Organic Chemistry 6th Edition solutions

Organic Chemistry 6
Write a pair of chain propagation steps for the radical bromination of propane to give 1- bromopropane, and calculate DH for each propagation step and for the overall reaction.

Organic Chemistry 6
Given the solution to Example 8.5, predict the structure of the product(s) formed when 3-hexene is treated with NBS.

Organic Chemistry 6
Show the products of the following reaction and indicate the major one. O2, initiator CH3(CH2)4CH2CH CH2

Organic Chemistry 6
Predict the major product of the following reaction: Peroxides + HBr

Organic Chemistry 6
Give IUPAC names for the following compounds. Where stereochemistry is shown, include a designation of confi guration in your answer. (a) Br (b) H Br 3C (c) Br Br (d) Cl Cl (e) CH3 CH2(CH2)4CH3 H I Fischer projection (f) Br H F (g) (h) Br (i) Cl

Organic Chemistry 6
Draw structural formulas for the following compounds. (a) 3-Iodo-1-propene (b) (R)-2-Chlorobutane (c) meso-2,3-Dibromobutane (d) trans-1-Bromo-3-isopropylcyclohexane (e) 1-Iodo-2,2- dimethylpropane (f) Bromocyclobutane

Organic Chemistry 6
Water and dichloromethane are insoluble in each other. When each is added to a test tube, two layers form. Which layer is water and which is dichloromethane?

Organic Chemistry 6
The boiling point of methylcyclohexane (C7H14, MW 98.2) is 101C. The boiling point of perfluoromethylcyclohexane (C7F14, MW 350) is 76C. Account for the fact that although the molecular weight of perfluoromethylcyclohexane is over three times that of methylcyclohexane, its boiling point is lower than

Organic Chemistry 6
Account for the fact that, among the chlorinated derivatives of methane, chloromethane has the largest dipole moment and tetrachloromethane has the smallest dipole moment. Molecular Dipole Moment Name Formula (debyes, D) Chloromethane CH3Cl 1.87 Dichloromethane CH2Cl2 1.60 Trichloromethane CHCl3 1.01

Organic Chemistry 6
Name and draw structural formulas for all possible monohalogenation products that might be formed in the following reactions. light (a) 1 Cl2 (b) light 1 Cl2 (c) light 1 Br2

Organic Chemistry 6
Which compounds can be prepared in high yield by halogenation of an alkane? (a) 2-Chloropentane (b) Chlorocyclopentane (c) 2-Bromo-2-methylheptane (d) (R )-2-Bromo-3-methylbutane (e) 2-Bromo- 2,4,4-trimethylpentane (f ) Iodoethane

Organic Chemistry 6
There are three constitutional isomers with the molecular formula C5H12. When treated with chlorine at 300C, isomer A gives a mixture of four monochlorination products. Under the same conditions, isomer B gives a mixture of three monochlorination products, and isomer C gives only one monochlorination

Organic Chemistry 6
Following is a balanced equation for bromination of toluene. C6H5CH3 1 Br2 C6H5CH2Br 1 HBr Toluene Benzyl bromide (a) Using the values for bond dissociation enthalpies given in Appendix 3, calculate DH for this reaction. (b) Propose a pair of chain propagation steps, and show that they add up to the

Organic Chemistry 6
Write a balanced equation and calculate DH for reaction of CH4 and I2 to give CH3I and HI. Explain why this reaction cannot be used as a method of preparation of iodomethane.

