Organic Chemistry. Carey/Giuliano 10th edition. Chapter 10

Transcription

1 Organic Chemistry Carey/Giuliano 10th edition Chapter 10 Copyright 2017 McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education.

2 Question 1 Which radical structure is more stable? A) I B) II C) III D) IV I III II IV

3 Question 2 What is the correct order of steps involved in a freeradical chain reaction? A) propagation, initiation, chain-termination B) chain-termination, initiation, propagation C) initiation, chain-termination, propagation D) initiation, propagation, chain-termination

4 Question 3 How many constitutionally isomeric monochlorinated products are possible in the following reaction? A) 3 B) 5 C) 6 D) 7 Cl 2, heat

5 Question 4 Choose the major product for the reaction: CH 3 Br 2, light Br CH 2 A) B) CH 3 Br CH 3 C) D) Br CH 3 Br

6 Question 5 Which of the following halide radicals is more sensitive to the stability of the radical intermediate in halogenation of an alkane, and is thus more selective? A) F B) Cl C) Br D) I

7 Question 6 Free-radical addition of HBr/peroxides to an alkene goes through A) a carbocation intermediate that is formed on the more substituted carbon. B) a carbocation intermediate that is formed on the least substituted carbon. C) a radical intermediate that is formed on the least substituted carbon. D) a radical intermediate that is formed on the most substituted carbon.

8 Question 7 What is the major product for the following reaction? HBr peroxides A) B) Br Br Br C) D)

9 Question 8 What is the starting material that forms the product shown with the conditions shown?? Na NH 3 A) B) C) D)

10 Question 9 What is the relationship between the two chair conformations below? A) conformational isomers B) constitutional isomers C) different compounds D) stereoisomers

11 Question 10 What is the relationship between the two cyclohexane chairs below? A) conformational isomers B) constitutional isomers C) stereoisomers D) different compounds

12 Question 11 Which of the following statements is not true concerning the chair-chair interconversion of trans-1,2-diethylcyclohexane? A) An axial group will be changed into the equatorial position. B) The energy of repulsions present in the molecule will be changed. C) Formation of the cis substance will result. D) One chair conformation is more stable than the other

13 Question 12 Which of the listed terms best describes the relationship between the methyl groups in the chair conformation of the substance shown? A) eclipsed B) trans C) anti D) gauche

14 Question 13 Which of the following has an equatorial methyl group in its most stable conformation? A) B) C) D)

15 Question 14 The structure shown is the carbon skeleton of adamantane, a hydrocarbon having a structure that is a section of the diamond lattice. Adamantane is: A) bicyclic B) tricyclic C) tetracyclic D) pentacyclic

16 Question 15 Which structure has the most strain? A) the eclipsed conformation of ethane B) the gauche conformation of butane C) the boat conformation of cyclohexane D) the skew boat conformation of cyclohexane

17 Question 16 What is the IUPAC name for the compound represented by the Newman projection? A) 1-tert-Butyl-1-isopropylethane B) 1-tert-Butyl-3-methylbutane C) 2-isopropyl-3,3-dimethylbutane D) 2,2,3,4-tetramethylpentane

18 Question 17 Which one of the following statements is true? A) Van der Waals strain in cis-1,2- dimethylcyclopropane is the principal reason for its decreased stability relative to the trans isomer. B) Cycloalkanes larger than cyclodecane rarely occur naturally because they are too strained. C) One mole of cyclohexane gives off less heat on being burned in air than one mole of any other cycloalkane. D) The principal source of strain in the gauche conformation of butane is torsional strain.

19 Question 18 Which of the following statements best describes the most stable conformation of trans-1,3-dimethylcyclohexane? A) Both methyl groups are axial. B) Both methyl groups are equatorial. C) One methyl groups is axial, the other equatorial. D) The molecule is severely strained and cannot exist.

20 Question 19 What is the relationship between the two structures shown? A) Constitutional isomers B) Stereoisomers C) Different drawings of the same conformation of the same compound. D) Different conformations of the same compound.

21 Question 20 The most stable conformation of the compound to the right has A) an axial methyl group and an axial ethyl group. B) an axial methyl group and an equatorial ethyl group. C) an equatorial methyl group and an equatorial ethyl group. D) an equatorial methyl group and an axial ethyl group.

22 Answer Key Chapter C 2. B 3. C 4. B 5. D 6. B 7. D 8. B 9. A 10. C 11. C 12. D 13. D 14. B 15. C 16. D 17. A 18. C 19. A 20. D