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
Organic Chemistry
- Phenacetin is an analgesic compound having molecular formula C10H13NO2. Once a common component in over-the-counter pain relievers such as APC (aspirin, phenacetin, caffeine), phenacetin is no longer used because of its liver toxicity. Deduce the structure of phenacetin from its 1H NMR and IR spectra.arrow_forwardThe two most general amine syntheses are the reductive amination of carbonyl compounds and the reduction of amides.Show how these techniques can be used to accomplish the following syntheses.(a) benzoic acid S benzylamine (b) benzaldehyde S benzylamine(c) pyrrolidine S N@ethylpyrrolidine (d) cyclohexanone S N@cyclohexylpyrrolidine(e) HOOC¬(CH2)3 ¬COOH S pentane@1,5@diamine (cadaverine)arrow_forwardFollowing 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_forward
- Arrange the following in increasing order of boiling point. Give reason. Methylamine, trimethylamine, dimethylamine Arrange the following in increasing order of basicity. Give reason. Methylamine, trimethylamine, dimethylamine Arrange the following in increasing order of solubility in H2O. Give reason. Methylamine, trimethylamine, dimethylaminearrow_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_forwardBarbiturates are prepared by treatment of diethyl malonate or a derivative of diethyl malonate with urea in the presence of sodium ethoxide as a catalyst. Following is an equation for the preparation of barbital, a long-duration hypnotic and sedative, from diethyl diethylmalonate an urea. Barbital is prescribed under one of a dozen or more trade names. Propose a mechanism for This reaction The pKa of barbital is 7.4. Which is the most acidic hydrogen in this molecule and how do you account for its acidity?arrow_forward
- Show how Gabriel syntheses are used to prepare the following amines.(a) benzylaminearrow_forwardArrange the following compounds in the increasing order of their acid strength: p-cresol, p-nitrophenol, phenolarrow_forwardThe 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_forward
- Nonearrow_forwardDiscovery of the antibiotic sulphanilamide led to rapid development of a large number of structurally related sulphonamides. Some of these were useful leads to compounds with other medicinal properties. Amongst these, sulfasalazine was active in the treatment of ulcerative colitis, a potentially fatal disease of the colon. As a medicinal chemist, you are about to carry out the synthesis of sulfasalazine, starting from aniline. Give the chemical names and draw the chemical structures of the reagents you will need to use for the all the steps marked (a)-(d). Aniline HO₂C HO (a) N=N- ACHN Ac represents CH3CO Sulfasalazine SO,NH S0,C1 N (b) (d) H₂N- SO,NH (c) N [Oro] SO,NH N Step (a) in question 5 above results in the para product only. Explain why this occurs.arrow_forwardParoxetine (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_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