Organic Chemistry-Package(Custom)
4th Edition
ISBN: 9781259141089
Author: SMITH
Publisher: MCG
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Textbook Question
Chapter 12, Problem 12.18P
Draw the products formed when both cis- and trans-but-2-ene are treated with
followed by hydrolysis with
syn dihydroxylation is stereospecific.
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Draw the products formed when both cis- and trans-but-2-ene are treated with a peroxyacid followed by -OH (in H2O).Explain how these reactions illustrate that anti dihydroxylation is stereospecic.
Draw the products formed when the following alkynes are treated with each set of reagents: [1] H2O, H2SO4, HgSO4; or [2] R2BH followed by H2O2, −OH.
Draw all of the substitution and elimination products formed from the given alkyl halide with each reagent: (a) CH3OH; (b) KOH. Indicate the stereochemistry around the stereogenic centers present in the products, as well as the mechanism by which each product is formed.
Chapter 12 Solutions
Organic Chemistry-Package(Custom)
Ch. 12 - Prob. 12.1PCh. 12 - Prob. 12.2PCh. 12 - Prob. 12.3PCh. 12 - Prob. 12.4PCh. 12 - Prob. 12.5PCh. 12 - Given that syn addition of H2 occurs from both...Ch. 12 - Compound Molecular formula before...Ch. 12 - Draw the products formed when triacylglycerol A is...Ch. 12 - Prob. 12.9PCh. 12 - Prob. 12.10P
Ch. 12 - Problem 12.11 (a) Draw the structure of a compound...Ch. 12 - Prob. 12.12PCh. 12 - Prob. 12.13PCh. 12 - Prob. 12.14PCh. 12 - Prob. 12.15PCh. 12 - Prob. 12.16PCh. 12 - Prob. 12.17PCh. 12 - Problem 12.18 Draw the products formed when both...Ch. 12 - Prob. 12.19PCh. 12 - Prob. 12.20PCh. 12 - Prob. 12.21PCh. 12 - Prob. 12.22PCh. 12 - Prob. 12.23PCh. 12 - Problem 12.24 Draw the organic products in each of...Ch. 12 - Prob. 12.25PCh. 12 - Prob. 12.26PCh. 12 - Problem 12.27 Draw the products of each Sharpless...Ch. 12 - Prob. 12.28PCh. 12 - 12.29 Draw the products formed when A is treated...Ch. 12 - Prob. 12.30PCh. 12 - 12.31 Devise a synthesis of the following compound...Ch. 12 - Label each reaction as oxidation, reduction, or...Ch. 12 - Prob. 12.33PCh. 12 - Prob. 12.34PCh. 12 - Prob. 12.35PCh. 12 - Prob. 12.36PCh. 12 - 12.37 Stearidonic acid (C18H28O2) is an...Ch. 12 - Draw the organic products formed when cyclopentene...Ch. 12 - Prob. 12.39PCh. 12 - Draw the organic products formed when allylic...Ch. 12 - Draw the organic products formed in each reaction...Ch. 12 - Draw the organic products formed in each reaction....Ch. 12 - Prob. 12.43PCh. 12 - Prob. 12.44PCh. 12 - Prob. 12.45PCh. 12 - What alkene is needed to synthesize each 1,2-diol...Ch. 12 - Prob. 12.47PCh. 12 - Draw the products formed after Steps 1 and 2 in...Ch. 12 - Prob. 12.49PCh. 12 - Prob. 12.50PCh. 12 - Prob. 12.51PCh. 12 - What alkyne gives each set of products after...Ch. 12 - Prob. 12.53PCh. 12 - Prob. 12.54PCh. 12 - Prob. 12.55PCh. 12 - 12.54 An unknown compound A of molecular formula ...Ch. 12 - 12.55 DHA is a fatty acid derived from fish oil...Ch. 12 - Prob. 12.58PCh. 12 - Prob. 12.59PCh. 12 - 12.58 Epoxidation of the following allylic alcohol...Ch. 12 - What allylic alcohol and DET isomer are needed to...Ch. 12 - Devise a synthesis of each hydrocarbon from...Ch. 12 - Prob. 12.63PCh. 12 - 12.62 It is sometimes necessary to isomerize a cis...Ch. 12 - Prob. 12.65PCh. 12 - Prob. 12.66PCh. 12 - Prob. 12.67PCh. 12 - Prob. 12.68PCh. 12 - Devise a synthesis of each compound from the...Ch. 12 - Devise a synthesis of each compound from acetylene...Ch. 12 - Prob. 12.71PCh. 12 - Prob. 12.72PCh. 12 - Prob. 12.73PCh. 12 - Prob. 12.74PCh. 12 - Prob. 12.75PCh. 12 - Prob. 12.76PCh. 12 - 12.72 Draw a stepwise mechanism for the following...Ch. 12 - Prob. 12.78PCh. 12 - Prob. 12.79PCh. 12 - Prob. 12.80PCh. 12 - 12.75 Sharpless epoxidation of allylic alcohol X...
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- Draw the organic products formed when cyclopentene is treated withfollowing reagent. [1] CH3CO3H; [2] H2O, HO−arrow_forwardWhat two enols are formed when pent-2-yne is treated with H2O, H2SO4, and HgSO4? Draw the ketones formed from these enols after tautomerization.arrow_forwardA 2-bromobutane react with methanol and form a enantiomeric pair of 2-methoxybutane. Draw the structures of the enntiomeric pairs of ethers.arrow_forward
- 4. What are the products obtained from the following elimination reaction? Indicate the major product. CH;CH2CCH3 H2O CI 5. a) Determine the major product that is formed when the alkyl halide reacts with a hydroxide ion in an elimination reaction. CH;CH,CH,CH,CCH3 Br b) For the major elimination product obtained in 5a), which stereoisomer (cis or trans) is obtained in greater yield? Draw the two isomers and provide the names of the compounds.arrow_forwardReaction of 2-methylpropene with CH3OH in the presence of H2SO4 catalyst yieldsmethyl tert-butyl ether, CH3OC(CH3)3, by a mechanism analogous to that of acid- catalyzed alkene hydration. Write the mechanism, using curved arrows for each step.arrow_forwardDraw all of the substitution and elimination products formed from thegiven alkyl halide with each reagent: (a) CH3OH; (b) KOH. Indicate thestereochemistry around the stereogenic centers present in the products,as well as the mechanism by which each product is formed.arrow_forward
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- Draw the constitutional isomer formed when the attached alkenes are treated with each set of reagents: [1] H2O, H2SO4; or [2] BH3 followed by H2O2, −OH.arrow_forwardHh.183.arrow_forwardWhen 2-pentene is treated with Cl, in methanol, three products are formed. Account for the formation of each product (you need not explain their relative percentages). CI OCH3 H,CO CI CI CI Cle CH;CHCHCH,CH, + CH;CHCHCH,CH3 + CH,CHČHCH,CH, CH;OH CH;CH=CHCH,CH, 50% 35% 15%arrow_forward
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