Package Title: Solomons Test Bank Course Title: Solomons 11e Chapter Number: 13 Question type: Multiple choice 1) The allyl radical has how many bonding
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[Show More] π molecular orbitals? a) 1 b) 2 c) 3 d) 4 e) 5 Answer: A Topic: Molecular Orbitals Section: 13.2 Difficulty Level: Medium 2) The allyl radical has how many electrons in bonding π molecular orbitals? a) 1 b) 2 c) 3 d) 4 e) 5 Answer: B Topic: Molecular Orbitals Section: 13.2 Difficulty Level: Medium 3) The allyl radical has how many electrons in non-bonding π molecular orbitals? a) 1 b) 2 c) 3 d) 4 Contact: royfields212@gmail.com e) 5 Answer: A Topic: Molecular Orbitals Section: 13.2 Difficulty Level: Medium 4) The allyl radical has how many π molecular orbitals? a) 1 b) 2 c) 3 d) 4 e) 5 Answer: C Topic: Molecular Orbitals Section: 13.2 Difficulty Level: Medium 5) The HOMO of the allylic radical has how many electrons in its ground state? a) 1 b) 2 c) 3 d) 4 e) 0 Answer: A Topic: Molecular Orbitals Section: 13.2 Difficulty Level: Medium 6) The LUMO of the allylic radical has how many electrons in its ground state? a) 1 b) 2 c) 3 d) 4 e) 0 Answer: E Topic: Molecular Orbitals Section: 13.2 Difficulty Level: Medium 7) The HOMO of the allylic cation has how many electrons in its ground state? a) 1 b) 2 c) 3 d) 4 e) 0 Answer: B Topic: Molecular Orbitals Section: 13.2 Difficulty Level: Medium 8) The allyl cation has how many electrons in bonding π molecular orbitals? a) 1 b) 2 c) 3 d) 4 e) 5 Answer: B Topic: Molecular Orbitals Section: 13.3 Difficulty Level: Medium 9) The allyl cation has how many bonding π molecular orbitals? a) 1 b) 2 c) 3 d) 4 e) 5 Answer: A Topic: Molecular Orbitals Section: 13.3 Difficulty Level: Medium 10) The allyl cation has how many π molecular orbitals? a) 1 b) 2 c) 3 d) 4 e) 5 Answer: C Topic: Molecular Orbitals Section: 13.3 Difficulty Level: Medium 11) 1,3-Pentadiene has how many bonding π molecular orbitals? a) 1 b) 2 c) 3 d) 4 e) 0 Answer: B Topic: Molecular Orbitals Section: 13.6 Difficulty Level: Medium 12) 1,3-butadiene has how many bonding π molecular orbitals? a) 1 b) 2 c) 3 d) 4 e) 0 Answer: B Topic: Molecular Orbitals Section: 13.6 Difficulty Level: Medium 13) 1,3-Pentadiene has how many antibonding π molecular orbitals? a) 1 b) 2 c) 3 d) 4 e) 0 Answer: B Topic: Molecular Orbitals Section: 13.7 Difficulty Level: Medium 14) 1,3-butadiene has how many electrons in its ground state bonding π molecular orbitals? a) 1 b) 2 c) 3 d) 4 e) 0 Answer: D Topic: Molecular Orbitals Section: 13.6 Difficulty Level: Medium 15) 1,3-butadiene has how many electrons in its ground state antibonding π molecular orbitals? a) 1 b) 2 c) 3 d) 4 e) 0 Answer: E Topic: Molecular Orbitals Section: 13.6 Difficulty Level: Medium 16) The HOMO of 1,3-pentadiene has how many electrons in its ground state? a) 1 b) 2 c) 3 d) 4 e) 0 Answer: B Topic: Molecular Orbitals Section: 13.6 Difficulty Level: Medium 17) The LUMO of 1,3-pentadiene has how many electrons in its ground state? a) 1 b) 2 c) 3 d) 4 e) 0 Answer: E Topic: Molecular Orbitals Section: 13.6 Difficulty Level: Medium 18) The HOMO of 1,3-pentadiene has how many electrons in its excited state? a) 1 b) 2 c) 3 d) 4 e) 0 Answer: A Topic: Molecular Orbitals Section: 13.6 Difficulty Level: Medium 19) The LUMO of 1,3-pentadiene has how many electrons in its excited state? a) 1 b) 2 c) 3 d) 4 e) 0 Answer: E Topic: Molecular Orbitals Section: 13.6 Difficulty Level: Medium 20) Which carbocation would be least stable? a) I b) II c) III d) IV e) V Answer: E Topic: Stability (Alkenes, Cations, Radicals) Section: 13.3 Difficulty Level: Easy 21) Which carbocation would be least stable? a) I b) II c) III d) IV e) V Answer: B Topic: Stability (Alkenes, Cations, Radicals) Section: 13.3 Difficulty Level: Easy 22) Which carbocation would be most stable? a) I b) II c) III d) IV e) V Answer: A