Interpretation:
Given that cis- and trans-isomers of 2-butene give different cyclopropane products in the Simmons-Smith reaction. The structures of both the products are to be given and the difference is to be explained.
Concept introduction:
The reaction given is an example of Simmons-Smith reaction. When CH2I2 is treated with Zn/Cu couple, iodomethylzinc iodide, ICH2ZnI, is formed. This ICH2ZnI transfers a CH2 group to the double bond in
To give:
The structures of the products produced when cis- and trans-isomers of 2-butene react in Simmons-Smith reaction and to explain the difference.
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Chapter 8 Solutions
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- 4-methyl-3-hexanol was prepared by reacting an alkene with either hydroboration-oxidation or oxymercuration-reduction. Draw the structure of the alkene that was used to prepare the alcohol in highest yield. • You do not have to consider stereochemistry. • Indicate the method of preparation by drawing either BH3 (for . If there is more than one alkene that can be used for a given method, draw all of them. If either hydroboration-oxidation or oxymercuration-reduction can be used, just give the structures for one method. Separate structures with + signs from the drop-down menu. ● 981 -- 26224 ? ChemDoodle Y hydroboration-oxidation), or Hg (for oxymercuration-reduction), in a separate sketcher. Sn [1arrow_forwardWrite the monobromination products of 1,4-dimethylcyclohexane and calculate the percentages of each product. Which is the major product?arrow_forwardWrite a conformational structure for 1,2,3-trimethylcyclohexane in which all the methyl groups are axial and then show its more stable conformation.arrow_forward
- The major product formed when methylenecyclohexane is treated with NBS in dichloromethane is 1-(bromomethyl)cyclohexene. Account for the formation of this product.arrow_forwardConsider the following proposed structures for benzene, each of which is consistent with the molecular formula C6H6. (iv) CH3CCCCCH3 (v) CH2=CHCCH=CH2 When benzene reacts with chlorine to give C6H5Cl, only one isomer of that compound forms. Which of the five proposed structures for benzene are consistent with this observation? When C6H5Cl reacts further with chlorine to give C6H4Cl2, exactly three isomers of the latter compound form. Which of the five proposed structures for benzene are consistent with this observation?arrow_forward2-chloropropane is a major product of the reaction of chlorine with propane under ultraviolet light. Write the mechanism for this reaction including the initiation step and the two propagation steps.arrow_forward
- Explain the hybridisation of electron orbitals in a carbon atom (sp, sp2 and sp3), giving a detailed explanation, supported by suitable examples, of how sigma (s) and pi (p) bonds are formed. 2 Explain why alkenes are much more reactive than alkanes towards chlorine (C12) or bromine (Br2) in the dark at room temperature, and why alkanes do not react with HCI (g) or HBr (g) whereas alkenes do. please provide a diagram as wellarrow_forwardWhen cyclopropane is treated with HI, 1-iodopropane is formed. A similar type of reaction does not occur with cyclopentane or cyclohexane. Suggest an explanation for cyclopropane’s reactivity.arrow_forwardsketch the various conformational isomers of 1,3-dimethylcyclohexane. Indicate the position (axial/equatorial) of each of the methyl groups in each structure.arrow_forward
- 21.) Calculate the enthalpy of hydrogenation of benzene to cyclohexane from the following reactions A,H (kJ/mol) C6H6 (1) + 15/2 02 (g) → 6 CO2 (g) + 3 H20 (1) C6H12 (1) + 9 02 (g) → 6 CO2 (g) + 6 H20 (1) H2 (g) + ½ 02 (g) → H2O (1) -3268 -3920 -285.83 a.) -205 kJ/mol b.) -1507 kJ/mol c.) -938 kJ/mol d.) -366 kJ/molarrow_forwardPhotochemical chlorination of 2,2,4-trimethylpentane gives four isomeric monochlorides. (a) Write structural formulas for these four isomers. (b) The two primary chlorides make up 65% of the monochloride fraction. Assuming that all the primary hydrogens in 2,2,4-trimethylpentane are equally reactive, estimate the percentage of each of the two primary chlorides in the product mixture.arrow_forward(B) a What alkane should be used to synthesize the 1- bromo -1- ethyl cyclohexane? Write a chemical reaction and explain b. Write a chemical reaction and name the product formed when 3- pentanol undergoes dehydration c. Comment on kinetic stability or thermodynamic stability of an organic compoundarrow_forward
- Principles of Modern ChemistryChemistryISBN:9781305079113Author:David W. Oxtoby, H. Pat Gillis, Laurie J. ButlerPublisher:Cengage LearningOrganic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
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