Rimantadine was among the first antiviral drugs to be licensed in the United States to use against the influenza A virus and to treatestablished illnesses. It is synthesized from adamantane by the following sequence:Br2(1)BrAdamantane1-bromoadamantaneCH,—CHBrAlBr3(3)(2)Br-BrNH₂(5)(4)Rimantadinea Step 2 proceeds via the following mechanism:1. AlBra acts as a Lewis acid to yield carbocation 1;2. Bromoethene acts as a nucleophile to give carbocation 2:3. Carbocation 2 reacts with nucleophile 3 to give the product of reaction 2.Work out this mechanism on a separate sheet of paper and then draw the structure of nucleophile 3.

Experimental condition to achieve step 3 product would be by reacting with sodium amide in the…

Rimantadine was among the first antiviral drugs to be licensed in the United States to use against the influenza A virus and to treat established illnesses. It is synthesized from adamantane by the following sequence: Br₂ 0 (1) -Br 1-bromoadamantane Adamantane CH,—CHBr AlBr3 (2) Br -Br

Rimantadine was among the first antiviral drugs to be licensed in the United States to use against the influenza A virus and to treat established illnesses. It is synthesized from adamantane by the following sequence: Br₂ 0 (1) -Br 1-bromoadamantane Adamantane CH,—CHBr AlBr3 (2) Br -Br

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...

See similar textbooks

Related questions

Q: Several drugs are prepared by reactions in which the formation of the carbon-carbon bond is the last…

A: The Mestranol is an oral contraceptive. It is also known as birth control pills. The IUPAC name of…

Q: Name the product of the reaction between cyclopentene and OsO4 (+ NaHSO3):

Q: Molecular Formula: C7H6N2 4 2 T 4000 3000 2000 1000 CM 9 8 7 6 5 4 3 2 1 0 6 N

A: From the given formula first calculate the degree of unsaturation as shown below, IHD =…

Q: MEDI H H H н—с — —с —сэ с—с—н H H H -C-H H name the following IUPAC rules ill H -U -

Q: The hydrocarbon whose formula is shown was subjected to complete hydrogenation. Use the given data…

Q: DHA is a fatty acid derived from fish oil and an abundant fatty acid in vertebrate brains.…

A: One molecule of DHA undergoes ozonolysis to obtain following products.

Q: Which of the following structural features could be found in a compound with formula C7H12? Group…

A: Unsaturated compounds are those which contain double bond, triple bond or a ring. Degree of…

Q: NH₂ ملا لمال SH .OH pyridine (1 eq)

A: There is more than one question and as per answering guidelines, I can answer only first three…

Q: Tell if the reaction is positive or not: 4-Heptyne and water 4-Heptyne and NaOH Isobutane and CHCl3

A: Note: as you have not specified any particular subpart, I am solving first three subparts (as per…

Q: OH NaOH (aq) 2 products

A: Estherification reaction refers to the formation of ester (RCOOR') on reaction of carboxylic acid…

Q: The terpinenes are compounds with the formula C₁0H16 which can be extracted from various plant…

Q: Write chemical structures for compounds A through D in the following sequence of reac- tions.…

A: Here there are two alcohols, A and C. Alcohol A reacts with NaNH2 and produces NH3 and B. So, B…

Q: When HBr is added to the following molecule:

A: Alkenes are the organic compounds which contain one or more double bond. The reaction of these…

Q: Draw the structures of the following heterocyclic compounds: 1- 2-…

Q: Name the product of the reaction between cyclopentene and OsO4 (+ NaHSO3):

Q: OH Cl2 (а) FeCl3 CH3

Q: Which of the following compounds are NOT aromatic? N. A A only OC, D, and E A and C C and D O B, C,…

Q: Use resonance structures to predict the products of the following reaction: N Indole H +

A: Electrophilic substitution reaction of indole.By drawing the resonance structures of indole the to…

Q: What is the unsaturation number of each of these compounds? C7H16

A: The degree of unsaturation can be defined as the total number of pi bonds and rings present in a…

Q: Order each of the following compounds from the most disordered (1) to the least disordered (4):…

A: Entropy of a system is the measure of disorderness of the system. The degree of disorderness…

Q: When 1, 2-dichlorooctane is treated with potassium hydroxide in aqueous ethanol, a mixture of three…

Q: Draw the structures of the products obtained from the following reaction:

A: In this chemical reaction, I- acts as leaving group whereas CH3OH acts as nucleophile, so ether will…

Q: Much of our understanding of conformational analysis has arisen from studies on the reactions of…

A: The steroidal moiety builds the concept of trans-diaxial ring opening of epoxy-cycloalkanes. The…

Q: Draw the indicated number of resonance structures for each species:

A: Resonance is the delocalization of electrons. Resonance structures arise when there is more than one…

Q: 1A Draw the structure of the following compounds: i) 5-ethyl-2-methoxy-3-nitrofuran ii)…

A: This problem is based on General Organic Chemistry. Here, we have to draw the structure from the…

Q: C₂H4(a) + H₂O(g) → C₂H5OH(a)

Q: Name the product of the reaction between cyclopentene and OsO4 (+ NaHSO3):

A: Cyclopentene reacts with OsO4 and NaHSO3 to give syn 1,2-diol.