Topic: Stability (Alkenes, Cations, Radicals) Section: 13.3 Difficulty Level: Easy 23) Which carbocation would be most stable? a) b) c) d) e) Answer: C Topic: Stability (Alkenes, Cations, Radicals) Section: 13.3 Difficulty Level: Easy 24) Which carbocation would be least stable? a) b) c) d) e) Answer: D Topic: Stability (Alkenes, Cations, Radicals) Section: 13.3 Difficulty Level: Easy 25) Which carbocation would be most stable? a) I b) II c) III d) IV e) V Answer: C Topic: Stability (Alkenes, Cations, Radicals) Section: 13.3 Difficulty Level: Easy 26) Which carbocation would be most stable? a) I b) II c) III d) IV e) V Answer: C Topic: Stability (Alkenes, Cations, Radicals) Section: 13.3 Difficulty Level: Easy 27) Which of the following dienes would you expect to be the most stable? a) CH3CH=CHCH=CHCH3 b) CH3CH=CHCH2CH=CH2 c) CH2=CHCH2CH2CH=CH2 d) CH2=CHCH(CH3)CH=CH2 e) CH3CH=C=CHCH2CH3 Answer: A Topic: Stability (Alkenes, Cations, Radicals) Section: 13.8 Difficulty Level: Easy 28) Which of the following dienes would you expect to be the most stable? a) CH3CH2CH=CHCH2CH=CHCH3 b) CH3CH=CHCH=CHCH2CH3 c) CH2=CHCH2CH2CH2CH=CH2 d) CH2=CHCH=CHCH2CH2CH3 e) CH3CH2CH=C=CHCH2CH3 Answer: B Topic: Stability (Alkenes, Cations, Radicals) Section: 13.7 Difficulty Level: Easy 29) Which of the following compounds would be the most stable? a) I b) II c) III d) IV e) They are all of equal stability. Answer: A Topic: Stability (Alkenes, Cations, Radicals) Section: 13.7 Difficulty Level: Easy 30) Which diene would be least stable? a) I b) II c) III d) IV e) V Answer: C Topic: Stability (Alkenes, Cations, Radicals) Section: 13.7 Difficulty Level: Easy 31) Which of the following dienes would you expect to be the most stable? a) CH3CH2CH=CHCH2CH=CHCH3 b) CH3CH=CHCH=CHCH2CH3 c) CH2=CHCH2CH2CH2CH=CH2 d) CH2=CHCH=CHCH2CH2CH3 e) CH3CH=C(CH3)CH=CHCH2CH3 Answer: E Topic: Stability (Alkenes, Cations, Radicals) Section: 13.7 Difficulty Level: Medium 32) Which of the following dienes would you expect to be the least stable? a) CH3CH2CH=CHCH2CH=CHCH3 b) CH3CH=CHCH=CHCH2CH3 c) CH2=CHCH2CH2CH2CH=CH2 d) CH2=CHCH=CHCH2CH2CH3 e) CH3CH=C(CH3)CH=CHCH2CH3 Answer: C Topic: Stability (Alkenes, Cations, Radicals) Section: 13.7 Difficulty Level: Medium 33) Considering both configurational and conformational factors, select the most stable form of 2,4-hexadiene. a) I b) II c) III d) IV e) V Answer: A Topic: Stability (Alkenes, Cations, Radicals) Section: 13.7 Difficulty Level: Medium 34) Considering both configurational and conformational factors, select the least stable form of 2,4-hexadiene. a) I b) II c) III d) IV e) V Answer: E Topic: Stability (Alkenes, Cations, Radicals) Section: 13.7 Difficulty Level: Medium 35) Which alkene would you expect to be most stable? a) CH2=CHCH2CH2CH=CH2 b) c) d) e) Answer: E Topic: Stability (Alkenes, Cations, Radicals) Section: 13.7 Difficulty Level: Medium 36) Arrange these hexadienes in order of expected decreasing stability. a) V > II > I > III > IV b) III > IV > II > I > V c) IV > III > II > V > I d) IV > III > I > II > V e) I > II > IV > III > V Answer: D Topic: Stability (Alkenes, Cations, Radicals) Section: 13.7 Difficulty Level: Medium 37) Arrange these hexadienes in order of expected increasing stability. a) V < II < I < III < IV b) III < IV < II < I < V c) IV < III < II < V < I d) IV < III < I < II < V e) I < II < IV < III < V Answer: A Topic: Stability (Alkenes, Cations, Radicals) Section: 13.7 Difficulty Level: Medium 38) Arrange these carbocations in order of expected increasing stability. a) V < II < I < IV < III b) V<I<II<IV<III c) IV <I< II <V< III d) IV < III < I < II < V e) I < II < IV < III < V Answer: B Topic: Stability (Alkenes, Cations, Radicals) Section: 13.3 Difficulty Level: Medium 39) Arrange these carbocations in order of expected increasing stability. a) V < II < I < IV < III b) V<I<II<IV<III c) IV <I< II <V< III d) IV < III < I < II < V e) II < III < IV < V < I Answer: E Topic: Stability (Alkenes, Cations, Radicals) Section: 13.3 Difficulty Level: Medium 40) Which is not an example of resonance? a) I b) II c) III d) IV e) None of these choices are examples of resonance. Answer: C Topic: Resonance Section: 13.4 Difficulty Level: Easy 41) Which is not an example of resonance? a) I b) II c) III d) IV e) None of these choices are examples of resonance. Answer: C Topic: Resonance Section: 13.4 Difficulty Level: Easy 42) Which is not a proper resonance structure for 1,3-butadiene? a) CH2=CH–CH=CH2 b) c) d) e) All of these answer choices are correct. Answer: B Topic: Resonance Section: 13.4 Difficulty Level: Easy 43) Which pair does not represent a pair of resonance structures? a) I b) II c) III d) IV e) All of these choices represent pairs of resonance structures. Answer: D Topic: Resonance Section: 13.4 Difficulty Level: Easy 44) Which pair does not represent a pair of resonance structures? a) I b) II c) III d) IV e) All of these choices represent pairs of resonance structures. Answer: D Topic: Resonance Section: 13.4 Difficulty Level: Easy 45) Which pair does not represent a pair of resonance structures? a) I b) II c) III d) IV e) All of these choices represent pairs of resonance structures. Answer: D Topic: Resonance Section: 13.4 Difficulty Level: Easy 46) Which pair does not represent a pair of resonance structures? a) I b) II c) III d) IV e) All of these choices represent pairs of resonance structures. Answer: D Topic: Resonance Section: 13.4 Difficulty Level: Easy 47) Which pair does not represent a pair of resonance structures? a) I b) II c) III d) IV e) All of these choices represent pairs of resonance structures. Answer: E Topic: Resonance Section: 13.4 Difficulty Level: Easy 48) Which pair does not represent a pair of resonance structures? a) I b) II c) III d) IV e) All of these choices represent pairs of resonance structures. Answer: E Topic: Resonance Section: 13.4 Difficulty Level: Easy 49) Which pair does not represent a pair of resonance structures? a) I b) II c) III d) IV e) All of these choices represent pairs of resonance structures. Answer: E Topic: Resonance Section: 13.4 Difficulty Level: Easy 50) Select the structure of the conjugated diene. a) I b) II c) III d) IV e) V Answer: B Topic: Alkene Classification Section: 13.5 Difficulty Level: Easy 51) Select the structure of the conjugated diene. a) I b) II c) III d) IV e) V Answer: C Topic: Alkene Classification Section: 13.5 Difficulty Level: Easy 52) Select the structure of the conjugated diene. a) I b) II c) III d) IV e) V Answer: C Topic: Alkene Classification Section: 13.6 Difficulty Level: Easy 53) Select the structure of the isolated diene. a) I b) II c) III d) IV e) V Answer: D Topic: Alkene Classification Section: 13.5 Difficulty Level: Easy 54) Select the structure(s) of the conjugated diene(s). a) I and II b) II and III c) III and IV d) I, II and V e) V Answer: C Topic: Alkene Classification Section: 13.5 Difficulty Level: Easy 55) Which of the following dienes is a cumulated diene? a) CH2=CHCH2CH2CH=CH2 b) CH2=CHCH=CHCH2CH3 c) CH3CH=C=CHCH2CH3 d) CH3CH=CHCH=CHCH3 e) CH3CH=CHCH2CH=CH2 Answer: C Topic: Alkene Classification Section: 13.5 Difficulty Level: Easy 56) Which of the following dienes is a cumulated diene? a) CH2=CHCH2CH2CH2CH=CH2 b) CH2=CHCH=CHCH2CH2CH3 c) CH3CH=C=CHCH2CH2CH3 d) CH3CH=CHCH=CHCH2CH3 e) CH3CH2CH=CHCH2CH=CH2 Answer: C Topic: Alkene Classification Section: 13.5 Difficulty Level: Easy 57) Select the structure(s) in which the multiple bonds are conjugated. a) I and II b) II and III c) III and IV d) I, II and V e) V Answer: B Topic: Alkene Classification Section: 13.5 Difficulty Level: Medium 58) Select the structure(s) in which the multiple bonds are conjugated. a) I and IV b) II and III c) III and V d) I, II and III e) V Answer: A Topic: Alkene Classification