ORGANIC CHEMISTRY
6th Edition
ISBN: 9781266633973
Author: SMITH
Publisher: MCG
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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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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.
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.
Chapter 12 Solutions
ORGANIC CHEMISTRY
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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- A 2-bromobutane react with methanol and form a enantiomeric pair of 2-methoxybutane. Draw the structures of the enntiomeric pairs of ethers.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 the product formed when CH3CH2C=CH is treated with each of the following sets of reagents: (a) H2O, H2SO4, HgSO4; and (b) R2BH, followed by H2O2, HO−.arrow_forward
- Draw the alkene structure that produced the following compounds in a ozonolysis reaction as specified. 8.4 H C7H12 1.03 2. (CH3)2S Harrow_forwardDraw all possible products formed when 2-methylbut-2-ene undergoes addition with HCl. Label them as being either the major or the minor product.arrow_forwardLess stable alkenes can be isomerized to more stable alkenes by treatment with strong acid. For example, 2,3- dimethylbut-1-ene is converted to 2,3-dimethylbut-2-ene when treated with H2SO4. Draw a stepwise mechanism for this isomerization process.arrow_forward
- 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_forwardIdentify two alkenes that react with HBr to form 1-bromo-1-methylcyclohexane without undergoing a carbocation rearrangement.arrow_forwardМСРВА Alkenes are oxidized to give epoxides on treatment with a peroxyacid, RCO3H, such as metachloroperoxybenzoic acid (MCPBA). Peroxyacids transfer an oxygen atom to the alkene with syn stereochemistry, i.e. both C-O bonds form on the same face of the double bond, through a single step mechanism without intermediates. The oxygen atom farthest from the carbonyl group is the one transferred. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions H .CI .CI HOarrow_forward
- Draw the alkene reactant of the following reaction. n 6 H3o+ H3C OH H20arrow_forwardIgnoring 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_forwardWhich represents an efficient synthetic route to go from an alkane to an alkene? O elimination with NaNH2, followed by a water workup O anti-Markovnikov hydrohalogenation, followed by elimination O radical bromination, followed by elimination O hydration, followed by elimination O hydration, followed by ozonolysis of the double bondarrow_forward
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