9.46 Draw the substitution product formed (including stereochemistry) when (R)-hexan-2-ol is treated with each series of reagents: (a) NaH, followed by CH3l; (b) TsCI and pyridine, followed by NaOCH3; (c) PBг3, followed by NaOCH3. Which two routes produce identical products?
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- Devise a synthesis of (E)-tetradec-11-enal, a sex pheromone of thespruce budworm, a pest that destroys fir and spruce forests, fromacetylene, Br(CH2)10OH, and any needed organic compounds orinorganic reagents.Identify products A and B from the given 1H NMR data. Treatment of acetone [(CH3)2C=O] with dilute aqueous base forms B. Compound B exhibits four singlets in its 1H NMR spectrum at 1.3 (6 H), 2.2 (3 H), 2.5 (2 H), and 3.8 (1H) ppm. What is the structure of B?Devise a synthesis of (E)-tetradec-11-enal, a sex pheromone of the spruce budworm, a pest that destroys fir and spruce forests, from acetylene, Br(CH2)10OH, and any needed organic compounds or inorganic reagents.
- What steps are needed to prepare phenylacetylene, C6H5C = CH, from each compound: (a) C6H5CH2CHBr2; (b) C6H5CHBrCH3; (c) C6H5CH2CH2OH?lejimalide B, an anticancer agent with a 24-membered ring, is isolated from a tunicate found off le Island in Okinawa. (a) Label each double bond in iejimalide B as E or Z. (b) Label each tetrahedral stereogenic center as R or S. (c) How many stereoisomers are possible for iejimalide B? CH;0 CHO OCH, HO, iejimalide BDevise a synthesis of (E)-tetradec-11-enal, a sex pheromone of the spruce budworm, a pest that destroys r and spruce forests, from acetylene, Br(CH2)10OH, and any needed organic compounds or inorganic reagents.
- (a) Give an acceptable name for each compound, (b) Draw the organic products formed when A or B is treated with each reagent: [1] H3O+; [2] −OH, H2O; [3] CH3CH2CH2MgBr (excess), then H2O; [4] LiAlH4, then H2O.A step in a synthesis of PGE1 (prostaglandin E1, alprostadil) is the reaction of a trisubstituted cyclohexene with bromine to form a bromolactone. Propose a mechanism for formation of this bromolactone and account for the observed stereochemistry of each substituent on the cyclohexane ring. Alprostadil is used as a temporary therapy for infants born with congenital heart defects that restrict pulmonary blood flow. It brings about dilation of the ductus arteriosus, which in turn increases blood flow in the lungs and blood oxygenation.Heating compound X with aqueous formaldehyde forms Y (C17H23NO),which has been converted to a mixture of lupinine and epilupinine,alkaloids isolated from lupin, a perennial ornamental plant commonlyseen on the roadside in parts of Alaska . Identify Y and explain how it is formed.
- When (R)-6-bromo-2,6-dimethylnonane is dissolved in CH3OH,nucleophilic substitution yields an optically inactive solution. When theisomeric halide (R)-2-bromo-2,5-dimethylnonane is dissolved in CH3OHunder the same conditions, nucleophilic substitution forms an opticallyactive solution. Draw the products formed in each reaction, and explainwhy the difference in optical activity is observed.When acetonitrile is treated with concentrated sulfuric acid and tert-butanol, followed by water, a product is formed whose 'H NMR spectrum exhibits the following three signals: singlet, 1.3 ppm, 9 H; singlet, 2.0 ppm, 3 H; and broad singlet, 8.2 ppm, 1 H. Its IR spectrum exhibits one broad absorption of medium intensity between 3300 and 3500 cm-1, and a narrow, intense absorption near 1650 cm¯1. A key intermediate is shown. Draw the structure of the product, and draw the complete, detailed mechanism for the reaction. CH3 CH3 H2SO4 (conc) H2O ? + H3C H3C H3C-C=Ñ-c `CH3 CH3 HOSeveral sulfonylureas, a class of compounds containing RSO2NHCONHR, are useful drugs as orally active replacements for injected insulin in patients with adult-onset diabetes. These drugs decrease blood glucose concentrations by stimulating b cells of the pancreas to release insulin and by increasing the sensitivity of insulin receptors in peripheral tissues to insulin stimulation. Tolbutamide is synthesized by the reaction of the sodium salt of p-toluenesulfonamide and ethyl N-butylcarbamate . Propose a mechanism for this step.