Concept explainers
Interpretation:
The reason behind the formation of a conjugate diene by dehydrohalogenation of 1,2-dibromocyclcohexane, when, generally, dehydrohalogenation of dihalides leads to
Concept introduction:
舧 Electrophiles are electron-deficient species, which has positive or partially positive charge. Lewis acids are electrophiles, which accept electron pair.
舧 Nucleophiles are electron-rich species, which has negative or partially negative charge. Lewis bases are nucleophiles, which donate electron pair.
舧 Free radical is an atom, molecule, or ion that has an unpaired electron, which makes it highly chemically reactive.
舧 Substitution reaction: A reaction in which one of the hydrogen atoms of a hydrocarbon or a
舧 Elimination reaction: A reaction in which two substituent groups are detached and a double bond is formed is called elimination reaction.
舧 Addition reaction: It is the reaction in which unsaturated bonds are converted to saturated molecules by the addition of molecules.
舧 The reaction in which the halide group and hydrogen group are removed to form
舧 The reaction in which hydrogen is added to the compound in the presence of catalyst is known as hydrogenation.
舧 The number of moles of hydrogen absorbed will be equal to the number of double bonds.
舧 Alkynes are synthesized by dehydrohalogenation of dihalides using a strong base and a strong nucleophile via E2 elimination reaction.
舧 The linear nature of the
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Organic Chemistry
- Account for the fact that addition of HCl to 1-bromopropene gives exclusively 1-bromo-1-chloropropane. CH₂CH=CHBr + HCl CH₂CH₂CHBrCl 1-Bromo-1-chloropropane 1-Bromopropene Account for the fact that treating propenoic acid (acrylic acid) with HCl gives only 3-chloropropanoic acid. CH₂=CHCOH + HCl Propenoic acid (Acrylic acid) Br L OH CICH₂CH₂COH 3-Chloropropanoic acid (b) Draw a structural formula for the alkene with the molecular formula C-H₁0 that reacts with Br, and water to give each product. 10 OH Br (c) HO | || CH₂CHCOH Br 2-Chloropropanoic acid L(this product is not formed)_arrow_forwardFree-radical chlorination of hexane gives very poor yields of 1-chlorohexane, while cyclohexane can be converted to chlorocyclohexane in good yield. How do you account for this difference?arrow_forwardcis-1-Bromo-4-tert-butylcyclohexane and trans-1-bromo-4-tert-butylcyclohexane both react with sodium ethoxide in ethanol to form 4-tert-butylcyclohexene. Explain why the cis isomer reacts much more rapidly than the trans isomer.arrow_forward
- Classify the following dienes and polyenes as isolated, conjugated, cumulated, or some combination of these classifications.arrow_forwardAccount for the fact that the bicyclic ether (3) is formed from the trans isomer but not from the cis isomer.arrow_forwardAccount for the fact that addition of HCl to 1-bromopropene gives exclusively 1-bromo-1-chloropropane.arrow_forward
- Bicyclo-2,5-heptadiene can be prepared in two steps from cyclopentadiene and vinyl chloride. Provide a mechanism for each step.arrow_forwardElimination 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.arrow_forwardFree-radical chlorination of hexane gives very poor yields of 1-chlorohexane, while cyclohexane can be converted to chlorocyclohexane in good yield. What ratio of reactants (cyclohexane and chlorine) would you use for the synthesis of chlorocyclohexane?arrow_forward
- The Diels–Alder reaction between butadiene and dimethyl maleate yields a ring structure, as shown in the product. Complete the structure by drawing any missing bonds and indicating the stereochemistry of the new stereocenters.arrow_forwardDraw an approximate reaction-energy diagram showing the curves for the two possible pathways for ionic addition of HBr to 1-methylcyclohexene. (a) Formation of the major product, 1-bromo-1-methylcyclohexane, and (b) formation of the minor product, 1-bromo-2-methylcyclohexane. Point out how these curves show that 1-bromo-1-methylcyclohexane should be formed fasterarrow_forwardLike alkenes, conjugated dienes can be prepared by elimination reactions. Draw a stepwise mechanism for the acid-catalyzed dehydration of 3-methylbut-2-en-1-ol [(CH3)2C=CHCH2OH] to isoprene [CH2=C(CH3)CH=CH2].arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning