Organic Chemistry
4th Edition
ISBN: 9780077479824
Author: SMITH, Janice Gorzynski/
Publisher: McGraw-Hill College
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Chapter 12, Problem 12.79P
Interpretation Introduction
Interpretation: Dihydroxylation occurs by syn or anti addition, is to be determined using the given method.
Concept introduction: In presence of peroxide,
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Draw the product or products that will be obtained from the reaction of cis-2-butene and trans-2-butene with each of the following reagents. If a product can exist as stereoisomers, show which stereoisomers are formed.
1. HCl. 4.Br2 in CH2Cl2 7. H2O + H2SO4
2. BH3/THF, followed by HO-, H2O2, H2O 5. Br2 + H2O 8. CH3OH + H2SO4 3. a peroxyacid 6. H2 + Pd/C
1. Predict the elimination products of the following reactions. When two alkenes are possible, predict which one will be the major product. Explain your answers, showing the degree of substitution of each double bond in the products. 2. Which of these reactions are likely to produce both elimination and substitution products?
(a) 2-bromopentane +NaOCH3
(b) 3-bromo-3-methylpentane +NaOMe(Me= methyl, CH3)
(c) 2-bromo-3-ethylpentane +NaOH
(d) cis-1-bromo-2-methylcyclohexane +NaOEt (Et= ethyl, CH2CH3)
name and draw the product/s formed from the reaction of 3-methylpent-2-ene:
1. with HBr
2. with Cl2
3. H2O in the presence of H2SO4
4. ethanol in the presence of H2SO4
5. Br2, H2O
6. [1] 9-BBN; [2] H2O2, OH-
Chapter 12 Solutions
Organic Chemistry
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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- A chemist allows some pure (2S,3R)-3-bromo-2,3-diphenylpentane to react with a solution of sodium ethoxide(NaOCH2 CH3) in ethanol. The products are two alkenes: A (cis-trans mixture) and B, a single pure isomer. Under the same conditions, the reaction of (2S,3S)-3-bromo-2,3-diphenylpentane gives two alkenes, A (cis-trans mixture) and C. Upon catalytic hydrogenation, all three of these alkenes (A, B, and C) give 2,3-diphenylpentane. Determine the structures of A, B, and C; give equations for their formation; and explain the stereospecificity of these reactions.arrow_forwardWhen 2-pentene is treated with Cl2 in methanol, three products are formed. Account for the formation of each product (you need not explain their relative percentages).arrow_forwardConsider 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_forward
- Alkenes can be hydrated to form alcohols by (1) hydroboration followed by oxidation with alkaline hydrogen peroxide and (2) acid-catalyzed hydration. Compare the product formed from each alkene by sequence (1) with those formed from (2). Q.)1-Methylcyclohexenearrow_forward1-pentyne reacts with dicylohexylborane, followed by oxidation, to produce pentanal. The organoborane formed in step 1 is oxidized by H2O2 in the presence of OH– in the next step of the reaction. Which of the following options correctly describe this process? Choose one or more: A. –BR2 acts as a leaving group in this step. B. OH– must attack from the face of the alkene opposite the –BR2 group. C. OH replaces –BR2 in this step. D. OH replaces H in this step. E. Configuration at the carbon-bearing B is retained in the reaction.arrow_forwardA chemist allows some pure (2S,3R)-3-bromo-2,3-diphenylpentane to react with a solution of sodium ethoxide(NaOCH2CH3) in ethanol. The products are two alkenes: A (cis-trans mixture) and B, a single pure isomer. Under thesame conditions, the reaction of (2S,3S)-3-bromo-2,3-diphenylpentane gives two alkenes, A (cis-trans mixture) and C.Upon catalytic hydrogenation, all three of these alkenes (A, B, and C) give 2,3-diphenylpentane. Determine the structuresof A, B, and C; give equations for their formation; and explain the stereospecificity of these reactionsarrow_forward
- Identify two alkenes that react with HBr to form 1-bromo-1-methylcyclohexane without undergoing a carbocation rearrangement.arrow_forwardAlkenes can be hydrated to form alcohols by (1) hydroboration followed by oxidation with alkaline hydrogen peroxide and (2) acid-catalyzed hydration. Compare the product formed from each alkene by sequence (1) with those formed from (2). Q.)Cyclopentenearrow_forwardThe reaction of propan-2-ol in the following series of reactions will yield __________. 1) NaH; then set aside until Step 3; 2) CH4 plus Br2, light and heat, assume monobromination; 3) the product of Step 1 mixed with the product of Step 2 an alkene an alkoxide an acetylide an ether an alkyl bromidearrow_forward
- (1) Predict the outcome of the addition of HBr to (a) trans-2-pentene, (b) 2-methyl-2-butene, and (c) 4-methylcyclohexene. How many isomers can be formed in each case? (2) Addition of HBr to 3,3-dimethyl-1-butene gives a mixture of two isomeric alkyl bromide products. Draw structures for the two products, and give a mechanistic explanation for their formation.arrow_forwardWhat are the reagents used to convert 2-butyne to C4H8? What are the products when that C4H8 is mixed with OsO4, and H2O (the formula will be C4H10O2 racemic)? What is the product when C4H8 is mixed with RCO3H, and H2O (the formula will be C4H10O2 meso)?arrow_forwardIn each case below select the synthetic procedure/s that could be used to carry out the transformation, giving the alcohol shown as the single major product.The procedures are:Hydroboration/oxidation: alkene + BH3; then H2O2, -OH.Oxymercuration: alkene + Hg(OAc)2, H2O; then NaBH4arrow_forward
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