Organic Chemistry (6th Edition)
6th Edition
ISBN: 9781260119107
Author: Janice Gorzynski Smith
Publisher: McGraw Hill Education
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Chapter 12.9, Problem 17P
Interpretation Introduction
Interpretation: The products formed when both
Concept introduction: Addition of two hydroxyl groups on double bond to form
Stereospecific reactions are those in which the stereochemistry of the reactant controls the stereochemistry of the product.
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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 stereospecic.
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 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.
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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- 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_forwardIf the reaction of an alcohol with PBr3 follows an SN2 mechanism, what is the stereochemistry of the alkyl bromide formed from (R)-butan-2-ol?arrow_forwardDraw the substitution product formed when cis-1-bromo-4-methylcyclohexane and hydroxide ion undergo an SN2 reaction.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_forwardDraw the products (including stereoisomers) formed when 2- methylhex-2-ene is treated with HBr in the presence of peroxides.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
- Ignoring E and Z isomers, what 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_forwardDraw the major product formed when HBr reacts with the following epoxide. Use wedge/dash bonds, including H's at each stereogenic center, to show the stereochemistry of the product.arrow_forwardDraw the constitutional isomer formed when the following alkenes are treated with each set of reagents: [1] H2O, H2SO4; or [2] BH3 followed by H2O2, −OH.arrow_forward
- If 1-bromopentane is heated in acetone containing NaOH, what is the alkane produced? Draw and explain the step-by-step mechanism of the production of the compoundarrow_forwardWhat is the major product formed when 3-methyl-1-butene is treated with Hg(C2H3O2)2 in a THF/ethanol mixture followed by NaBH4 in base?arrow_forwardDraw 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_forward
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