ORGANIC CHEMISTRY-ACCESS
6th Edition
ISBN: 9781260475586
Author: SMITH
Publisher: MCG
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Chapter 12.3, Problem 5P
Interpretation Introduction
Interpretation: The reason as to why heats of hydrogenation cannot be used to determine the relative stability of
Concept introduction: Hydrogenation reaction is exothermic in nature due to the fact that the bonds are stronger in product than in reactant. Heat of hydrogenation can be used as measure for relative stability of
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A benzene ring alters the reactivity of a neighboring group in the so-called “benzylic” position, similarly to how a double bond alters the reactivity of groups in the “allylic” position. Benzylic cations, anions, and radicals are all more stable than simple alkyl intermediates. a) Use resonance structures to show the delocalization of the positive charge, negative charge, and unpaired electron of the benzyl cation, anion, and radical.
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Chapter 12 Solutions
ORGANIC CHEMISTRY-ACCESS
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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- Following are structural formulas and heats of combustion of acetaldehyde and ethylene oxide. Which of these compounds is more stable? Explain.arrow_forwardDraw the alkene that would react with the reagent given to account for the product formed. CH3 HCI CH3 CHCCH, ? + Či CH3 You do not have to consider stereochemistry. • You do not have to explicitly draw H atoms. • In cases where there is more than one answer, just draw one.arrow_forwardHow process of ring-flipping also affects the orientation of cyclohexane's hydrogen atoms ?arrow_forward
- Chlordane, like DDT, is an alkyl halide that was used as an insecticide for crops such as corn and citrus and for lawns. In 1983, it was banned for all uses except against termites, and in 1988, it was banned for use against termites as well. Chlordane can be synthesized from two reactants in one step. One of the reactants is hexachlorocyclopentadiene. What is the other reactant?arrow_forwardDraw the structure of the following compounds. Use line-angle structural formula. 1-bromo-4-ethyl-5- methylcyclohexane 3,7-dimethyl-5-propylnonae 5-chloro-1- ethylspiro[2.5]octane 2-bromo-4- methylbicyclo[3.2.1]octane * 5-cyclobutyl-2-cyclopropyl- 6,8-diethyl-3,7,7- trimethyldecane *arrow_forwardexplain and answer the "why" please. also, what makes one axial and the other equatorial? and what does Keq have to do with it ?arrow_forward
- explain and answer the "why" please. also, what makes one axial and the other equatorial? and what does Keq have to do with it ?arrow_forward2-methyl-2-hexanol was prepared by reacting an alkene with either hydroboration- oxidation or oxymercuration-reduction. Draw the structure of the alkene that was used to prepare the alcohol in highest yield. You do not have to consider stereochemistry. • Indicate the method of preparation by drawing either BH3 (for hydroboration- oxidation), or Hg (for oxymercuration-reduction), in a separate sketcher. • If there is more than one alkene that can be used for a given method, draw all of them. • If either hydroboration-oxidation or oxymercuration-reduction can be used, just give the structures for one method. Separate structures with + signs from the drop-down menu. ? ChemDoodleⓇ ⒸO [F ▼ [ ] در >arrow_forwardTwo substitution products result from the reaction between 3-chloro-3-methyl-1- butene with sodium acetate (CH3COO – Na +) in acetic acid under SN1. Identify the products.arrow_forward
- 2. Draw structures for the following systems. If more than one isomer is possible, draw strcutures for all the possible isomers. Benzene ring with a methyl group and a nitro group (Draw all possible isomers, and name them) Benzene ring connected to a heptane chain (Draw all possible isomers, and name them) 2-benzyl-3- methylbutan-1-olarrow_forward10) For the reaction between isopropyl 1-propyl (or 'n-propyl') ether and HBr, which type of reaction best matches the expected products? A) Acid-catalyzed dehydration B) Nucleophilic substitution reaction C) Ether cleavage reaction D) Nucleophilic addition-elimination reactionarrow_forwardThe compound below is treated with chlorine in the presence of light. CH3 CH3 CH3 Draw the structure for the organic radical species produced by reaction of the compound with a chlorine atom. Assume reaction occurs at the weakest C-H bond. • You do not have to consider stereochemistry. • You do not have to explicitly draw H atoms. Sn [F ?arrow_forward
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