Smith Conjugation, Resonance, And Dienes Exam Prep Ch.14

Organic Chemistry, 6e (Smith)

Chapter 14 Conjugation, Resonance, and Dienes

1) Which of the following dienes contain conjugated double bonds?

A) Only I and II

B) Only II and III

C) Only I and III

D) Only II and IV

2) Which of the following dienes contain isolated double bonds?

A) Only I and II

B) Only II and III

C) Only I and III

D) Only II and IV

3) Which of the following statements about resonance structures is true?

A) The placement of atoms is different.

B) The placement of p bonds is different.

C) The placement of s bonds is different.

D) The placement of nonbonded electrons is the same.

4) What is the hybridization around the indicated carbon atom in the following anion?

A) sp3

B) sp2

C) sp

D) p

5) What is the hybridization around the indicated oxygen atom in the following anion?

A) sp3

B) sp2

C) sp

D) p

6) Which of the following is (are) conjugated dienes?

A) Only I

B) Only II

C) Only I and II

D) I, II, and III

7) Which of the following compounds is conjugated?

A) I

B) II

C) III

D) IV

8) Which of the following conjugated dienes represent two conformations?

A) Only I and II

B) Only I and III

C) Only II and III

D) None of the choices

9) Rank the following dienes in order of decreasing heat of hydrogenation, putting the diene with the highest heat of hydrogenation first.

A) I > II > III

B) III > II > I

C) II > I > III

D) III > I > II

10) Rank the following compounds in order of increasing stability, putting the least stable first.

A) I < II < III

B) III < II < I

C) II < I < III

D) III < I < II

11) What is the reactive intermediate in the reaction of 1,3-diene with HBr, resulting in 1,4-addition?

A) Allylic radical

B) Cyclic bromonium

C) Dienophile

D) Allylic carbocation

12) Which of the following is the appropriate term for the mechanism of the addition of HBr to 1,3-dienes?

A) Nucleophilic addition

B) Electrophilic addition

C) Free radical addition

D) Conjugate addition

13) What is (are) the major product(s) of the following reaction?

A) Only I

B) Only II and IV

C) Only I and III

D) Only I, II, and III

14) What is (are) the major product(s) of the following reaction?

A) Only I

B) Only I and III

C) Only II and IV

D) Only I, II, and III

15) What is (are) the major product(s) of the following reaction?

A) Only I

B) Only II

C) Only I and II

D) I, II, and III

16) Which of the following is not a product obtained from the addition of 1 equivalent of HBr to (E)-1,3-pentadiene?

A) (E)-4-Bromo-2-pentene

B) (E)-1-Bromo-2-pentene

C) 3-Bromo-1-pentene

D) (E)-3-Bromo-2-pentene

17) What is the thermodynamic product obtained from the addition of 1 equivalent of HBr to 1,3-butadiene?

A) 3-Bromo-1-butene

B) 1-Bromo-2-butene

C) 2-Bromo-2-butene

D) 2-Bromo-1-butene

18) What is the kinetic product obtained from the addition of 1 equivalent of HBr to 1,3-butadiene?

A) 3-Bromo-1-butene

B) 1-Bromo-2-butene

C) 2-Bromo-2-butene

D) 2-Bromo-1-butene

19) Which of the following statements about kinetic vs. thermodynamic products is true?

A) The product that is formed faster is the thermodynamic product.

B) The kinetic product predominates at low temperature.

C) The product that predominates at equilibrium is the kinetic product.

D) The thermodynamic product is less stable.

20) Which of the following statements about the mechanism of the Diels-Alder reaction is true?

A) Three π bonds break; two σ bonds and one π bond form.

B) Three π bonds break; one σ bond and two π bonds form.

C) Two π bonds break; one σ bond and one π bond form.

D) Two π bonds break; two σ bonds and one π bond form.

21) Which of the following is not a feature of the Diels-Alder reaction?

A) They are initiated by peroxides.

B) They form new six-membered rings.

C) Three π bonds break.

D) They are concerted.

