(a)
Interpretation:
The preparation of haloperidol compound has to be proposed.
Concept Introduction:
Retrosynthetic analysis:
In an
(b)
Interpretation:
The chirality of haloperidol, and the possible of number of isomers in the given synthesis has to be given.
Concept Introduction:
Stereoisomers and chiral:
Isomers differing only in their spatial arrangement of atoms are called as stereoisomers.
The geometric property of a molecule that cannot be superimposed on its mirror image is known as chirality. Chiral carbon is the one which is attached with four different groups or atoms.
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Chapter 22 Solutions
Organic Chemistry
- Following is the structure of miconazole, the active antifungal agent in a number of over-the-counter preparations, including Monistat, that are used to treat vaginal yeast infections. One of the compounds needed for the synthesis of miconazole is the trichloro derivative of toluene shown on its right. (a) Show how this derivative can be synthesized from toluene. (b) How many stereoisomers are possible for miconazole?arrow_forwardFollowing is the structural formula of Surfynol, a defoaming surfactant. Describe the synthesis of this compound from acetylene and a ketone. How many stereoisomers are possible for Surfynol?arrow_forward-Ocimene is a pleasant-smelling hydrocarbon found in the leaves of certain herbs. It has the molecular formula C10H16 and a UV absorption maximum at 232 nm. On hydrogenation with a palladium catalyst, 2,6-dimethyloctane is obtained. Ozonolysis of -ocimene, followed by treatment with zinc and acetic acid, produces the following four fragments: (a) How many double bonds does -ocimene have? (b) Is -ocimene conjugated or nonconjugated? (c) Propose a structure for -ocimene. (d) Write the reactions, showing starting material and products.arrow_forward
- - Identify compounds J & K - Draw a curved arrow mechanism that accounts for the formation of J (take into account stereochemical considerations)arrow_forwardDoxaprost, an orally active bronchodilator patterned after the natural prostaglandins , is synthesized in the following series of reactions starting with ethyl 2-oxocyclopentanecarboxylate. Except for the Nef reaction in Step 8, we have seen examples of all other types of reactions involved in this synthesis. Q. Assuming that the two side chains on the cyclopentanone ring are trans, how many stereoisomers are possible from this synthetic sequence?arrow_forwardγ-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 γ-butyrolactone is more fat soluble than GHB, it is more readily absorbed by tissues and thus produces a faster onset of physiological symptoms. γ-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 γ-butyrolactone?arrow_forward
- Plants extract are widely used in many parts of Cameroon to treat infectious disease or related symptoms including abdominal pains, itching, urinary and respiratory ailments, fever, coughing and diarrhea. Harunmadagascarin C as depicted below is an extract from the plant Harungana madagascariensis that has been studied for potential antimicrobial activity. Which statement best describes the stereochemistry of the compound? a. Harunmadagascarin C is achiral and does not have any stereogenic or chiral centers. b. The two stereogenic centers are currently in the E configuration, and the double bond in the ring structure is not stereogenic. c. There are four possible stereoisomers for Harunmadagascarin C since, as depicted, there are 2 stereocenters in the compound. d. There is one chiral center present in the molecule.arrow_forwardCompound A, C8H10O, has the IR and 1H NMR spectra shown. Propose a structure consistent with the observed spectra, and label each peak in the NMR spectrum. Note that the absorption at 5.5 î disappears when D2O is added.arrow_forwardDrawing an SN2 product with More Complex Reactants Identify C, the product of an SN2 reaction in the synthesis of raloxifene, a drug used to reduce the risk of invasive breast cancer in postmenopausal women.arrow_forward
- When pure (S)-lactic acid is esterified by racemic butan-2-ol, the product is 2-butyl lactate, with the following structure:H+CH3 CH COOH CH3 CH CH3 CH CHOH OHCH2CH3 CH2CH3lactic acidC OOH CH O 3butan-2-ol 2-butyl lactate+(a) Draw three-dimensional structures of the two stereoisomers formed, specifying the configuration at each asymmetriccarbon atom. (Using your models may be helpful.)(b) Determine the relationship between the two stereoisomers you have drawnarrow_forwardCompound J, C16H16Br2, is optically active. On treatment with strong base, compounds K and L (each C16H14) are formed; K and L each absorb only 2 equivalents of hydrogen when reduced over a Pd/C catalyst. Compound K reacts with ozone to give phenylacetic acid (C6H5CH2COOH), while similar treatment of L gives 2 products. One product, M, is an aldehyde with formula C7H6O; the other product is glyoxal (CHO)2. Draw the structure of compound L.arrow_forwardIdentify compounds A – E of the reaction sequence shown in Scheme III, making sure to include stereochemistry as appropriate.a) Identify compound A in Scheme III. b) Identify compound B in Scheme III. c) Identify compound C in Scheme III. d) Identify compound D in Scheme III. e) Identify compound E in Scheme III.arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning