophilic acyl substitution than an acid chloride? A) Chloride is a better leaving group B) Oxygen is better at donating electron density into the carbonyl with added resonance stability. C) Chloride is a better leaving group and compared to chlorine, oxygen is better at donating electron density into the carbonyl with added resonance stability D) The alkoxy anion is less basic than the chloride anion. 2. What...
Question 7 4 pts For the following reaction sequence, which molecule is expected as the major...
Question 7 4 pts For the following reaction sequence, which molecule is expected as the major product? Br 1) t-BuOK 2a) Oso 2b) NaHSO3, H20 OH OH Br OH HO (a) (b) (c) (d) (a) (b) (c) (d) 4 pt D Question 8
The Malonic Acid synthesis is similar to the Acetoacetic Ester synthesis It uses diethyl malonate as the main starting material Draw the structure of diethyl malonate (malonic ester) Diethyl malonate can be hydrolyzed back to malonic acid and if heat is applied after the hydrolysis, will decarboxylate. Draw the mechanism for this transformation starting with malonic acid. Indicate the new C-C bonds in each molecule and then provide the organohalides which were used to synthesize each compound using the malonic...
12) Provide the structure of the major organic product in the reaction below. РОС Is 13) Chromic acid oxidations are believed to proceed through a chromate ester intermediate. In its conversion to the intermediate aldehyde. Answer n-1-ol, provide the structure of this ester and give the mechanism for 14) What series of synthetic steps could be used to carry out the transformation shown below? Answer (three steps): 2. 3. 15) Reaction of ethylmagnesium bromide with which of the following compounds...
Claisen Condensations Claisen condensations involve the enolate anion of an ester which acts as a nucleophile attacking another molecule of ester. The resulting product of this reaction is a Beta-ketoester. Draw the enolate anion which serves as the nucleophile in the reaction above. Draw the resonance structure of this enolate. Look at the mechanism of this reaction in your textbook (7^th edition), pages 773-774. What type of reaction does this resemble, S_N1,S_N2, E1, or E2? Ethanol is one of the...
Show the product of reaction of the indicated ester with LDA,
followed by butyl iodide.
CHÚCH 0 1. Provide a correct name for the indicated ester. 2. How many signals would we expect to see in the 13C NMR spectrum? 3. Show the combination of reagents required to synthesize the indicated structure using a Fischer esterification reaction. 4. a. The indicated ester is submitted to Claisen condensation conditions, using the appropriate alkoxide base and a second acidification step. The product...
6. (4 pts.) Draw the two resonance structures of the enolate formed from the following reaction: 7. (4 pts) Draw the structure of an alkyl bromide (R-Br) and an alkoxide (R-O) that would provide the most efficient synthesis of the following ether by the Williamson ether synthesis. Target ether 8. (5 pts.) Draw a mechanism for the following E2 reaction. Draw the major product. Be sure to include any necessary H's in your structure as you draw the mechanism. OH...
7. Which of the following alkenes will evolve the MOST heat during hydrogenation over Pd(0)? 8. (3 pts) a. Draw the arrows that show the flow of electrons during the reaction of Cl2 with cis-2- butene leading to formation of the Reactive Intermediate. b. In the labeled box, provide the structure of the Reactive Intermediate initially formed upon reaction of Cl2 with cis-2-butene. c. Draw the arrows that show the flow of electrons during collapse of the Reactive Intermediate. d....
4. Provide a plausible mechanism for the reaction shown. (6 pts) 7 NaNH. Hycor ND 5. Each transformation shown below requires at least two steps. Provide the reagents/conditions for each transformation. (20 pts) Reagents Reagents A! Reagents D-7 Reagents Reagents 6. Predict the products from the Birch reductions shown below. (3 pts) Nz, NHU CH OH Bonus: (6 pts) Provide a synthesis for the target molecule using benzene. CO2H CO2H TM 1. Draw Frost circle diagrams for each compound shown....
14. The following sequence of reactions outlines a synthesis for the calcium-channel blocker Diltiazem, which is used to treat high blood pressure and to control angina (chest pain). A 1. NaH, THE 1 OH CI pyridine 2. p-methoxy- benzaldehyde 4 ~ SH -NO2 H2 p-TsOH muy a BTSCH o Han Pd-C heat OCH COCH3 OCH Ac20 1. Nah E- -OH pyridine 2. F Diltiazem a) (14 points) Propose suitable reagents and structures for the missing intermediates. Reagent(s) A: Reagent(s) B:...
Paragraph Styles 6. ... 7 1. Why is an ester less reactive to nucleophilic acyl substitution than an acid chloride? A) Chloride is a better leaving group B) Oxygen is better at donating electron density into the carbonyl with added resonance stability. C) Chloride is a better leaving group and compared to chlorine, oxygen is better at donating electron density into the carbonyl with added resonance stability D) The alkoxy anion is less basic than the chloride anion. 2. What...
Question 7 4 pts For the following reaction sequence, which molecule is expected as the major product? Br 1) t-BuOK 2a) Oso 2b) NaHSO3, H20 OH OH Br OH HO (a) (b) (c) (d) (a) (b) (c) (d) 4 pt D Question 8
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