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- two positions of anthracene sometimes react more like polyenes thanlike aromatic compounds.(a) Draw a Kekulé structure that shows how the reactive positions of anthracene are the ends ofa diene, appropriate for a Diels–Alder reaction.(b) The Diels–Alder reaction of anthracene with maleic anhydride is a common organic labexperiment. Predict the product of this Diels–Alder reaction.A solution of 5-methylcyclopenta-1,3-diene rearranges at roomtemperature to a mixture containing 1-methyl-, 2-methyl-, and 5-methylcyclopenta-1,3-diene. (a) Show how both isomeric products areformed from the starting material by a sigmatropic rearrangementinvolving a C–H bond. (b) Explain why 2-methylcyclopenta-1,3-diene isnot formed directly from 5-methylcyclopenta-1,3-diene by a [1,3]rearrangement.The Grignard reagent is reacted with oxethane (four-ring cyclic ether) to giveprimary alcohol, but the reaction is slower than the reaction between ethyleneoxides. Write down the reasons for the reaction and explain the reasons why there was a differencethe reactivity between oxethane and ethylene oxide?
- provide the vond line structure of the organic product obtained following the reactions and for each step of the given reaction scheme.The treatment of isoprene [CH2=C(CH3)CH=CH2] with one equivalent ofmCPBA forms A as the major product. A gives a molecular ion at 84 in itsmass spectrum, and peaks at 2850–3150 cm−1 in its IR spectrum. The 1HNMR spectrum of A is given below. What is the structure of A?(a) For the reaction of 1-methoxy-4-methylbenzene with CH3C(O)CI in the presence of AICI3, describe the bonding and electron distribution in 1-methoxy- 4-methylbenzene, formation and structure of the electrophile in the reaction, and the most stable intermediate responsible for the end product. i H3C1 CI, AICI 3 Me- -OMe 1-methoxy-4-methylbenzene (b) Use phenol as the substrate, propose a synthetic scheme to produce 2-allyl-4-bromophenol (Mechanism not required). Br OH OH phenol 2-allyl-4-bromophenol (c) Propose a synthesis of Compound A starting from benzaldehyde and other necessary reagents of your choice (Mechanism not required). OH CHO CI. Compound A benzaldehyde (d) For the given 13C NMR chemical shifts of the carbonyl carbons in the order of ketones > aldehydes > carboxylic acids, provide an explanation. O CH3 H3C. 13C NMR Chemical Shifts: H₂C1 H₂C H > OH 200 ppm 181 ppm 209 ppm
- Hydrocarbon 10 and ester 12 react upon heating to give a cycloaddition product D. (i) Suggest a structure for product D and provide a curved arrow mechanism that accounts for its formation. (ii) Draw the molecular orbitals corresponding to the HOMO of 10 and the LUMO of 12 and show that these are of suitable symmetry for a concerted cycloaddition to take place. (iii) Use frontier molecular orbital theory to account for the observation that the formation of D is faster in the presence of AlCl3. please answer all thank youV) Outline a synthesis of the following compound from benzene and other appropriate organic or inorganic reagents. ? CH3 ? CO2H Excess ?3. (a) The 3C-NMR spectrum of one of the three xylenes (dimethyl benzenes) show resonance at 8 = 10 1, 126-2, 130-0 and 138-8 ppm (proton deccupled). ident:fv the structure of the xylene and ass:gn %3D the &-values.
- One step in the synthesis of dodecahedrane involves reaction of the tetraene C with dimethylacetylene dicarboxylate (D) to afford two compounds having molecular formula C16H16O4. This reaction has been called a domino Diels–Alder reaction. Identify the two products formed.(a) Draw a Kekulé structure that shows how the reactive positions of anthracene are the ends of a diene, appropriate for a Diels–Alder reaction.(b) The Diels–Alder reaction of anthracene with maleic anhydride is a common organic lab experiment. Predict the product of this Diels–Alder reaction.divls depends oin the moisture content of the reaction mixture. Propose a detailed mechanism for ench of the following steps to account for the observed The outeome of oxidation of alkenes with 1odine and silver acetate to afford stereochemistry of the product HO () 2, 2 RCO2Ag (i1) NaOH (aq) HO HO () 2, RCO2Ag, H20 (11) NaOH (aq) HO