Section: 13.5 Difficulty Level: Medium 59) What is an IUPAC name for a) 2,3-methylhept-2-en-4-yne b) 1,1,3-trimethylhex-3-yn-1-ene c) 1,1,3-trimethyl-3-hexyn-1-ene d) 2,3-dimethyl-2-hepten-4-yne e) 5,6-dimethyl-5-hepten-3-yne Answer: D Topic: Nomenclature Section: 4.5, 4.6 and 13.5 Difficulty Level: Medium 60) A correct IUPAC name of the compound below is: a) 1-Bromo-1-methyl-2,5-cyclohexadiene b) 3-Bromo-3-methyl-1,4-cyclohexadiene c) 6-Bromo-6-methyl-1,4-cyclohexadiene d) 2-Bromo-2-methyl-1,3-cyclohexadiene e) None of these choices. Answer: B Topic: Nomenclature Section: 4.5, 4.6 and 13.5 Difficulty Level: Medium 61) The substituent R on the bicyclic compound shown is considered to be? a) axial b) equatorial c) endo d) exo e) trans Answer: D Topic: Nomenclature Section: 4.5, 4.6, 7.2 and 13.5 Difficulty Level: Medium 62) The substituent R on the bicyclic compound shown is considered to be? a) axial b) equatorial c) endo d) exo e) trans Answer: C Topic: Nomenclature Section: 4.5, 4.6, 7.2 and 13.6 Difficulty Level: Medium 63) The substituent R on the bicyclic compound shown is considered to be? a) axial b) equatorial c) endo d) exo e) trans Answer: D Topic: Nomenclature Section: 4.5, 4.6, 7.2 and 13.5 Difficulty Level: Medium 64) The substituent R on the bicyclic compound shown is considered to be? a) axial b) equatorial c) endo d) exo e) trans Answer: C Topic: Nomenclature Section: 4.5, 4.6, 7.2 and 13.5 Difficulty Level: Medium 65) The substituent R on the bicyclic compound shown is considered to be? a) axial b) equatorial c) endo d) exo e) trans Answer: D Topic: Nomenclature Section: 4.5, 4.6, 7.2 and 13.5 Difficulty Level: Medium 66) The substituent R on the bicyclic compound shown is considered to be? a) axial b) equatorial c) Endo d) Exo e) Trans Answer: C Topic: Nomenclature Section: 4.5, 4.6, 7.2 and 13.5 Difficulty Level: Medium 67) What is an IUPAC name for this triene? a) (2E,4Z,6e)–2,4,6–Nonatriene b) (2Z,4E,6Z)–2,4,6–Nonatriene c) (2E,4Z,6Z)–2,4,6–Nonatriene d) (3Z,5Z,7e)–3,5,7–Nonatriene e) (3Z,5E,7e)–3,5,7–Nonatriene Answer: C Topic: Nomenclature Section: 4.5, 4.6, 7.2 and 13.5 Difficulty Level: Hard 68) What is an IUPAC name for this triene? a) (2E,4Z,6e)–3,4,7,8–tetramethyl-2,4,6–Nonatriene b) (2Z,4E,6e)–3,4,7,8–tetramethyl-2,4,6–Nonatriene c) (2E,4Z,6e)–2,3,6,7–tetramethyl-3,5,7–Nonatriene d) (2E,4Z,6e)– 2,3,6,7–tetramethyl-3,5,7–Nonatriene e) (2E,4E,6e)–3,4,7,8–tetramethyl-2,4,6–Nonatriene Answer: E Topic: Nomenclature Section: 4.5, 4.6, 7.2 and 13.5 Difficulty Level: Hard 69) Which compound would have the shortest carbon-carbon single bond? a) CH3–CH3 b) CH2=CH–CH3 c) HC≡C–C≡CH d) CH2=CH–C≡CH e) CH2=CH–CH=CH2 Answer: C Topic: Bond Lengths Section: 13.6 Difficulty Level: Easy 70) Which compound would have the shortest carbon-carbon single bond? a) CH≡C–CH=CH–CH2–CH3 b) CH2=CH–CH=CH–CH3 c) HC≡C–CH2–C≡C–CH3 d) CH2=CH–C≡C–CH2–CH3 e) CH3–C≡C–C≡C–CH3 Answer: E Topic: Bond Lengths Section: 13.6 Difficulty Level: Easy 71) Which carbon-carbon bond in the following compound would you expect to be shortest? a) I b) II c) III d) IV e) V Answer: A Topic: Bond Lengths Section: 13.6 Difficulty Level: Easy 72) Which carbon-carbon bond in the following compound would you expect to be longest? a) I b) II c) III d) IV e) V Answer: E Topic: Bond Lengths Section: 13.6 Difficulty Level: Easy 73) Which alkene would you expect to have the highest heat of hydrogenation? a) b) c) d) e) Answer: A Topic: Heat of Hydrogenation Section: 13.7 Difficulty Level: Easy 74) Which alkene would you expect to have the smallest heat of hydrogenation? a) CH2=CHCH2CH2CH=CH2 b) c) d) e) Answer: E Topic: Heat of Hydrogenation Section: 13.7 Difficulty Level: Medium 75) Which alkene would you expect to have the smallest heat of hydrogenation? a) b) c) d) e) Answer: E Topic: Heat of Hydrogenation Section: 13.7 Difficulty Level: Medium 76) Which alkene would you expect