(c) The sedative, R-thalidomide, was once used to address symptoms of morning sickness in expectant mothers, however, when it was discovered that S- thalidomide causes deformities in infants, the use of R-thalidomide as a sedative was discontinued. With the help of a reaction mechanism, explain why enantiopure R-thalidomide can not be safely used as a sedative without affecting infants
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- y-Butyrolactone (C4H6O2, GBL) is a biologically inactive compound that is converted to the biologically active recreational drug GHB (Section 19.5) by a lactonase enzyme in the body. Since y-butyrolactone is more fat soluble than GHB, it is more readily absorbed by tissues and thus produces a faster onset of physiological symptoms. y-Butyrolactone shows an absorption in its IR spectrum at 1770 cm-1 and the following 1H NMR spectral data: 2.28 (multiplet, 2 H), 2.48 (triplet, 2 H), and 4.35 (triplet, 2 H) ppm. What is the structure of y-butyrolactone?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 PyridineA key step in the hydrolysis of acetamide in aqueous acid proceeds by nucleophilic addition of * OH (a) H3O* to CH3Ĉ NH2 (b) H2O to CH3ČNH2 + OH +OH (c) H3O* to CH,ČNH2 (d) HO¯ to CH3CNH2
- 4) Multistriatin, one of the pheremones of the elm bark beetle, is a volatile compound released by a virgin female beetle when she has found a good food source - an elm tree. Male beetles, which carry the Dutch elm disease fungus, are attracted by the pheromone; the tree becomes infected with the fungus and soon dies. Multistriatin is used to trap the beetles, but the amount in beetles is so miniscule that the compound must be synthesized. The following synthesis of multistriatin uses only chemistry that we have seen in Chem 348. HO. НО Br type O type. H type H H CH3 H HO HO type O H CH3 "Η OH type H hint: anhydrous cond CH3 H = H type type HO CH3 H H type CH 3 H Multistriatin MultistriatinIn an attempt to synthesize compound C through a two-step process, a chemist discovered after completing the first step that they had inadvertently produced two distinct compounds, A and B. Upon examining the infrared spectroscopy (IR) results, it was observed that both A and B exhibited peaks indicative of a ketone and an ester group. Please provide the molecular structures of A and B. OEt NaOEt ΕΙΟ A B In a chemical experiment, they noticed that both components, A and B, from a combined sample turned into a new compound, C, during the following stage. The task is to determine what compound C looks like and explain how compound A or B changes into compound C through a reaction. Compound C should be the primary molecule containing carbon created in this process, not just a by-product. A B H3O+, H₂O, A Mechanism = с(c) Reaction of acetanilide with bromine Br: CH3 (d) Hydrolysis of 4-bromo-2-chloroacetanilide with HCl and ethanol HCI CH,CH,OH
- 1. Draw structures for the following: (a) N,N-dimethylpentanamide (b) Acetamide(c) 2,3-dimethylpentanamide (d) N-ethylbenzamideLook up the structure of lisdexamfetamine (Vyvanse), a drug used in the treatment of attention deficit hyperactivity disorder (ADHD). Redraw it and identify all the functional groups present. What is known about itstherapeutic properties?5 The compounds labeled benzophenone-3 (CH,O,) and benzophenone-5 (CHNAO,S) are found in certain sunscreens. Would you expect a sunscreen made with benzophenone-3 or benzophenone-5 to be more waterproof? Explain your choice.
- Phenacetin is an analgesic compound having molecular formula C10H13NO2. Once a common component in over-thecounter 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.Treating trimethylamine with 2-chloroethyl acetate gives acetylcholine as its chloride. Acetylcholine is a neurotransmitter. Me;N + CH,COCH,CH,CI C,H1,CINO, Acetylcholine chloride Propose a structural formula for this quaternary ammonium salt and a mechanism for its formation.A diuretic is a compound that causes increased urination and thereby reduces fluid volume in the body. An important use of diuretics in clinical medicine is in the reduction of the fluid buildup, particularly in the lungs, that is associated with congestive heart failure. It is also used as an antihypertensive (i.e., to reduce blood pressure). Furosemide, an exceptionally potent diuretic, is prescribed under 30 or more trade names, the best known of which is Lasix. The synthesis of furosemide begins with treatment of 2,4-dichlorobenzoic acid with chlorosulfonic acid in a reaction called chlorosulfonation. The product of this reaction is then treated with ammonia followed by heating with furfurylamine. Q. Is furosemide chiral? If so, which of the possible stereoisomers are formed in this synthesis?