Interpretation:
The reaction when hydrogen chloride reacts with 2-methyl-1,3-butadiene to form 1-chloro-3-methyl-2-butene as a major product via 1,4-addition mechanism and no product formed by 1,2-additon, is to be explained.
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 functional group is substituted by any other functional group is called substitution reaction.
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 there is addition of hydrogen molecule is called hydrogenation reaction.
舧
舧 Hydrogenation with platinum as a catalyst is used to convert unsaturated carbohydrates to saturated hydrocarbons
舧 Oxidation of
舧 Ozonolysis helps convert the carbon–carbon double bonds to carbon–oxygen double bond (carbonyl compounds).
舧 Dimethyl sulfide is used as a reducing agent that decomposes the intermediate formed into the carbonyl group.
舧 NBS (nitro-bromo succinimide) is a special reagent used for bromination of allylic carbocations.
舧 Bromine replaces the hydrogen attached to the carbon adjacent to the carbon bearing double bond.
舧 This method of using NBS can produce allylic bromides without bromine reacting with the double bond.
舧 Dehydration of a primary alcohol in the presence of a mineral acid like concentrated sulfuric acid results in the formation of alkene via E2 elimination.
舧 The stability of carbocation:
舧 The 1,2 – addition to a diene is the addition of an electrophile to the carbon designated as 1 and a nucleophile to the carbon designated as 2. The positions of carbons as 1 and 2 are not according to the IUPAC numbering of the molecule, but as a conjugated diene molecule. 1,4-addition results in addition of hydrogen to thee carbon designated as 1 and a halogen to the carbon designated as 4.
舧 The mechanism of 1,2 addition and 1,4-addition of hydro halogenation is given below:
Want to see the full answer?
Check out a sample textbook solutionChapter 13 Solutions
Organic Chemistry, 12e Study Guide/Student Solutions Manual
- Acid-catalyzed dehydration of 3,3-dimethyl-2-butanol gives three alkenes: 2,3-dimethyl-2-butene, 3,3-dimethyl- 1-butene, and 2,3-dimethyl-1-butene. Draw the structure of the carbocation intermediate leading to the formation of 2,3-dimethyl-2-butene. • You do not have to consider stereochemistry. • You do not have to explicitly draw H atoms. • If more than one structure fits the description, draw them all. • Separate structures with + signs from the drop-down menu. / H₂C CH₂ CH3 CH3 ChemDoodleⓇ On []arrow_forwardChlordane, 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_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_forward
- Below are the structures for trans-1-chloro-2-t-butylcyclohexane and cis-1- chloro-2-t-butylcyclohexane. Both molecules can react with a base to form an alkene. cis-1-chloro-2-t-butylcyclohexane reacts 10x faster than trans-1-chloro2-t-butylcyclohexane. Use chair conformations to explain why the cis isomer is more reactive.arrow_forwardAddition of HCl to 3-methyl-1-pentene gives two products. One of these is 2-chloro-3-methylpentane. What is the other product?arrow_forwardWhen 2-bromo-2-methylbutane is treated with a base, a mixture of 2-methyl-2-butene and 2-methyl-1- butene is produced. When potassium hydroxide is the base, 2-methyl-1-butene accounts for 45% of the product mixture. However, when potassium tert-butoxide is the base, 2-methyl-1-butene accounts for 70% of the product mixture. What percent of 2-methyl-1-butene would be in the mixture if potassium propoxide were the base? base Br A. Less than 45% B. C. 45% Between 45% and 70% D. More than 70%arrow_forward
- Reaction of HBr with 3-methylcyclohexene yields a mixture of four products: cis-and trans-1-bromo-3-methylcyclohexane and cis-and trans-1-bromo-2-methylcyclohexane. The analogous reaction of HBr with 3-bromocyclohexene yields trans-1, 2-dibromocyclohexane as the soleproduct. Draw structures of the possible intermediates, and then explain why only a single product is formed in this reaction.arrow_forwardNAME and DRAW the STRUCTURE of ALL the alkenes which could undergo catalytic hydrogenation at 900°C to form methylcyclopentane. Circle the alkene with the HIGHEST stability and X the alkene with the HIGHEST heat of hydrogenation. Give reasons for your choice.arrow_forwardPropose a synthesis for the systemic agricultural fungicide tridemorph from dodecanoic acid (lauric acid), propene, and a one-carbon building block. How many stereoisomers are possible for tridemorph? CH3 →CH3(CH2)10COOH + CH3CH=CH, H3C (CH2) 12CH3 Tridemorph Dodecanoic acid Propene (Lauric acid)arrow_forward
- A chemist allows some pure (2S,3R)-3-bromo-2,3-diphenylpentane to react with a solution of sodium ethoxide(NaOCH2 CH3) in ethanol. The products are two alkenes: A (cis-trans mixture) and B, a single pure isomer. Under the same conditions, the reaction of (2S,3S)-3-bromo-2,3-diphenylpentane gives two alkenes, A (cis-trans mixture) and C. Upon catalytic hydrogenation, all three of these alkenes (A, B, and C) give 2,3-diphenylpentane. Determine the structures of A, B, and C; give equations for their formation; and explain the stereospecificity of these reactions.arrow_forwardPhineas and Ferbs, two brothers who enjoy vacations, doing fun things every summer. This summer the brothers and their friends carry out an organic synthesis with an unknown compound (L1) that contains 52% Carbon, 6% Hydrogen and 42% bromine, this compound (L1) is treated with magnesium in ether to obtain L2 , which reacts violently with D2O for 1-methyl cyclohexene with a deuterium atom in the methyl group (L3). The L2 reaction is treated with acetone followed by hydrolysis to give L4. Heating L4 with concentrated sulfuric acid gives L5, which decolors the bromine, obtaining L6. L5 undergoes hydrogenation with excess hydrogen and platinum as a catalyst giving rise to isobutyl cyclohexane. Determine the structures of compounds L1 through L6.arrow_forwardCyclobutane reacts with bromine to give bromocyclobutane, but bicyclobutane reacts with bromine to give 1,3-dibromocyclobutane. Account for the differences between the reactions of these two compounds. heat + Br2 -Br + HBr Cyclobutane Bromocyclobutane heat Br2 Br Br Bicyclobutane 1,3-Dibromocyclobutanearrow_forward
- ChemistryChemistryISBN:9781305957404Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCostePublisher:Cengage LearningChemistryChemistryISBN:9781259911156Author:Raymond Chang Dr., Jason Overby ProfessorPublisher:McGraw-Hill EducationPrinciples of Instrumental AnalysisChemistryISBN:9781305577213Author:Douglas A. Skoog, F. James Holler, Stanley R. CrouchPublisher:Cengage Learning
- Organic ChemistryChemistryISBN:9780078021558Author:Janice Gorzynski Smith Dr.Publisher:McGraw-Hill EducationChemistry: Principles and ReactionsChemistryISBN:9781305079373Author:William L. Masterton, Cecile N. HurleyPublisher:Cengage LearningElementary Principles of Chemical Processes, Bind...ChemistryISBN:9781118431221Author:Richard M. Felder, Ronald W. Rousseau, Lisa G. BullardPublisher:WILEY