to have the lowest heat of hydrogenation? a) I b) II c) III d) IV e) V Answer: A Topic: Heat of Hydrogenation Section: 13.7 Difficulty Level: Medium 77) Which alkene would you expect to have the highest heat of hydrogenation? a) I b) II c) III d) IV e) V Answer: D Topic: Heat of Hydrogenation Section: 13.7 Difficulty Level: Medium 78) Which alkene would you expect to have the lowest heat of hydrogenation? a) I b) II c) III d) IV e) V Answer: B Topic: Heat of Hydrogenation Section: 13.7 Difficulty Level: Medium 79) Which alkene would you expect to have the lowest heat of hydrogenation? a) I b) II c) III d) IV e) V Answer: B Topic: Heat of Hydrogenation Section: 13.7 Difficulty Level: Medium 80. Estimate the stabilization energy for 1,3-butadiene using the heats of hydrogenation in Table 1. Table 1. Heats of Hydrogenation for Selected Compounds C o m p o u n d M o l e s H 2 Δ H ( k J m o l - 1 ) 1 - B u t e n e 1 - 1 2 7 1 - P e n t e n e 1 - 1 2 6 1 , 3 - B u t a d i e n e 2 - 2 3 9 t r a n s - 1 , 3 - P e n t a d i e n e 2 - 2 2 6 a) 13 kJ mol-1 b) 15 kJ mol-1 c) 28 kJ mol-1 d) 239 kJ mol-1 e) 112 kJ mol-1 Answer: B Topic: Heat of Hydrogenation Section: 13.7 Difficulty Level: Hard 81. Estimate the stabilization energy for 1,3-pentadiene using the heats of hydrogenation in Table 1. Table 1. Heats of Hydrogenation for Selected Compounds C o m p o u n d M o l e s H 2 Δ H ( k J m o l - 1 ) 1 - B u t e n e 1 - 1 2 7 1 - P e n t e n e t r a n s - 2 - p e n t e n e 1 1 - 1 2 6 - 1 1 5 1 , 3 - B u t a d i e n e 2 - 2 3 9 t r a n s - 1 , 3 - P e n t a d i e n e 2 - 2 2 6 a) 13 kJ mol-1 b) 15 kJ mol-1 c) 28 kJ mol-1 d) 239 kJ mol-1 e) 112 kJ mol-1 Answer: B Topic: Heat of Hydrogenation Section: 13.7 Difficulty Level: Hard 82. Estimate the stabilization energy for 1,3-cyclohhexadiene using the heats of hydrogenation in Table 1. Table 1. Heats of Hydrogenation for Selected Compounds C o m p o u n d M o l e s H 2 Δ H ( k J m o l - 1 ) C y c l o h e x e n e 1 - 1 2 0 1 , 4 - C y c l o h e x a d i e n e 2 - 2 4 0 1 , 3 - C y c l o h e x a d i e n e 2 - 2 3 2 1 , 5 - H e x a d i e n e 2 - 2 5 3 a) 13 kJ mol-1 b) 21 kJ mol-1 c) 8 kJ mol-1 d) 120 kJ mol-1 e) 112 kJ mol-1 Answer: C Topic: Heat of Hydrogenation Section: 13.7 Difficulty Level: Hard 83) Which compound would have a UV absorption band at longest wavelength? a) I b) II c) III d) IV e) V Answer: B Topic: UV-Vis Spectroscopy Section: 13.8 Difficulty Level: Easy 84) Which compound would have a UV absorption band at longest wavelength? a) I b) II c) III d) IV e) V Answer: B Topic: UV-Vis Spectroscopy Section: 13.8 Difficulty Level: Easy 85) Which compound would have a UV absorption band at longest wavelength? a) I b) II c) III d) IV e) V Answer: B Topic: UV-Vis Spectroscopy Section: 13.8 Difficulty Level: Easy 86) Select the most energetically favorable UV transition for 1,3-butadiene. a) n ⎯⎯⎯→ σ* b) n ⎯⎯⎯→ π* c) π2 ⎯⎯⎯→ π3 * d) σ ⎯⎯⎯→ σ* e) π1 ⎯⎯⎯→ π4 * Answer: C Topic: UV-Vis Spectroscopy Section: 13.8 Difficulty Level: Easy 87) Which compound would have a UV absorption band at longest wavelength? a) I b) II c) III d) IV e) V Answer: A Topic: UV-Vis Spectroscopy Section: 13.8 Difficulty Level: Easy 88) Which of these symbols is used in connection with the intensity of absorption in the UVvisible region? a) ∝ b) ν c) ε d) λ e) θ Answer: C Topic: UV-Vis Spectroscopy Section: 13.8 Difficulty Level: Easy 89) Ignoring stereochemistry, the 1:1 reaction of bromine with 1,3-cyclohexadiene at 25°C in the dark and in the absence of peroxide forms which of these? a) I b) II c) III d) IV e) Both I and II Answer: E Topic: Conjugate Addition Reactions Section: 13.9 Difficulty Level: Medium 90) Ignoring stereochemistry, the 1:1 reaction of chlorine with 1,3-cyclohexadiene at 25°C in the dark and in the absence of peroxide forms which of these? a) I b) II c) III d) IV e) Both I and II Answer: E Topic: Conjugate