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(a)
Interpretation:
The given isomeric carbocations are to be classified as primary, secondary and tertiary and the most stable carbocation is to be predicted.
Concept introduction:
Carbocations are the reaction intermediates and they contain the electron deficient positively charged carbon atom. The electron deficient carbon is
(b)
Interpretation:
The given isomeric carbocations are to be classified as primary, secondary and tertiary and the most stable carbocation is to be predicted.
Concept introduction:
Carbocations are the reaction intermediates and they contain the electron deficient positively charged carbon atom. The electron deficient carbon is
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Chapter 4 Solutions
EBK ORGANIC CHEMISTRY
- Which of the following is true for the reactions of alkyl halides? (a) The characteristic reactions of alkyl halides are oxidation and reduction.(b) The characteristic reactions of alkyl halides are elimination and substitutionc. The characteristic reactions of alkyl halides are addition and substitutiond. Characteristic reactions of alkyl halides are addition and elimination.arrow_forwardFor each alkene, indicate the direction of the dipole moment. For each pair, determine which compound has the largerdipole moment.(a) cis-1,2-difluoroethene or trans-1,2-difluoroethene(b) cis-1,2-dibromoethene or trans-2,3-dibromobut-2-enearrow_forwardwhich one of the following cycloalkanes will be least stable? (a) cyclopropane (b) cyclobutane (c) cyclopentan (d) cyclohexanearrow_forward
- Consider 1-bromopropane, CH3CH2CH2Br. (a) Which of these is the lowest energy conformation?arrow_forwardExplain why (i) the dipole moment in chlorobenzene is lower than that of cyclohexyl chloride. (ii) haloalkanes are only slightly soluble in water but dissolve easily in organic solvents.arrow_forwardUsing cyclohexane as your starting material, show how you would synthesize each of the following compounds. (Onceyou have shown how to synthesize a compound, you may use it as the starting material in any later parts of this problem.)(a) bromocyclohexane (b) cyclohexenearrow_forward
- (a) One test for the presence of an alkene is to add a smallamount of bromine, which is a red-brown liquid, and lookfor the disappearance of the red-brown color. This test doesnot work for detecting the presence of an aromatic hydrocarbon.Explain. (b) Write a series of reactions leading topara-bromoethylbenzene, beginning with benzene andusing other reagents as needed. What isomeric side productsmight also be formed?arrow_forwardConsider 1-bromopropane, CH3CH2CH2Br. (a) Draw a Newman projection for the conformation in which CH3 and -Br are anti (dihedral angle 180°). (b) Draw Newman projections for the conformations in which - CH3 and -Br are gauche (dihedral angles 60° and 300°). (c) Which of these is the lowest energy conformation? (d) Which of these conformations, if any, are related by reflection?arrow_forward1. (a) Describe aromaticity, Kekule structure and resonance structure for benzene. (b) Why is benzene more stable than aliphatic alkenes?arrow_forward
- (a) Compound D undergoes a reaction with hydrogen bromide, HBr to produce 2-bromobutane. D exists as cis-trans isomers and decolourises bromine solution in methylene chloride, CH2CI2. (i) Draw and name the structure of compound D. (ii) Draw two (2) constitutional isomers of compound D.arrow_forwardAccording to IUPAC nomenclature rules, the naturally occurring form of menthol can also be called (1R, 2S, 5R)-2-isopropyl-5- methylcyclohexanol. (a) Draw the bond-line structure of the enantiomer of this compound, including wedged and hashed bonds where appropriate to show stereochemical configuration. (b) Draw the chair conformation of this structure and perform a ring flip operation. Circle the most stable chair conformer. Briefly explain why it is the most stable.arrow_forwardDisiamylborane adds only once to alkynes by virtue of its two bulky secondary isoamylgroups. Disiamylborane is prepared by the reaction of BH3 # THF with an alkene.(a) Draw the structural formulas of the reagents and the products in the preparation ofdisiamylborane.(b) Explain why the reaction in part (a) goes only as far as the dialkylborane. Why isSia3B not formed?arrow_forward
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