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(a)
Interpretation: The reason corresponding to the fact that the single kekule structure is consistent with the first result, but does not explain the second result is to be stated.
Concept introduction: Kekule structure of benzene consists of three alternating double and single bonds. But his structures do not take into the account of resonance structures of benzene.
(b)
Interpretation: The reason corresponding to the fact that resonance description of benzene is consistent with results of both reactions is to be stated.
Concept introduction: Kekule structure of benzene consists of three alternating double and single bonds. But his structures do not consider the resonance structures of benzene.
Most of the organic structures cannot be represented using single Lewis structure. Therefore, there exists more than one Lewis structure for representing a molecule or ion. These structures are known as resonance structures. These resonance structure combine together to give resonance hybrid that is lower in energy and is the most stable structure.
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Chapter 17 Solutions
Package: Loose Leaf for Organic Chemistry with Biological Topics with Connect Access Card
- Jj.149.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_forwardUsing the Functional Group and Reagent to Identity the Type of Reaction Draw the product of each reaction.arrow_forward
- Draw the structure of the organic product or products formed in the reaction. H₂C HU IN. H HU of H₂ MgBr 1. H₂C A -CH₂ 2. H3O+ Select Draw / || III Rings C H Morearrow_forwardGive the structure corresponding to each IUPAC name. a. 2-bromobutanoic acid b. 2,3-dimethylpentanoic acid c. 3,3,4-trimethylheptanoic acid d. 2-sec-butyl-4,4-diethylnonanoic acid e. 3,4-diethylcyclohexanecarboxylic acid f. 1-isopropylcyclobutanecarboxylic acidarrow_forwardLocate the isoprene units in each compound.arrow_forward
- Instead of washing the product several times with water, we could neutralize the basic solution by washing with an acid such as HCI. What could happen to the product if this is done? Draw the structure of the alternate product that you could 1. isolate. NAOH CH + CH.CCH, -CH-CH-C-CH-CH H:0 dibenzalacetonearrow_forwardWhich of these statements is false regarding the following reaction? 1. LIAIH, 1. H* HO. ОН Select one: a. The reactant has a lower pKa than the product. b. The reagent can be synthesized in a reaction between an alcohol and an acid chloride. c. Product can react with SOCI2 to produce 1- chloropropane d. The carbon-oxygen bond in the product is longer than the carbon-oxygen bond of the carbonyl in the reactant.arrow_forwardSynthesize each compound from benzonitrile (C6H5CN) as the only organic starting material; that is, every carbon in the product must originate in benzonitrile.arrow_forward
- Draw the organic products formed when 4-octyne is treated with each reagent. a. H2 (excess) + Pd-C b. H2 + Lindlar catalyst c. Na, NH, d. [1] Ogi (2] H,0arrow_forwardInstructions: Draw out each compound to clearly show what groups are bonded to the carbonyl carbon. Label each compound as a carboxylic acid, ester, or amide. a. CH3CH2CO2CH2CH3 b. CH3CONHCH3 c. (CH3)3CCO2H d. (CH3)2CHCON(CH3)2 Instructions: Give the IUPAC name for each compound. A. CH₂ CH₂CH₂CH₂CCH₂COOH CH3 B. CH₂CHCH₂CH₂COOH CH₂COOH CH₂CH3 C. (CH,CH,),CHCH,CHCOOH Instructions: Give the structure corresponding to each IUPAC name. a. 2-bromobutanoic acid b. 2,3-dimethylpentanoic acid c. 2-ethyl-5,5-dimethyloctanoic acid d. 3,4,5,6-tetraethyldecanoic acidarrow_forwardIn the chemical synthesis of DNA and RNA, hydroxyl groups are normally converted to triphenylmethyl (trityl) ethers to protect the hydroxyl group from reaction with other reagents. Triphenylmethyl ethers are stable to aqueous base but are rapidly cleaved in aqueous acid. (a) Why are triphenylmethyl ethers so readily hydrolyzed by aqueous acid? (b) How might the structure of the triphenylmethyl group be modified to increase or decrease its acid sensitivity?arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
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