Addition Reactions Section: 13.9 Difficulty Level: Medium 91) Keeping in mind stereochemistry, how many products are formed by the reaction of one equivalent of HBr with 2-methyl-1,3-cyclohexadiene? a) 2 b) 4 c) 6 d) 8 e) 10 Answer: C Topic: Conjugate Addition Reactions Section: 13.9 Difficulty Level: Medium 92) Which of the following dienes might react with bromine in CCl4 to yield 2,5-dibromo-3- hexene? a) CH2=CHCH2CH2CH=CH2 b) CH2=CHCH=CHCH2CH3 c) CH3CH=C=CHCH2CH3 d) CH3CH=CHCH=CHCH3 e) CH3CH=CHCH2CH=CH2 Answer: D Topic: Conjugate Addition Reactions Section: 13.9 Difficulty Level: Medium 93) Indicate which products would be obtained from the chlorination of 1,5-hexadiene at high temperature (500°c), using a 1:1 mole ratio of the reactants. a) I and II b) II and III c) III and IV d) IV and V e) V and I Answer: C Topic: Conjugate Addition Reactions Section: 13.9 Difficulty Level: Medium 94) Which reagent would convert 1,3-pentadiene into 3-penten-2-ol? a) KMnO4/ - OH b) OsO4 c) H2O2, then H3O+ d) Cl2/H2O e) H3O+ Answer: E Topic: 1,2 Reactions of Conjugated Dienes Section: 13.9 Difficulty Level: Medium 95) Which reagent would convert 1,3-octadiene into 3-octen-2-ol? a) KMnO4/ - OH b) OsO4 c) H2O2, then H3O+ d) Cl2/H2O e) H3O+ Answer: E Topic: 1,2 Reactions of Conjugated Dienes Section: 13.9 Difficulty Level: Medium 96) Which is the only compound which can be completely ruled out as a product of the reaction of 1,3-butadiene with HCl? a) (S)-3-chloro-1-butene b) (R)-3-chloro-1-butene c) (e)-1-chloro-2-butene d) (Z)-1-chloro-2-butene e) (Z)-2-chloro-2-butene Answer: E Topic: Conjugate Addition Reactions Section: 13.9 Difficulty Level: Hard 97) How could the following synthesis be carried out? a) (1) Br2/CCl4; (2) CH3CH2MgCl, ether; (3) CH3ONa/CH3OH b) (1) HBr, 80°C; (2) (CH3CH2) 2CuLi, ether c) (1) HBr, 80°C; (2) Mg, ether; (3) CH3CH2OH, then H3O+ d) More than one of these choices. e) All of these choices. Answer: B Topic: Multistep Synthesis Section: 13.9 Difficulty Level: Hard 98) How could the following synthesis be carried out? a) (1) Br2/CCl4; (2) CH3MgCl, ether; (3) CH3ONa/CH3OH b) (1) HBr (1 eq); (2) (CH3) 2CuLi, ether c) (1) HBr (1eq); (2) Li, ether; (3) CuI; (4) CH3Br d) More than one of these choices. e) All of these choices. Answer: C Topic: Multistep Reaction Synthesis Section: 13.9 Difficulty Level: Hard 99) A thermodynamically-controlled reaction will yield predominantly: a) the more/most stable product. b) the product whose formation requires the smallest free energy of activation. c) the product that can be formed in the fewest steps. d) the product that is formed at the fastest rate. e) the product which possesses the greatest potential energy. Answer: A Topic: Reaction Mechanisms and Control Section: 13.9 Difficulty Level: Easy 100) An equilibrium-controlled reaction will yield predominantly: a) the more/most stable product. b) the product whose formation requires the smallest free energy of activation. c) the product that can be formed in the fewest steps. d) the product that is formed at the fastest rate. e) the product which possesses the greatest potential energy. Answer: A Topic: Reaction Mechanisms and Control Section: 13.9 Difficulty Level: Easy 101) A reaction under kinetic (or rate) control will yield predominantly: a) the most stable product. b) the product that can be formed in the fewest steps. c) the product whose formation requires the smallest free energy of activation. d) the product with the greatest potential energy. e) the product with the least potential energy. Answer: C Topic: Reaction Mechanisms and Control Section: 13.9 Difficulty Level: Easy 102) The accompanying diagram, which describes the fate of the intermediate in a reversible reaction, implies that: a) the less stable product forms more rapidly. b) the more stable product forms more rapidly. c) product B will predominate at equilibrium. d) the