22) Rank the following dienes in order of increasing reactivity in a Diels-Alder reaction, listing the least reactive first.

A) I< II < III

B) III < I < II

C) II < I < III

D) I < III < II

23) Which of the following is the least reactive diene in a Diels-Alder reaction?

A) I

B) II

C) III

D) IV

24) Which of the following statements about the Diels-Alder reaction is true?

A) The diene can react only when it adopts the s-trans conformation.

B) Electron-withdrawing substituents in the diene increase reaction rate.

C) Electron-donating substituents in the dienophile increase the reaction rate.

D) The stereochemistry of the dienophile is retained in the product.

25) Rank the following dienophile in order of increasing reactivity in a Diels-Alder reaction, listing the least reactive first.

A) I < II < III

B) III < I < II

C) II < I < III

D) III < II < I

26) Which of the following compounds is the least reactive dienophile in a Diels-Alder reaction?

A) I

B) II

C) III

D) IV

27) Which of the following compounds is the most reactive dienophile in a Diels-Alder reaction?

A) I

B) II

C) III

D) IV

28) Which of the following is the most reactive diene in a Diels-Alder reaction?

A) I

B) II

C) III

D) IV

29) Which of the following is the least reactive diene in a Diels-Alder reaction?

A) I

B) II

C) III

D) IV

30) What is the major organic product of the following reaction?

A) I

B) II

C) III

D) IV

31) What is the major organic product of the following reaction?

A) Only I

B) Only II

C) Only III

D) Only I and II

32) What is the major organic product of the following reaction?

A) Only I

B) Only II

C) Only III

D) Only I and II

33) What is the major organic product of the following reaction?

A) Only I

B) Only I and II

C) Only II and III

D) I, II, and III

34) What is the major organic product of the following reaction?

A) I

B) II

C) III

D) IV

35) What is the major organic product of the following reaction?

A) I

B) II

C) III

D) IV

36) What diene and dienophile are used in a Diels-Alder reaction to prepare the following compound?

A) I

B) II

C) III

D) IV

37) Which of the following compound absorbs UV light at the longest wavelength?

A) I

B) II

C) III

D) IV

38) Which of the following compound absorbs UV light at the longest wavelength?

A) I

B) II

C) III

D) IV

39) Which of the following electronic transitions is common in the UV spectrum of 1,3-butadiene?

A) s®p

B) s®p*

C) n ®p*

D) p®p*

40) What is the definition of a resonance structure?

A) Compounds with the same molecular formula

B) Compounds with different carbon frameworks

C) Structures that differ only in the placement of π and nonbonding electrons

D) Structures that differ only in the location of bonds

41) Rank the following anions from most to least stable, listing the most stable first.

A) I> II > III

B) III > II > I

C) I > III > II

D) III > I > II

42) How would you favor the formation of the kinetic product of the following reaction?

A) Excess HBr

B) Long reaction time

C) Low temperature

D) High pressure

43) Which of the following is an example of a bridged bicyclic system?

A) I

B) II

C) III

D) IV

44) Why would the compound below not react with a dienophile in a Diels-Alder reaction?

A) The compound is not a conjugated diene.

B) There are no electron withdrawing groups on the compound.

C) There are no electron donating groups on the compound.

D) The compound cannot adopt the s-cis conformation.

45) Which of the following is not a resonance structure of acetic anhydride?

A) I

B) II

C) III

D) IV

46) Which triene has the largest heat of hydrogenation?

A) I

B) II

C) III

D) IV

47) Which triene has the smallest heat of hydrogenation?

A) I

B) II

C) III

D) IV

48) Which triene absorbs the longest wavelength of UV light?

A) I

B) II

C) III

D) IV

49) Which of the following is a major resonance contributor to the first structure?

A) I

B) II

C) III

D) IV

50) What is the major product of the following reaction?

A) I

B) II

C) III

D) IV

51) What is the major product of the following reaction?

A) I

B) II

C) III

D) IV

52) What is the major product of the following reaction?

A) I

B) II

C) III

D) IV

53) What is the major product of the following reaction?

A) I

B) II

C) III

D) IV