Organic Chemistry - Standalone book
10th Edition
ISBN: 9780073511214
Author: Francis A Carey Dr., Robert M. Giuliano
Publisher: McGraw-Hill Education
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Textbook Question
Chapter 12.15, Problem 16P
The regioselectivity of Birch reduction of alkoxy-substituted benzenes is the same as for
alkylbenzenes. What did Arthur Birch isolate when he carried out the following reaction?
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Chapter 12 Solutions
Organic Chemistry - Standalone book
Ch. 12.2 - Write structural formulas for toluene (C6H5CH3)...Ch. 12.3 - Prob. 2PCh. 12.5 - Prob. 3PCh. 12.5 - Prob. 4PCh. 12.6 - Prob. 5PCh. 12.6 - Chrysene is an aromatic hydrocarbon found in coal...Ch. 12.8 - Prob. 7PCh. 12.9 - As measured by their first-order rate constants,...Ch. 12.9 - Give the structure of the principal organic...Ch. 12.9 - Prob. 10P
Ch. 12.10 - Prob. 11PCh. 12.11 - Prob. 12PCh. 12.12 - Prob. 13PCh. 12.13 - Prob. 14PCh. 12.13 - Prob. 15PCh. 12.15 - The regioselectivity of Birch reduction of...Ch. 12.16 - Prob. 17PCh. 12.17 - Both cyclooctatetraene and styrene have the...Ch. 12.17 - Prob. 19PCh. 12.18 - Give an explanation for each of the following...Ch. 12.19 - Prob. 21PCh. 12.19 - What does a comparison of the heats of combustion...Ch. 12.20 - Prob. 23PCh. 12.20 - Prob. 24PCh. 12.20 - Prob. 25PCh. 12.20 - Prob. 26PCh. 12.20 - Prob. 27PCh. 12.20 - Prob. 28PCh. 12.21 - Prob. 29PCh. 12.21 - Prob. 30PCh. 12.22 - Prob. 31PCh. 12.22 - Prob. 32PCh. 12 - Write structural formulas and give the IUPAC names...Ch. 12 - Prob. 34PCh. 12 - Prob. 35PCh. 12 - Prob. 36PCh. 12 - Prob. 37PCh. 12 - Acridine is a heterocyclic aromatic compound...Ch. 12 - Prob. 39PCh. 12 - Prob. 40PCh. 12 - Prob. 41PCh. 12 - Evaluate each of the following processes applied...Ch. 12 - Prob. 43PCh. 12 - Prob. 44PCh. 12 - Prob. 45PCh. 12 - Prob. 46PCh. 12 - Anthracene undergoes a DielsAlder reaction with...Ch. 12 - Prob. 48PCh. 12 - Prob. 49PCh. 12 - The relative rates of reaction of ethane, toluene,...Ch. 12 - Both 1,2-dihydronaphthalene and...Ch. 12 - Prob. 52PCh. 12 - Prob. 53PCh. 12 - Prob. 54PCh. 12 - Prob. 55PCh. 12 - Prob. 56PCh. 12 - Each of the following reactions has been described...Ch. 12 - Prob. 58PCh. 12 - A compound was obtained from a natural product and...Ch. 12 - Prob. 60PCh. 12 - Suggest reagents suitable for carrying out each of...Ch. 12 - Prob. 62PCh. 12 - Prob. 63DSPCh. 12 - Prob. 64DSPCh. 12 - Prob. 65DSPCh. 12 - Prob. 66DSP
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- Elimination of HBr from 2-bromobutane affords a mixture of but-1-ene and but-2-ene. With sodium ethoxide as base, but2-ene constitutes 81% of the alkene products, but with potassium tert-butoxide, but-2-ene constitutes only 67% of the alkene products. Offer an explanation for this difference.arrow_forwardExplain the Limitations on Electrophilic Substitution Reactions with Substituted Benzenes ?arrow_forwardX Upon ozonolysis, Compound X produces two compounds: Compound Y and Compound Z. Compound Y can also be prepared from the following synthetic route: PCC 1. R₂BH, THF 1. Mg. Et₂O PCC Compound Y 2. CH₂Cl₂ 2. NaOH, HO CH₂Cl₂ 3. H₂O* From this information, draw the structures of Compounds X, Y, and Z. For Compounds X and Z, different substituents are possible. For grading purposes, just use hydrogens as the substituents. Br مرد →] ►arrow_forward
- 2-Methylhex-3-yne can be prepared by the reaction of an alkynide with an alkyl halide. Does the better synthesis involve alkynide attack on bromoethane or on 2-bromopropane? Explain your reasoning.arrow_forwardWhat is the structural requirement for a substance to react with ammoniacal AgNO3? Why would acetylene react with Tollen's reagent but not cyclohexane or cyclohexene?arrow_forwardAlkyl halides undergo elimination reactions to produce alkenes by the reacting with strong bases as shown in the following reaction (see image). In general, compounds where the halogen is axial (axial position) are much more reactive than those in which they are in the equatorial position. Taking the above into account: a. Which of the following compounds would give a faster elimination reaction: cis-1-bromo-2-tert-butylcyclohexane or trans-1-bromo-2-tert-butylcyclohexane? Draw the corresponding structures and clearly explain the choice.arrow_forward
- Which one of the following alkenes is the Zaitsev product formed by the reaction of hydroxide with 3-bromo-2,3-dimethylpentane?arrow_forwardOne compound that contributes to the “seashore smell” at beaches in Hawai‘i is dictyopterene D', a component of a brown edible seaweed called limu lipoa. Hydrogenation of dictyopterene D' with excess H2 in the presence of a Pd catalyst forms butylcycloheptane. Ozonolysis with O3 followed by (CH3)2S forms CH2(CHO)2, HCOCH2CH(CHO)2, and CH3CH2CHO. What are possible structures of dictyopterene D'?arrow_forwardWittig reactions with the following -chloroethers can be used for the synthesis of aldehydes and ketones. (a) Draw the structure of the triphenylphosphonium salt and Wittig reagent formed from each chloroether. (b) Draw the structural formula of the product formed by treating each Wittig reagent with cyclopentanone. Note that the functional group is an enol ether or, alternatively, a vinyl ether. (c) Draw the structural formula of the product formed on acid-catalyzed hydrolysis of each enol ether from part (b).arrow_forward
- What hydrocarbon forms the following products after reaction first with ozone and then with dimethyl sulfide?arrow_forwardDraw the organic products formed when cyclopentene is treated with each reagent. With some reagents, no reaction occurs. a.H2 + Pd-C b.H2 + Lindlar catalyst c.Na, NH3 d.CH3CO3H e.[1] CH3CO3H; [2] H2O, HO− f.[1]OsO4 + NMO; [2] NaHSO3, H2O g.KMnO4, H2O, HO− h.[1] LiAlH4; [2] H2O i. [1] O3; [2] CH3SCH3 j.(CH3)3COOH, Ti[OCH(CH3)2]4, (−)-DET k.mCPBA l.Product in (k); then [1] LiAlH4; [2] H2Oarrow_forwardCH3 CH3 1. ВНз, THF 2. NaOH, H2O, H2О2 H3C FCH2 HO H3C Alkenes can be hydrated via the addition of borane to yield alcohols with non-Markovnikov regiochemistry. The boron atom is an electrophile and thus follows Markovnikov's rule in adding to the carbon containing the most hydrogens. Oxidation of the alkylborane with basic peroxide yields the product alcohol. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions R ö-OH R-B-0-OH R-B Rarrow_forward
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