Organic Chemistry 6
Following are balanced equations for fl uorination of propane to produce a mixture of 1-fl uoropropane and 2-fl uoropropane. F Propane CH3CH2CH3 1 F2 1-Fluoropropane CH3CH2CH2F HF 1 Propane CH3CH2CH3 1 F2 2-Fluoropropane CH3CHCH3 1 HF Assume that each product is formed by a radical chain mechanism. (

Organic Chemistry 6
As you demonstrated in Problem 8.18, fl uorination of alkanes is highly exothermic. As per Hammonds postulate, assume that the transition state for radical fl uorination is almost identical to the starting material. With this assumption, estimate the fraction of each monofl uoro product formed in the

Organic Chemistry 6
Cyclobutane reacts with bromine to give bromocyclobutane, but bicyclobutane reacts with bromine to give 1,3-dibromocyclobutane. Account for the differences between the reactions of these two compounds. Cyclobutane heat Bromocyclobutane 1 Br2 Br 1 HBr Bicyclobutane heat 1,3- Dibromocyclobutane 1 Br2 B

Organic Chemistry 6
The fi rst chain propagation step of all radical halogenation reactions we considered in Section 8.5B was abstraction of hydrogen by the halogen atom to give an alkyl radical and HX, as for example CH3CH3 1 ? Br CH3CH2 ? 1 HBr Suppose, instead, that radical halogenation occurs by an alternative pair

Organic Chemistry 6
Following is a balanced equation for the allylic bromination of propene. CH2"CHCH3 1 Br2h CH2"CHCH2Br 1 HBr (a) Calculate the heat of reaction, DH, for this conversion. (b) Propose a pair of chain propagation steps, and show that they add up to the observed stoichiometry. (c) Calculate the DH for eac

Organic Chemistry 6
Using the table of bond dissociation enthalpies (Appendix 3), estimate the BDE of each indicated bond in cyclohexene. (a) (b) (c) H H H

Organic Chemistry 6
Propose a series of chain initiation, propagation, and termination steps for this reaction, and estimate its heat of reaction. Br light 1 Br2 1 HBr (racemic)

Organic Chemistry 6
The major product formed when methylenecyclohexane is treated with NBS in dichloromethane is 1- (bromomethyl)-cyclohexene. Account for the formation of this product.

Organic Chemistry 6
Draw the structural formula of the products formed when each alkene is treated with one equivalent of NBS in CH2Cl2 in the presence of light. (a) CH3CH CHCH2CH3 CH2 (b) (c)

Organic Chemistry 6
Calculate the DH for the following reaction step. What can you say regarding the possibility of bromination at a vinylic hydrogen? CH2"CH2 1 Br h CH2"CH 1 HBr

Organic Chemistry 6
Use the roadmap you made for problems 6.54 and 7.29, and update it to contain the reactions in the Key Reactions section of this chapter. Because of its highly specifi c nature, do not use reaction 3 of this chapter on your roadmap.

Organic Chemistry 6
Write the products of the following sequences of reactions. Refer to your roadmap to see how the combined reactions allow you to navigate between the different functional groups. (a) 1. Excess H2 / Pd 2. Br2 and light An alkyne (b) 1. H2 / Lindlar's catalyst 2. NBS and light An alkyne (c) 1. H2 / Lin

Organic Chemistry 6
Using your roadmap as a guide, show reagents and conditions to bring about these conversions, which may require more than one step. (a) Br (c) CH3CH CHCH3 (b) CH3CH CHCH3 CH3CH CHCH2Br CH3CH CHCH3 Br Br (racemic) (d) Br (e) Br (f) CH4 (Review section 7.5.) (g) Br (racemic)

Organic Chemistry 6
Predict the products of the following reactions. Where isomeric products are formed, label the major product. O2, initiator (a) (b) O2, initiator

Organic Chemistry 6
Give the major product of the following reactions. HBr peroxides (a) (b) HBr peroxides

Organic Chemistry 6
A major use of the compound cumene is in the industrial preparation of phenol and acetone in the two-step synthesis, shown below. O2 Initiator H3O+ OOH Chapter 16 Cumene Cumene hydroperoxide Phenol Acetone OH + O Write a mechanism for the fi rst step. We will see in Problem 16.65 how to complete the

Organic Chemistry 6
An important use of radical-chain reactions is in the polymerization of ethylene and substituted ethylene monomers such as propene, vinyl chloride (the synthesis of which was discussed in Section 7.6 along with its use in the synthesis of poly(vinyl chloride), (PVC)), and styrene. The reaction for th