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- cis-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.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.Which isomer of 1-bromo-3-isopropylcyclohexane reacts faster when refluxed with potassium tert-butoxide, the cis isomer or the trans isomer? Draw the structure of the expected product from the faster-reacting compound.
- Chlordane, 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?A student obtained two products from the reaction of 1,3-cyclohexadiene with Br2 (disregarding stereoisomers). His lab partner was surprised when he obtained only one product from the reaction of 1,3-cyclohexadiene with HBr (disregarding stereoisomers). Account for these results.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.
- 1,3-Cyclohexadiene and 1,4-cyclohexadiene can be distinguished by reaction with ozone and then treatment with zinc. Draw the structures of the products produced by ozonolysis of the two compounds.Bicyclo-2,5-heptadiene can be prepared in two steps from cyclopentadiene and vinyl chloride. Provide a mechanism for each step.Write the monobromination products of 1,4-dimethylcyclohexane and calculate the percentages of each product. Which is the major product?
- It is known that a 1,4 - cyclohexadiene compound undergoes an isomerization process to become 1,3 - cyclohexadiene in the presence of an acid. There are 2 possible mechanisms for the isomerization reaction, namely: If 3,3,6,6 - tetradeuterio - 1,4 - cyclohexadiene is reacted with an acid so that it undergoes an isomerization reaction to become 1,2,5,5 - tetradeuterio - 1,3 - cyclohexadiene. Which is the preferred mechanism path? Explain why! (Note: the C - H bond is weaker than the C - D bond)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)_What are the starting reactants for the following reaction? 4 X = cyclohexa-1,3-diene; Y = ethyl acrylate X = cyclopenta-1,3-diene; Y = acrylaldehyde X = cyclohexa-1,3-ene; Y = ethyl acrylate X = hexa-1,3-diene; Y = ethyl propiolate CO₂C₂H5