Chlorination of 1,3,5‑trimethylcyclohexane via radical halogenation leads to the formation of several monohalogenated products. Identify the products, then estimate the relative percentages of each product. Step 1: A monochlorination reaction will substitute a proton for a chlorine. Start by identifying all the unique positions that can be halogenated. Ignore stereochemistry

Chlorination of 1,3,5‑trimethylcyclohexane via radical halogenation leads to the formation of several monohalogenated products. Identify the products, then estimate the relative percentages of each product. Step 1: A monochlorination reaction will substitute a proton for a chlorine. Start by identifying all the unique positions that can be halogenated. Ignore stereochemistry

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter10: Organohalides

Section10.SE: Something Extra

Problem 24AP: Draw and name all of the monochlorination products that you might obtain from the radical...

See similar textbooks

Similar questions

Free radical halogenation is used to replace one or more hydrogens on an alkane with one or more halogens (either chlorine or bromine). It is a substitution reaction. A student performs a free radical bromination on 3-methyl-pentane (5.88 g) to create the desired product of 3-bromo-3-methyl-pentane. The product mix, which hopefully contains almost all 3-bromo-3-methyl-pentane, is cleaned up by passing it through a gas chromoatograph, which separates out the 3-bromo-3-methyl-pentane from any undesired products made during the reaction (undesired products are created frequently in free radical halogenation). The initial product mix weighed 9.45 g; the purified 3-bromo-3-methyl-pentane weighed 7.21 g. What is the student's percent recovery?
When free radical halogenation is performed with one of the compounds below, only a single product with the formula C5H11Cl is isolated. Which compound fits this description? Select one: a. 2,2-dimethylpropane b. cyclopentane c. pentane d. 2-methylbutane
Identify two alkenes that react with HBr to form 1-bromo-1-methylcyclohexane without undergoing a carbocation rearrangement.
For each alkane, which mono brominated derivatives could you form in good yield by free-radical bromination?(a) cyclopentane (b) methylcyclopentane(c) 2-methylpentane (d) 2,2,3,3-tetramethylbutane
Reaction of 2-methyl-2-butene (above) with HBr might, in principle, lead to a mixture of two alkyl bromide addition products. Draw these two alkyl bromides.
Draw and name all of the monochlorination products that you might obtain from the radical chlorination of the compounds below. Which of the products are chiral? Are any of the products optically active? (a) 2-methylbutane (b) methylcyclopropane (c) 2,2-dimethylpentane
Following is a balanced equation for bromination of toluene. (a) Using the values for bond dissociation enthalpies given in Appendix 3, calculate H0 for this reaction. (b) Propose a pair of chain propagation steps and show that they add up to the observed reaction. (c) Calculate H0 for each chain propagation step. (d) Which propagation step is rate-determining?
Alcohols are important for organic synthesis, especially in situations involving alkenes. The alcohol might be the desired product, or the OH group might be transformed into another functional group via halogenation, oxidation, or perhaps conversion to a sulfonic ester derivative. Formation of an alcohol from an alkene is particularly powerful because conditions can be chosen to produce either the Markovnikov or non-Markovnikov product from an unsymmetrical alkene. Using your reaction roadmap as a guide, show how to convert 4-methyl-1-pentene into 5-methylhexanenitrile. You must use 4-methyl-1-pentene and sodium cyanide as the source of all carbon atoms in the target molecule. Show all reagents needed and all molecules synthesized along the way.
Alkenes can be hydrated to form alcohols by (1) hydroboration followed by oxidation with alkaline hydrogen peroxide and (2) acid-catalyzed hydration. Compare the product formed from each alkene by sequence (1) with those formed from (2). Q.)Cyclopentene
1. Predict the elimination products of the following reactions. When two alkenes are possible, predict which one will be the major product. Explain your answers, showing the degree of substitution of each double bond in the products. 2. Which of these reactions are likely to produce both elimination and substitution products? (a) 2-bromopentane +NaOCH3 (b) 3-bromo-3-methylpentane +NaOMe(Me= methyl, CH3) (c) 2-bromo-3-ethylpentane +NaOH (d) cis-1-bromo-2-methylcyclohexane +NaOEt (Et= ethyl, CH2CH3)
Consider the compound 3(S),5,5-trimethyl cyclohexane. Upon reduction with H2 on a 1% Pt/C catalyst, draw the equation for this reaction, find out the absolute configuration of the product and explain why the absolute configuration is completely inverted in this reaction
Alkenes can be hydrated to form alcohols by (1) hydroboration followed by oxidation with alkaline hydrogen peroxide and (2) acid-catalyzed hydration. Compare the product formed from each alkene by sequence (1) with those formed from (2). Q.)1-Methylcyclohexene