intermediate has a short lifetime. e) No conclusions can be drawn as to either reaction rate or product stability. Answer: B Topic: Reaction Mechanisms and Control Section: 13.9 Difficulty Level: Medium 103) The accompanying diagram, which describes the fate of the intermediate in a reversible reaction, implies that: a) the less stable product forms more rapidly. b) the more stable product forms more rapidly. c) product B will predominate at equilibrium. d) the intermediate has a short lifetime. e) No conclusions can be drawn as to either reaction rate or product stability. Answer: A Topic: Reaction Mechanisms and Control Section: 13.9 Difficulty Level: Medium 104) The accompanying diagram implies that: a) the formation of B from A would be favored at high temperature. b) the more stable product forms more rapidly from the intermediate species. c) the formation of B from the intermediate is the rate-limiting step in the transformation of A into B d) the formation of B from A is not a concerted reaction. e) All of these statements are true. Answer: E Topic: Reaction Mechanisms and Control Section: 13.9 Difficulty Level: Medium 105) Which is an untrue statement concerning the Diels-Alder reaction? a) The reaction is a syn addition. b) The diene must be in the s-cis conformation to react. c) Most Diels-Alder reactions are reversible. d) Generally, the adduct formed most rapidly is the exo product. e) Electron donating groups on the diene and electron withdrawing groups on the dieneophile favor adduct formation. Answer: D Topic: Diels-Alder Reaction Section: 13.10 Difficulty Level: Easy 106) Which of these dienes can undergo the Diels-Alder reaction? a) b) c) d) e) All of these choices can undergo the Diels-Alder reaction. Answer: A Topic: Diels-Alder Reaction Section: 13.10 Difficulty Level: Easy 107) Which of these dienes can undergo the Diels-Alder reaction? a) b) c) d) e) Answer: B Topic: Diels-Alder Reaction Section: 13.10 Difficulty Level: Easy 108) Which of the following can undergo the Diels Alder reaction? a) I and II b) II and III c) III and IV d) I, II and V e) V Answer: C Topic: Diels-Alder Reaction Section: 13.10 Difficulty Level: Easy 109) From the standpoint of reactivity, which is the poorest choice of dienophile to react with 2,3-dimethyl-1,3-butadiene in a Diels-Alder reaction? a) I b) II c) III d) IV e) V Answer: B Topic: Diels-Alder Reaction Section: 13.10 Difficulty Level: Medium 110) What is the product of the following reaction? a) I b) II c) III d) IV e) V Answer: A Topic: Diels-Alder Reaction Section: 13.10 Difficulty Level: Medium 111) Which would be the best synthesis of the following compound? a) I b) II c) III d) IV e) V Answer: B Topic: Diels-Alder Reaction Section: 13.10 Difficulty Level: Medium 112) Which reaction would produce the following compound? a) I b) II c) III d) IV e) None of these choices. Answer: D Topic: Diels-Alder Reaction Section: 13.10 Difficulty Level: Medium 113) Which reaction would produce the following compound? a) I b) II c) III d) IV e) None of these choices. Answer: C Topic: Diels-Alder Reaction Section: 13.10 Difficulty Level: Medium 114) Which reaction would produce the following compound? a) I b) II c) III d) IV e) None of these choices. Answer: D Topic: Diels-Alder Reaction Section: 13.10 Difficulty Level: Medium 115) Which reaction would produce the following compound? a) I b) II c) III d) IV e) None of these choices. Answer: B Topic: Diels-Alder Reaction Section: 13.10 Difficulty Level: Medium 116) Which reaction would produce the following compound? a) I b) II c) III d) IV e) None of these choices. Answer: D Topic: Diels-Alder Reaction Section: 13.10 Difficulty Level: Medium 117) Which reaction would produce the following compound? a) I b) II c) III d) IV e) None of these choices. Answer: C Topic: Diels-Alder Reaction Section: 13.10 Difficulty Level: Medium 118) Which reaction would