Organic Chemistry (6th Edition)
6th Edition
ISBN: 9781260119107
Author: Janice Gorzynski Smith
Publisher: McGraw Hill Education
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Textbook Question
Chapter 12.9, Problem 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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(a) Draw the products (including stereoisomers) formed when 2-methylhex-2-ene is treated with HBr in the presence of peroxides. (b) Draw the products (including stereoisomers) formed when (S)-2,4-dimethylhex-2-ene is treated with HBr and peroxides under similar conditions.
Draw the products formed when both cis- and trans-but-2-ene are treated with OsO4, followed by hydrolysis with NaHSO3 + H2O. Explain how these reactions illustrate that syn dihydroxylation is stereospecific.
Draw the products (including stereoisomers) formed when 2- methylhex-2-ene is treated with HBr in the presence of peroxides.
Chapter 12 Solutions
Organic Chemistry (6th Edition)
Ch. 12.1 - Prob. 1PCh. 12.3 - Problem 12.2 What alkane is formed when each...Ch. 12.3 - Prob. 3PCh. 12.3 - Prob. 4PCh. 12.3 - Prob. 5PCh. 12.3 - Prob. 6PCh. 12.3 - Compound Molecular formula before...Ch. 12.4 - Problem 12.8 Draw the products formed when...Ch. 12.5 - Prob. 9PCh. 12.5 - Prob. 10P
Ch. 12.5 - Problem 12.11 (a) Draw the structure of a compound...Ch. 12.5 - Prob. 12PCh. 12.5 - Prob. 13PCh. 12.6 - Problem 12.14 Draw the products of each...Ch. 12.8 - Prob. 15PCh. 12.8 - Problem 12.16 Draw all stereoisomers formed when...Ch. 12.9 - Prob. 17PCh. 12.9 - Problem 12.18 Draw the products formed when both...Ch. 12.10 - Problem 12.19 Draw the products formed when each...Ch. 12.10 - Prob. 20PCh. 12.10 - Prob. 21PCh. 12.11 - Problem 12.22 Draw the products formed when each...Ch. 12.11 - Prob. 23PCh. 12.12 - Problem 12.24 Draw the organic products in each of...Ch. 12.13 - Prob. 25PCh. 12 - 12.29 Draw the products formed when A is treated...Ch. 12 - Prob. 30PCh. 12 - Prob. 31PCh. 12 - Prob. 32PCh. 12 - Prob. 33PCh. 12 - Draw the organic products formed when cyclopentene...Ch. 12 - Draw the organic products formed when allylic...Ch. 12 - Prob. 39PCh. 12 - Prob. 40PCh. 12 - Prob. 41PCh. 12 - What alkene is needed to synthesize each 1,2-diol...Ch. 12 - 12.48 Draw the products formed in each oxidative...Ch. 12 - What alkene or alkyne yields each set of products...Ch. 12 - Prob. 47PCh. 12 - Prob. 48PCh. 12 - Prob. 49PCh. 12 - Prob. 50PCh. 12 - 12.57 Draw the product of each asymmetric...Ch. 12 - 12.60 Identify A in the following reaction...Ch. 12 - Prob. 58PCh. 12 - 12.62 It is sometimes necessary to isomerize a cis...Ch. 12 - 12.63 Devise a synthesis of each compound from...Ch. 12 - Prob. 61P
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- 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.arrow_forwardDraw 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.arrow_forwardDraw 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.arrow_forward
- 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_forward4. 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_forward
- Consider a reaction where cis-but-2-ene is treated with a peroxy acid followed by OH- /H20. Draw the structure of one product that is formed in the reaction, including correct stereochemistry.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_forwardDraw 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 stereospecific.arrow_forward
- Consider a reaction where cis-but-2-ene is treated with OsO4 followed by NaHSO3/H2O. Draw the structure of one product that is formed in the reaction, including correct stereochemistry.arrow_forwardWhen alkyne A is treated with NaNH2 followed by CH3I, a product havingmolecular formula C6H10O is formed, but it is not compound B. What isthe structure of the product, and why is it formed?arrow_forwardDraw the products formed when each alkene is treated with BH3 followed by H2O2,HO−. Include the stereochemistry at all stereogenic centers.arrow_forward
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