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- 2-bromo-2-methylbutane undergoes hydrolysis reaction with water, H2O toform compound W. Compound X and compound Y are produced when 2-bromo-2-methylbutane undergoes elimination reaction with alcoholic ofsodium hydroxide, NaOH. (ii) What is the type of reaction involved in the formation of compound W? (iii) Identify the major product of the elimination reaction between compound Xand compound Y based on Zaitsev’s rule.Give the major product when 2-bromobutanal reacts with acidic aqueous KCN.Acid-catalyzed hydrolysis of the following epoxide gives a trans diol. Of the two possible trans diols, only one is formed. How do you account for this stereoselectivity?
- -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.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.The following equation shows the reaction of trans-2,3-diphenyloxirane with hydrogen chloride in benzene to form 2-chloro-1,2-diphenylethanol. (a) How many stereoisomers are possible for 2-chloro-1,2-diphenylethanol? (b) Given that opening of the epoxide ring in this reaction is stereoselective, predict which of the possible stereoisomers of 2-chloro-1,2-diphenylethanol is/are formed in the reaction.
- When cis-2-decalone is dissolved in ether containing a trace of HCl, an equilibrium is established with trans-2-decalone. The latter ketone predominates in the equilibrium mixture. Propose a mechanism for this isomerization and account for the fact that the trans isomer predominates at equilibrium.Identify the major products in the reaction of (R)-2-brimopentane with sodium cyanide in DMSO1. The ketone 2-heptanone has been identified as contributing to the odor of a number of dairy products, including condensed milk and cheddar cheese. Describe the synthesis of 2-heptanone from acetylene and any necessary organic and inorganic reagents. 2. Compound A has the molecular formula C14H25Br and was obtained by reaction of sodium acetylide (HC≡CNa) )with 1,12-dibromododecane. On treatment of compound A with sodium amide, it was converted to compound B (C14H24). Ozonolysis of compound B gave the diacid HO2C(CH2)12CO2H. Catalytic hydrogenation of compound B over Lindlar palladium gave compound C (C14H26), while hydrogenation over platinum gave compound D (C14H28). Sodium-ammonia reduction of compound B gave compound E (C14H26). Both C and E yielded O═CH(CH2)12CH═O on ozonolysis. Assign structures to compound A through E so as to be consistent with the observed transformations.
- From what you have learned about enols and the hydration of alkynes, predict what product is formed by the acid-catalyzed hydration of CH3CH2CH2C = COCH3. Draw a stepwise mechanism that illustrates how it is formed.(a) Explain the mechanism of a nucleophilic attack on the carbonyl group of an aldehyde or a ketone.(b) An organic compound (A) (molecular formula CgH16Q2) was hydrolysed with dilute sulphuric acid to give a carboxylic acid (B) and an alcohol (C). Oxidation of (C) with chromic acid also produced (B). On dehydration (C) gives but-1-ene. Write the equations for the reactions involved.When (ft)-6-bromo-2,6-dimethylnonane is dissolved in CH3OH, nucleophilic substitution yields an optically inactive solution. When the isomeric halide (fl)-2-bromo-2,5- dimethylnonane is dissolved in CH3OH under the same conditions, nucleophilic substitution forms an optically active solution. Draw the products formed in each reaction, and explain why the difference in optical activity is observed.