15.22 Polycyclic hydrocarbon derivatives are used as medication for viral infections. A com- pound that inactivates viruses was synthesized by the following sequence of reactions. What is its structure? CH₂ CH3 CH₂NH₂ (2 molar equivalents) diethyl ether LIAIH tetrahydrofuran H₂O ?

15.22 Polycyclic hydrocarbon derivatives are used as medication for viral infections. A com- pound that inactivates viruses was synthesized by the following sequence of reactions. What is its structure? CH₂ CH3 CH₂NH₂ (2 molar equivalents) diethyl ether LIAIH tetrahydrofuran H₂O ?

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter18: Functional Derivatives Of Carboxylic Acids

Section: Chapter Questions

Problem 18.30P: Nicotinic acid, more commonly named niacin, is one of the B vitamins. Show how nicotinic acid can be...

See similar textbooks

Related questions

Q: What is the IUPAC name of the following compound? 2-methyl-4,5-dimethylpent-1-ene…

A: Correct iupac name will be (E)-3, 4-dimethylhex-2-ene

Q: Give an 1-2 sentence explanation each of the effects/reactions in iodine test in Glucose, fructose,…

A: The iodine test is commonly used to detect the presence of starch, a complex polysaccharide.…

Q: 7. What variables can cause the pH range of an indicator to shift?

A: The pH range of an indicator is determined by its chemical structure and properties. However,…

Q: The Pauli Exclusion Principle tells us that no two electrons in an atom can have the same four…

A: Four types of Quantum numbers : Principal quantum number(n): It defines the number of shells in an…

Q: © Macmillan Learning You need to prepare an acetate buffer of pH 5.36 from a 0.662 M acetic acid…

Q: Match the orbitals below with their kind and identify their shapes. Put letters in alphabetical…

A: The shape of S orbital. The boundary surface diagram for the s orbital looks like a sphere having…

Q: Which of the following are actual "ideal gasses"? Choose them all. Ar 69 Ne H₂O N₂ F₂ NaCl All of…

A: We have to find ideal gases among the given gases.

Q: Concentrated hydrochloric acid is an aqueous solution that is 38.40 % HCl. The density of the…

A: Answer:- This question is answered by using the simple concept of calculation of mass using the mass…

Q: Macmillan Learni Loudon | Parise SEVENTH EDITION For trans-1-ethyl-4-isopropylcyclohexane, which…

Q: 10. Zn504.7H20 (1 g, 288 g/mol) was dissolved in 100 mL solution. (10) mL was titrated with 53 mL)…

A: ZnSO4.7H2O was titrated With EDTA

Q: Compare the structures of the fatty acids A and B below. Based on your conceptual understanding of…

A: We have find out the answer.

Q: A particular reaction is considered at 298 K. It has a deltaH° = -20 kJ and a deltaS° = -0.05 kJ/K.…

Q: Select the choice that best describes the relationship of the pair of compounds. H₂ H2C=CHCH2CH2CH3…

A: From the given options : A) Consitutional Isomers : these are the compounds that have same…

Q: The following compound can be synthesized from benzene and organic alcohols containing four or fewer…

Q: c) What will be the product in the following reaction? CH3 das. i KOH/methanol CH,=CH-C-CH,…

A: An extension of Michael addition is called Robinson annulation. This reaction is used in organic…

Q: Explain the concept of aromaticity in organic chemistry and provide a theoretical example of a…

A: Aromaticity is a fundamental concept in organic chemistry that explores the unique stability and…

Q: Draw a structural formula for the major organic product(s) of the reaction shown below. 1. CH3l…

A: Alkyl amines react with excess of methyl iodide followed by treatment with Ag2O,water,heat to give…

Q: ii. Which is the major product of this reaction? Ph OEt 1) 2 eq. PhMgl 2) H3O+ OH Ph Ph. OH Ph

Q: Write out the complete Bonding Scheme for the following compound. :0: 6,7 || H ; C = C 5 C 8 H =…

A: One single bond contains 1 sigma bond.One double contains one sigma bond and one pi bond.Triple bond…

Q: The eclipsed conformation of one of the following molecules (along the 1,2 C-C bond) is unusually…

A: According to Q&A guidelines of Bartleby, we are supposed to answer only the first question out…

Q: A chemist prepares a solution of sodium carbonate (Na₂CO,) by weighing out 50.7 mg of sodium…

A: Concentration in g/L = mass of Solute/Volume of solution 1 g = 103 mg 1 L = 103 mL

Q: Each pictured Lewis structure is invalid. Identify the error in each case. wrong electron total…

A: Lewis dot structure .

Q: 10 Naphthalene, which gives moth balls their characteristic odor, has the formula C₁0Hg. Its…

A: Lewis Structure represent how the electrons and bonds are arranged around atoms in the molecule.

Q: [References] Use the References to access important values if needed for this question. It is often…

A: Scientific notation is a way of writing very large or very small numbers. A number is written in…

Q: 15.38 In research into the stereochemistry of nucleophilic reactions, the following reaction was…

A: We have find out the answer.

Q: Consider the pairs of structures shown. A B C D H pair A pair B pair C pair D H CH3 :O: Ï H₂C H and…

Q: Question 6 of 10 O Macmillan Learning > b) Which are polar molecules? H₂C C/C H CH CH3 CH₂ H|||| H…

A: In the given question we have to identify the polar molecule, we have to define the molecule will…

Q: Macmillan Learning Identify each pair of compounds as constitutional isomers, stereoisomers,…

A: Constitutional isomers are the compounds having the same molecular formula but differ from each…

Q: Which of the following sugars is least stable? А. B. OH HO Е. сновн он CH SH OH с. нон с НО. НОН.С с…

A: We have been given 5 structures of carbohydrates and we are asked to predict which of these 5…

Q: Urea is an organic compound widely used as a fertilizer. its solubility in water allows it to be…

A: Urea, also recognized as carbamide, is an organic compound with a chemical composition of CO(NH2)2.…

Q: h) Compound I reacts with chlorine in the presence of ultraviolet radiation to give several…

A: Alkanes when reacts with halogens in presence uv light, it will produces most substituted alkyl…

Q: Draw a mechanism for the oxidation of benzoin with concentrated nitric acid

Q: What is the name of the alkali metal that is in period 6? What is the name of the halogen that is in…

A: The name of the alkali metal that is in period 6? The name of the halogen that is in period 4? The…

Q: a) Show using free radical reaction how you can prepare benzyl bromide from toluene.…

A: Given :- a) toluene ——> benzyl bromide b) benzyl bromide ———> phenylmethanamine To show :-…

Q: F.Mg +_ CuSO4 → G.HCI + NaHCO3 → NaCl +_ CO₂ + _ H₂O

Q: student wishes to make a buffer that has a pH of 4.65. The student has HNO2 and NaNO2. Nitrous…

Q: Playing the role of a high school chemistry teacher, explain to your students how adding heat to a…

Q: Consider the molecule. CI Molecule A Consider the molecule. Molecule B Consider the molecule. CI…

A: Geometrical isomers are formed by different arrengment of atoms in space

Q: 1. What is the pH and pOH of a 0.0235 M HCI solution? 2. What is the pOH of a 6.50 x 10-3 M KOH…

A: The pH and pOH of the given solutions can be determined by considering the concentration of H+ and…

Q: Consider the resonance structures of formate. Y-Y H H Select the true statements about the resonance…

A: Resonance structures are formed when pi-electron cloud delocalises. Here formate ion forms two…

Q: What volume of water must be added to concentrated HCl solution to prepare 100 mL 0.955 M HCl…

A: It is a dilution problem. The dilution of any concentrated solution can be done by using water. Here…

Q: A closed system at 150 °C initially contained 10 g of NH4Cl(s) before reaching equilibrium. The…

A: Pure solids and liquids are not considered while writing the equilibrium constant expression.

Q: Crude oil is a source of many hydrocarbons. The skeletal formulae of some of these hydrocarbons are…

Q: 4.3 Explain the selectivity observed in the reactions below: OH ∞ Œ Br Br₂ (H₂O) OH Br not formed

Q: 11. What will be the product of the following synthesis? 4 A) B) C) D) 1. LAH 2 H₂0, Fr OH E) none…

A: LiAlH4 reduces carbonyl group to alcohol group. Alcohols on reaction with HBr give alkyl halide.…

Q: 20) How many a-cleavages are possible for this molecule? 'N

A: We have find out the answer

Q: Given the MS spectra below, show the fragmentation pattern responsible for m/z values Relative…

A: Mass spectrum is the technique used in analytical chemistry for the separation of ions based on the…

Q: Organic Molecule Name CH3 OH H3C-C-CH CH3 CH3 Br CH3 CH3-C-CH-CH3 C1 H3C нс I-O-I н H C С CH3 -О-І…

A: Following structural formula of the compounds given -

Q: A chemist combined chloroform (CHCl,) and acetone (C₂H₂O) to create a solution where the mole…

A: "Since you have asked multiple questions, we will solve the first question for you. If you want any…

Q: 1. Calculate the energy (in kJ) required to heat 0.399 grams of water from 103.2 ℃ to 153.0 ℃. 2.…

A: The heat evolved or absorbed is calculated by the multiplication of mass of the compound with its…

Question

15.22 Polycyclic hydrocarbon derivatives are used as medication for viral infections. A com-
pound that inactivates viruses was synthesized by the following sequence of reactions. What is its
structure?
CH₂ CH3
CH₂NH₂ (2 molar equivalents)
diethyl ether
LIAIH
tetrahydrofuran
H₂O
?

Expert Solution

This question has been solved!

Explore an expertly crafted, step-by-step solution for a thorough understanding of key concepts.

SEE SOLUTION Check out a sample Q&A here

Step 1: First part

VIEW

Step 2: Second part

VIEW

Solution

VIEW

Step by step

Solved in 3 steps with 3 images

SEE SOLUTION Check out a sample Q&A here

Knowledge Booster

Learn more about

Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.

Similar questions

Propranolol, an antihypertensive agent used in the treatment of highblood pressure, can be prepared from 1-naphthol, epichlorohydrin, andisopropylamine using two successive nucleophilic substitutionreactions. Devise a stepwise synthesis of propranolol from these startingmaterials
Ibufenac, a para-disubstituted arene with the structure HO2CCH2C6H4CH2CH(CH3)2, is a much more potent analgesic than aspirin, but it was never sold commercially because it caused liver toxicity in some clinical trials. Devise a synthesis of ibufenac from benzene and organic halides having fewer than five carbons.
Nicotinic acid, more commonly named niacin, is one of the B vitamins. Show how nicotinic acid can be converted to (a) ethyl nicotinate and then to (b) nicotinamide.
One of the products of petroleum refinery is naphtha where, benzene could beobtained via catalytic reforming of naphtha. The obtained benzene can potentiallyto react with Lewis acid to form new carbon-carbon bond. Propose the startingmaterial and stepwise mechanism to produce new chemical structure which consista formula molecule of C11H16.
Sulfur ylides, like the phosphorus ylides of Chapter 21, are useful intermediates in organic synthesis. Methyl trans-chrysanthemate, an intermediate in the synthesis of the insecticide pyrethrin I (Section 26.4), can be prepared from diene A and a sulfur ylide. Draw a stepwise mechanism for this reaction.
Sulfur ylides, like the phosphorus ylides, are usefulintermediates in organic synthesis. Methyl trans-chrysanthemate, anintermediate in the synthesis of the insecticide pyrethrin I,can be prepared from diene A and a sulfur ylide. Draw a stepwisemechanism for this reaction.
Identify compounds A, B, and C. a.Compound A has molecular formula C8H12 and reacts with two equivalents of H2. A gives HCOCH2CH2CHO as the only product of oxidative cleavage with O3 followed by CH3SCH3. b.Compound B has molecular formula C6H10 and gives (CH3)2CHCH2CH2CH3 when treated with excess H2 in the presence of Pd. B reacts with NaNH2 and CH3I to form compound C (molecular formula C7H12).
Identify compounds A, B, and C. a. Compound A has molecular formula C8H12 and reacts with two equivalents of H2. A gives HCOCH2CH2CHO as the only product of oxidative cleavage with O3 followed by CH3SCH3. b. Compound B has molecular formula C6H10 and gives (CH3)2CHCH2CH2CHCH3 when treated with excess H2 in the presence of Pd. B reacts with NaNH2 and CH3I to form compound C (molecular formula C7H12).
Identify compounds A, B, and C. a.) Compound A has molecular formula C8H12 and reacts with two equivalents of H2. A gives HCOCH2CH2CHO as the only product ofoxidative cleavage with O3 followed by CH3SCH3. b.) Compound B has molecular formula C6H10 and gives(CH3)2CHCH2CH2CH3 when treated with excess H2 in the presence ofPd. B reacts with NaNH2 and CH3I to form compound C (molecularformula C7H12).
Identify A, B, and C, three intermediates in the synthesis of the pain reliever and anesthetic fentanyl.
Suzuki coupling of aryl iodide A and vinylborane B affords compound C, which is converted to D in the presence of aqueous acid. Identify compounds C and D and draw a stepwise mechanism for the conversion of C to D.
What is the major alkene formed when A is treated with POCl3 andpyridine? Explain why the major product is different in these reactions.