Organic Chemistry - Standalone book
10th Edition
ISBN: 9780073511214
Author: Francis A Carey Dr., Robert M. Giuliano
Publisher: McGraw-Hill Education
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Chapter 6, Problem 33P
Write an equation, clearly showing the stereochemistry of the starting material and the product, for the reaction of
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The following compounds are given to you:2-Bromopentane, 2-Bromo-2-methylbutane, 1-Bromopentane(i) Write the compound which is most reactive towards SN2 reaction.(ii) Write the compound which is optically active.(iii) Write the compound which is most reactive towards P-elimination reaction.
Elimination of HBr from 2-bromobutane affords a mixture of 1-butene and 2-butene. With sodium ethoxide as base, 2-butene
constitutes 81% of the alkene products, but with potassium tert-butoxide, 2-butene constitutes only 67% of the alkene
products. Offer an explanation for this difference.
Predict-the-Product. Draw the structure(s) of the major organic product(s) formed in the following reactions. Please indicate stereochemistry if appropriate
Chapter 6 Solutions
Organic Chemistry - Standalone book
Ch. 6.1 - Prob. 1PCh. 6.2 - 1-Bromo-3-chloropropane reacts with one molar...Ch. 6.3 - Prob. 3PCh. 6.3 - The Fischer projection for (+)-2-bromooctane is...Ch. 6.3 - Would you expect the 2-octanol formed by SN2...Ch. 6.3 - Prob. 6PCh. 6.4 - Prob. 7PCh. 6.4 - The first step in the synthesis of the...Ch. 6.6 - Prob. 9PCh. 6.6 - Prob. 10P
Ch. 6.7 - Prob. 11PCh. 6.8 - Prob. 12PCh. 6.9 - Diethyl ether (CH3CH2OCH2CH3) has a dielectric...Ch. 6.9 - Unlike protic solvent which solvate from complexes...Ch. 6.10 - Prob. 15PCh. 6.10 - Prob. 16PCh. 6.10 - The hydrolysis of sulfonate of 2-octanol is...Ch. 6.11 - Prob. 18PCh. 6 - Prob. 19PCh. 6 - Prob. 20PCh. 6 - Both of the following reactions involve...Ch. 6 - Prob. 22PCh. 6 - Prob. 23PCh. 6 - Sodium nitrite (NaNO2) reacted with 2-iodooctane...Ch. 6 - Prob. 25PCh. 6 - Prob. 26PCh. 6 - Prob. 27PCh. 6 - The reaction of 2,2-dimethyl-1-propanol with HBr...Ch. 6 - If the temperature is not kept below 25oC during...Ch. 6 - The reaction of cyclopentyl bromide with sodium...Ch. 6 - Prob. 31PCh. 6 - Prob. 32PCh. 6 - Write an equation, clearly showing the...Ch. 6 - Prob. 34PCh. 6 - Based on what we know about nucleophiles and...Ch. 6 - Prob. 36PCh. 6 - Prob. 37PCh. 6 - Prob. 38PCh. 6 - Prob. 39PCh. 6 - Prob. 40PCh. 6 - Prob. 41DSPCh. 6 - Prob. 42DSPCh. 6 - Prob. 43DSPCh. 6 - Prob. 44DSPCh. 6 - Prob. 45DSPCh. 6 - Prob. 46DSP
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- Draw the structural formulas for the first two intermediates formed in the hydrolysis of (1R,2S)-1,2-epoxy-1-methylcyclopentane with aqueous acid. Show stereochemistry if product is a meso compound.arrow_forwardFollowing compounds are given to you:2-Bromopentane, 2-Bromo-2-methylbutane, 1-Bromopentane(i) Write the compound which is most reactive towards SN2 reaction.(ii) Write the compound which is optically active.(iii) Write the compound which is most reactive towards β – elimination reactionarrow_forwardUsing skeletal formulas and where appropriate showing the correct stereochemistry and bond geometry draw the structures of the following compounds oct-6-under-3-one (Z)-3-bromo-5-methylhept-3-ene (R) -3-iodbutanoic acidarrow_forward
- When 2-bromo-2-methylbutane is treated with a base, a mixture of 2-methyl-2-butene and 2-methyl-1- butene is produced. When potassium hydroxide is the base, 2-methyl-1-butene accounts for 45% of the product mixture. However, when potassium tert-butoxide is the base, 2-methyl-1-butene accounts for 70% of the product mixture. What percent of 2-methyl-1-butene would be in the mixture if potassium propoxide were the base? base Br A. Less than 45% B. C. 45% Between 45% and 70% D. More than 70%arrow_forwardList the alkenes that would be formed when 2-bromo-3-methylbutane is subjected to dehydrohalogenation with potassium ethoxide in ethanol and predict which one is the major product.arrow_forwardDraw the structures, including stereochemistry, of the major products (A) from the re- action between 1-pentene and mercury(II) acetate in methanol. Assign the configura- tions (R or S) of any stereocenters. Draw the structures, including stereochemistry, of the products (B) obtained from demercuration of A with sodium borohydride (NaBH4); assign the configurations of the stereocenters. Hg(OAc)₂ CH₂OH A NaB H₁ H₂O, EtOH Barrow_forward
- Write an equation(s) to illustrate the mechanism for the dehydrohalogenation of 2-bromo-2-methylbutane. Give the major product expected from the mechanism and use arrows to indicate electron flow. Why is this reaction referred to as a concerted process?arrow_forwardwhy do (R)-3-chloro-1-methylcycloprop-1-ene and 5-Bromo-1,3-Cyclohexadiene react differently with cyanide (why doesn't cyanide pass through its usual mechanism for these two products and what did you obtain these specific products)arrow_forward(c) Alkenes can be transformed into epoxides by an epoxidation reaction. If the following hexenes are all subjected to an epoxidation reaction, which one would give an achiral epoxide? Explain your answer. 1-hexene cis-2-hexene trans-2-hexene cis-3-hexene trans-3-hexenearrow_forward
- Provide the systematic name for each of the following isomeric esters with the chemical formula C-H₁2O₂. (Be sure to indicate double bond stereochemistry using (E)/(Z) notation. Indicate stereochemistry in rings with the terms cis or trans. It is not necessary to use italics in writing compound names.) ball & stick - + labels ball & stick- + labels ball & stick + labels 12arrow_forwardDraw the product(s) obtained when benzoquinone is treated with excess butadiene. Using wedges and dashes, indicate the stereochemistry.arrow_forwardWhich alkene would give a single compound (not a mixture of enantiomers and/or diastereomers) as the major organic product upon reaction with HBr in the presence of peroxide and light?arrow_forward
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