Q: The so-called bombicol, which is the sex pheromone secreted by the female silkworm moth, has the…

A: E-Configuration: Groups with the same priority on the two alkenic carbons are on opposite sides…

Q: „NO2 *NO2 NO2 NO2 11 13 14

A: Let us considered the resonating structures to understand the reactivity of the following…

Q: pyruvic acid NaBH4 CH₂OH H₂SO4 (cat) C6H8O4 (show structure)

A: The problem is based on the general organic chemistry and here in the first step reduction of ketone…

Q: Several diamines are building blocks for the synthesis of pharmaceuticals and agro- chemicals. Show…

Q: Draw the structural formula of compounds Q,R,T,U and W

A: Structural formula of the compound is the one which shows all the atoms present in the compound and…

Q: Which of the following is the condensation product formed from two moles of Acetophenone (C6H5COCH3)…

A: Solution : Aldol reaction is one of the types of condensation reactions that involve the…

Q: Can i get help with these problems

Q: Draw the structures of the following heterocyclic compounds: 1- 2- 1,2,4-Dioxazolidine…

A: Since you have posted a question with multiple sub-parts, we will solve first three sub-parts for…

Q: Can you Propose a mechanism for these problems?

A: Benzene is an electron-rich compound as it contains three pi-bonds. It usually undergoes an…

Q: How many possible stereoisomers can be written for 1-ethyl-3- methylcyclohexane? O2 4 8.

Q: How are the following conversions carried out?(i) Propene → Propan-2-ol(ii) Benzyl chloride → Benzyl…

A: (i) Propene → Propan-2-ol

Question

Rimantadine was among the first antiviral drugs to be licensed in the United States to use against the influenza A virus and to treat
established illnesses. It is synthesized from adamantane by the following sequence:
Br2
(1)
Br
Adamantane
1-bromoadamantane
CH,—CHBr
AlBr3
(3)
(2)
Br
-Br
NH₂
(5)
(4)
Rimantadine
a Step 2 proceeds via the following mechanism:
1. AlBra acts as a Lewis acid to yield carbocation 1;
2. Bromoethene acts as a nucleophile to give carbocation 2:
3. Carbocation 2 reacts with nucleophile 3 to give the product of reaction 2.
Work out this mechanism on a separate sheet of paper and then draw the structure of nucleophile 3.

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 Introduction

VIEW

Step 2 Explanation

VIEW

Step 3 Answer

VIEW

Step by step

Solved in 3 steps with 1 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

Draw the structure of 2-azacyclopentanone, g-butyrolactam:
Chlorine is a catalytic pathway for the destruction of ozone. Show how the photodissociation of a molecule of C2F2C12 can destroy two molecules of ozone, O3.
What is the product?
Sorbitol is a sweetener often used in chewing gum and diet drinks. It is obtained by the following reaction. Which of the following functional group transformations occur during this reaction? СНО CH2OH Н-с-ОН Н-с-ОН Но-с-н Н2 Но-с-н Н-с-ОН Н-с-оН Н-с-ОН н-с-он CH2OH CH-Он glucose sorbitol a. The aldehyde becomes an alcohol. b. An alcohol becomes an aldehyde. c. An alcohol disappears. d. A new aldehyde appears. e. All of the above
What is the formula for a chemical reaction of L-theanine + Caffeine? Molecular Formula L- C7H14N2O3 Theanine Molecular Formula Caffeine C8H10N402
Potassium sorbate is added as a preservative to certain foods to prevent bacteria and molds from causing food spoilage and to extend the foods’ shelf life. The IUPAC name of potassium sorbate is potassium (2E,4E)-2,4-hexadienoate. Draw a structural formula for potassium sorbate.
what is the reagent of the bicyclic compound
Compare what will happen to the entropy of the whole system in the following two scenarios: A) if the oil molecules are all clumped together and the clump is surrounded by water and B) if the oil molecules are spread out evenly throughout the water, each individual oil molecule surrounded by water?
How do you draw this product on Mastering Chemistry?
Complete the following scheme!
Name the following molecule: 7-methyloctan-4-one O 2-methyloctan-5-one O 6-isopropylhexan-4-one 7-methyloctanone O 1,1-dimethylheptan-4-one