Concept explainers
Interpretation:
The reagents required to convert 2,3-dimethyl-1,3-butadiene to the given products are to be provided.
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 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 Alkenes react with bromine and form alkyl dihalides. The product stereochemistry is dependent on the stereochemistry of the reactant alkene.
舧 The 1,2 – addition of hydrohalogenation (HX) to a diene is the addition of hydrogen to the carbon designated as 1 and halogen to the carbon designated as 2. But the positions of carbons as 1 and 2 are not according to the IUPAC numbering of the molecule but as a conjugated diene. The mechanism is similar with 1,4-addition.
舧 The mechanism of 1,2 addition and 1,4-addition of hydrohalogenation is given below:
Want to see the full answer?
Check out a sample textbook solutionChapter 13 Solutions
Organic Chemistry
- Write the structure of the major organic product formed in the reaction of each of the following with hydrogen bromide in the absence of peroxides and in their presence. (a) 1-Pentene (b) 2-Methyl-2-butene (c) 1-Methylcyclohexenearrow_forwardDraw a structural formula for the alcohol formed by treating each alkene with borane in tetrahydrofuran (THF) followed by hydrogen peroxide in aqueous sodium hydroxide, and specify stereochemistry where appropriate. (a) (d) (b) (e) (c)arrow_forward(a) Cyclohexa-1,3-diene can be converted into a tetrasubstituted haloalkane when reacted with bromine in ether. Write a balanced chemical equation for the reaction that occurs and state the expected observation. (b) Compound A and B are alkenes with the same molecular formula C5H10. Compound A is a branched-chain alkene while compound B is a straight-chain alkene. The reaction between compound A with hydrogen bromide produces major product C which is optically active. (i) Draw TWO (2) possible structures for compound B. (ii) Outline the mechanism for the reaction between compound A with hydrogen bromide to form major product C. (iii) Name the product formed when compound A undergoes bromination reaction.arrow_forward
- Give the structure, exclusive of stereochemistry, of the principal organic product formed on reaction of 2,3-dimethyl-1,3-butadiene with each of the following:(a) 2 mol H2, platinum catalyst(b) 1 mol HCl (product of 1,2-addition)(c) 1 mol HCl (product of 1,4-addition)(d) 1 mol Br2 (product of 1,2-addition)(e) 1 mol Br2 (product of 1,4-addition)(f) 2 mol Br2arrow_forwardWrite structural formulas for the products that form when 1-butene reacts with each of the following reagents: (a) HI (b) H2, Pt (c) Dilute H2SO4, warm (d) Cold concentrated H2SO4 (e) Cold concentrated H2SO4, then H2O and heat (f) HBr (g) Br2 in CCl4 (h) Br2 in H2O (i) HCl (j) O3, then Me2S (k) OsO4, then NaHSO3/H2O (l) KMnO4, OH-, heat, then H3O+ (m) Hg(OAc)2 in THF and H2O, then NaBH4, OH- (n) BH3:THF, then H2O2, OH-arrow_forwardDevelop syntheses for the following compounds. As starting materials, you may use cyclopentanol, alcohols containing no more than four carbon atoms, and any common reagents and solvents. (a) trans-cyclopentane-1,2-diol (b) 1-chloro-1-ethylcyclopentanearrow_forward
- Starting from bromoethane, the formation of which of the following compound requires more than one step of reaction? 2 (a) Methoxyethane (b) Ethanol (c) Ethanoic acid (d) Ethenearrow_forwardCompound 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, CH2Cl2. (i) Draw and name the structure of compound D. (ii) Draw two (2) constitutional isomers of compound D.arrow_forwardCompund ( A) C6H12 is treated with chlorine in the presence of carbon tetrachloride to given (B)C6H12Cl2.Compund (B) is treated with alcoholic KoH,followed by NaNH2 ,resulting in this formation of (C).compound (C) is treated with hydrogen in the presence of nickel catalysts to give 2methylpentane. Compound (C) does not react with sodamide or ammonical solution of silver nitrate .Ozonolysis of (A) give two aldehyde, (D) and (E) .Compound (E) is identified as acetaldehyde .From this information,describe the structural formula (A) ,(B) ,(C) And (C).write equation for all reactionarrow_forward
- (a) (b) (c) Suggest a synthesis of the following alkene (A) using a Wittig reaction strategy. Draw the starting material(s), key reagent and a full reaction mechanism including an explanation of the observed geometry. Which of the following (B) and (C) will favour the enol form? Briefly explain your reasoning. Predict the product(s) and provide a mechanism for each of the following transformations: (i) (ii) OMe OMe Base OEt NaOEtarrow_forward1. (a) Describe aromaticity, Kekule structure and resonance structure for benzene. (b) Why is benzene more stable than aliphatic alkenes?arrow_forwardExplain why :(a) The dipole moment of chlorobenzene is lower than that of cyclohexyl chloride.(b) Alkyl halides, though polar, are immiscible with water.arrow_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