Interpretation:
A synthesis of diethylcarbamazine from the given starting materials has to be given.
Concept introduction:
Retro synthesis: It is a technique of planning an
Base catalysed ring opening of
The nucleophile will attack at the less substituted position under basic conditions and then the alkoxide ion gets proton from alcohol which form the product.
Acid chlorides are most often prepared by treating a
Chloroformates:
They are the class of organic compounds which are colourless and having a formula
Reaction of Chloroformates with
The product will be carbamates.
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Chapter 18 Solutions
EP ORGANIC CHEMISTRY-OWL V2 ACCESS
- Following is a synthesis for toremifene, a nonsteroidal estrogen antagonist whose structure is closely related to that of tamoxifen. (a) This synthesis makes use of two blocking groups, the benzyl (Bn) group and the tetrahydropyranyl (THP) group. Draw a structural formula of each group and describe the experimental conditions under which it is attached and removed. (b) Discuss the chemical logic behind the use of each blocking group in this synthesis. (c) Propose a mechanism for the conversion of D to E. (d) Propose a mechanism for the conversion of F to toremifene. (e) Is toremifene chiral? If so, which of the possible stereoisomers are formed in this synthesis?arrow_forwardCompound H (C8H6O3) gives a precipitate when treated with hydroxylamine in aqueous ethanol and a silver mirror when treated with Tollens solution. Following is its 1H-NMR spectrum. Deduce the structure of compound H.arrow_forwardThe following three derivatives of succinimide are anticonvulsants that have found use in the treatment of epilepsy, particularly petit mal seizures. Q. Of these three anticonvulsants, one is considerably more acidic than the other two. Which is the most acidic compound? Estimate its pKa and account for its acidity. How does its acidity compare with that of phenol? with that of acetic acid?arrow_forward
- The following questions concern ethyl (2-oxocyclohexane)carboxylate.(a) Write a chemical equation showing how you could prepare ethyl (2-oxocyclohexane)-carboxylate by a Dieckmann cyclization.(b) Write a chemical equation showing how you could prepare ethyl (2-oxocyclohexane)-carboxylate by acylation of a ketone.(c) Write structural formulas for the two most stable enol forms of ethyl (2-oxocyclohexane)carboxylate.(d) Write the three most stable resonance contributors to the most stable enolate derived from ethyl (2-oxocyclohexane)carboxylate.(e) Show how you could use ethyl (2-oxocyclohexane)carboxylate to prepare 2-methylcyclohexanone.(f) Give the structure of the product formed on treatment of ethyl (2-oxocyclohexane)-carboxylate with acrolein (H2C=CHCH=O) in ethanol in the presence of sodium ethoxidearrow_forwardAtenolol is a beta blocker medication primarily used to treat high blood pressure and heart- associated chest pain. Other uses include the prevention of migraines and treatment of certain irregular heart beats It is taken by mouth or by injection into a vein. It can also be used with other blood pressure medications. OH .N. CH3 ČH3 H2N° suggest industrial synthetic approach towards synthesis of this drug (atenolol) and provide reasons and advantages of your proposed synthetic approach.arrow_forwardMethamphetamine is a long-lasting, potent stimulant sold as a street drug. The synthesis is quite simple and one step in the synthesis is shown below. Using your knowledge of the reactions of amines, provide all the reagents necessary to complete the reaction below. Provide the reagents for step 1 and step 2 ,arrow_forward
- Propose single-step and multistep syntheses of acid derivatives from compoundscontaining other functional groups. Propose multistep syntheses using acid derivatives as starting materials and intermediates.arrow_forwardCompound A undergoes an acid-catalyzed hydrolysis. One of the products (B) that is isolated gives the following 1H NMR spectrum. Identify the compounds A and Carrow_forwardEnanthotoxin is an extremely poisonous organic compound found in hemlock water drop- wart, which is reputed to be the most poisonous plant in England. It is believed that no British plant has been responsible for more fatal accidents. The most poisonous part of the plant is the roots, which resemble small white carrots, giving the plant the name"five finger death."Also poisonous are its leaves, which look like parsley. Enanthotoxin is thought to interfere with the Nat current in nerve cells, which leads to convulsions and death. он How many stereoisomers are possible for enanthotoxin?arrow_forward
- Paroxetine (Paxil) is an antidepressant that is a member of a family of drugs known as Selective Serotonin Reuptake Inhibitors (SSRIS). This family of drugs also includes fluoxetine (Prozac) and sertraline (Zoloft). SSRIS work by inhibiting the reuptake of the neurotransmitter serotonin in the synapses of the central nervous system follow- ing release of serotonin during excitation of individual nerve cells. Between firings, the serotonin is taken back up by a nerve cell in preparation for firing again. Inhibition of reuptake has the effect of increasing the time serotonin molecules remain in the syn- apses following excitation, leading to a therapeutic effect. In one synthesis of parox- etine, the following reagents are used. Draw the structures of synthetic intermediates A and B. F НО SOCI, A B HO Pyridinearrow_forwardVerapamil, a coronary artery vasodilator, is used in the treatment of angina caused by insufficient blood flow to cardiac muscle. Even though its effect on coronary vasculature tone was recognized over 30 years ago, only recently has its role as a calcium channel blocker become understood. Following is a retrosynthetic analysis leading to a convergent synthesis; it is convergent because (A) and (B) are made separately and then combined (i.e., the route converges) to give the final product. Convergent syntheses are generally much more efficient than those in which the skeleton is built up stepwise. Q. Two steps are required to convert (D) to (C). The first is treatment of (D) with ethyl chloroformate. What is the product of this first step? What reagent can be used to convert this product to (C)?arrow_forwardVerapamil, a coronary artery vasodilator, is used in the treatment of angina caused by insufficient blood flow to cardiac muscle. Even though its effect on coronary vasculature tone was recognized over 30 years ago, only recently has its role as a calcium channel blocker become understood. Following is a retrosynthetic analysis leading to a convergent synthesis; it is convergent because (A) and (B) are made separately and then combined (i.e., the route converges) to give the final product. Convergent syntheses are generally much more efficient than those in which the skeleton is built up stepwise. Q. How do you account for the regioselectivity of the nucleophilic displacement involved in converting (C) to (B)?arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage LearningIntroduction to General, Organic and BiochemistryChemistryISBN:9781285869759Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar TorresPublisher:Cengage Learning
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