What product(s) would you expect from reaction of (S)-3-chloro-3- methylheptane with acetic acid? Show the stereochemistry of both reactant and product.
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- Draw the structure of (2Z, 6E)-3-ethyl-7-methyldeca-2, 6-dien-1-ol, the sex pheromone of the codling moth, a common agricultural pest that destroys apple crops. By spraying an apple orchard with this pheromone, the mating of male and female moths is disrupted, and moth populations can be controlled.Propose 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)One 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'?
- A certain compound of molecular formula C19H38 was isolated from fish oil and from plankton. On hydrogenation it gave 2,6,10,14-tetramethylpentadecane. Ozonolysis gave (CH3)2C O and a 16-carbon aldehyde. What is the structure of the natural product? What is the structure of the aldehyde?The bicyclic alkene P can be prepared by thermal electrocyclic ring closure from cyclodecadiene Q or by photochemical electrocyclic ring closure from cyclodecadiene R. Draw the structures of Q and R, and indicate the stereochemistry of the process by which each reaction occurs.The reaction of (2S)-2-chloro-3-methylpentane with sodium iodide yields two products: (2R)-2-iodo-3-methylpentane and racemic 3-iodo-2-methylpentane. Account for the formation of each of these two products. For each product, you should show how it is formed and what that tells you about the mechanism of that specific reaction.
- (a) Draw the products (including stereoisomers) formed when 2methylhex-2-ene is treated with HBr in the presence of peroxides. (b) Draw the products (including stereoisomers) formed when (S)-2,4dimethylhex-2-ene is treated with HBr and peroxides under similar conditions.H3C N- H₂NNH₂ H⭑ CH3 H3C IN CH3 Hydrazine reacts with 2,4-pentanedione to yield 3,5-dimethylpyrazole. Including protonations and deprotonations, the reaction takes 12 steps. Write out the mechanism on a sheet of paper and then draw the structure of the product of step 6. • You do not have to consider stereochemistry. •You do not have to explicitly draw H atoms. • Do not include lone pairs in your answer. They will not be considered in the grading. • In an elimination step, include the structure of the leaving group, but draw it in its own sketcher. Separate structures with + signs from the drop-down menu. ? Sn th Previous NextDraw a structural formula for the major organic product of the following reaction: CH3 CH3 ● CH3 CH3 AAVIL + Br₂ Show product stereochemistry IF the reactant alkene has both carbons of the double bond within a ring. • Do not show stereochemistry in other cases. ● If enantiomers are formed, just draw one. CH₂Cl₂ Sn [F ? ChemDoodleⓇ
- Using cis- and trans-hex-3-ene, demonstrate that the addition of HCl is not a stereospecic reaction. Draw the structure of the stereoisomers formed from each alkene.The optically active (2R)-2-phenyl-2-butanol reacts in hydrochloric acid to form haloalkanes and alkenes. The substitution reaction is reported to occur with 100% racemization. Give the structures of the enantiomers that form during the substitution and indicate how much of each is formed. Propose a mechanism for the substitution reaction to yield the R product. What reagents would you use to achieve 100% retention of configuration. Two geometric isomers are obtained during the elimination reaction. Explain mechanistically which alkene will be the main product.The two stereoisomers of cinnamic acid (C6H5CH=CHCO2H) each give a different product on reaction with 1,3-butadiene. Write an equation for each reaction.