produce the following compound? a) I b) II c) III d) IV e) None of these choices. Answer: A Topic: Diels-Alder Reaction Section: 13.10 Difficulty Level: Medium 119) Which reaction would produce the following compound? a) I b) II c) III d) IV e) None of these choices. Answer: B Topic: Diels-Alder Reaction Section: 13.10 Difficulty Level: Medium 120) Which reaction would produce the following compound? a) I b) II c) III d) IV e) None of these choices. Answer: D Topic: Diels-Alder Reaction Section: 13.10 Difficulty Level: Medium 121) Which of the following pairs of compounds could be used as the basis for a Diels-Alder synthesis of the compound shown below? a) I b) II c) III d) IV e) More than one of these choices. Answer: D Topic: Diels-Alder Reaction Section: 13.10 Difficulty Level: Medium 122) Which of the following pairs of compounds could be used as the basis for a Diels-Alder synthesis of the compound shown below? a) I b) II c) III d) IV e) V Answer: A Topic: Diels-Alder Reaction Section: 13.10 Difficulty Level: Medium 123) Which of the following pairs of compounds could be used as the basis for a Diels-Alder synthesis of the compound shown below? a) I b) II c) III d) IV e) V Answer: B Topic: Diels-Alder Reaction Section: 13.10 Difficulty Level: Medium 124) Which of the following pairs of compounds could be used as the basis for a Diels-Alder synthesis of the compound shown below? a) I b) II c) III d) IV e) V Answer: B Topic: Diels-Alder Reaction Section: 13.10 Difficulty Level: Medium 125) does not undergo the Diels-Alder reaction because: a) ring systems cannot function as the diene component. b) it cannot adopt the s-cis conformation. c) it lacks electron-withdrawing groups. d) it lacks strong electron-releasing groups. e) the two double bonds are farther apart than in a non-cyclic conjugated system. Answer: B Topic: Diels-Alder Reaction Section: 13.10 Difficulty Level: Medium 126) does not undergo the Diels-Alder reaction as a diene because: a) ring systems cannot function as the diene component. b) it cannot adopt the s-cis conformation. c) it lacks electron-withdrawing groups. d) it lacks strong electron-releasing groups. e) the two double bonds are farther apart than in a non-cyclic conjugated system. Answer: A Topic: Diels-Alder Reaction Section: 13.10 Difficulty Level: Medium 127) does not undergo the Diels-Alder reaction as a diene because: a) ring systems cannot function as the diene component. b) it cannot adopt the s-cis conformation. c) it lacks electron-withdrawing groups. d) it lacks strong electron-releasing groups. e) the two double bonds are farther apart than in a non-cyclic conjugated system. Answer: B Topic: Diels-Alder Reaction Section: 13.10 Difficulty Level: Medium 128) does not undergo the Diels-Alder reaction as a diene because: a) ring systems cannot function as the diene component. b) it cannot adopt the s-cis conformation. c) it lacks electron-withdrawing groups. d) it lacks strong electron-releasing groups. e) the two double bonds are farther apart than in a non-cyclic conjugated system. Answer: B Topic: Diels-Alder Reaction Section: 13.10 Difficulty Level: Medium 129) does not undergo the Diels-Alder reaction as a diene because: a) ring systems cannot function as the diene component. b) it cannot adopt the s-cis conformation. c) it lacks electron-withdrawing groups. d) it lacks strong electron-releasing groups. e) the two double bonds are further apart than in a non-cyclic conjugated system. Answer: B Topic: Diels-Alder Reaction Section: 13.10 Difficulty Level: Medium 130) Which of these dienes is the most reactive in the Diels-Alder reaction? a) b) c) d) e) Answer: C Topic: Diels-Alder Reaction Section: 13.10 Difficulty Level: Medium 131) Which of the following dieneophiles is most reactive in a Diels-Alder reaction: a) I b) II c) III d) IV e) V Answer: C Topic: Diels-Alder Reaction Section: 13.10 Difficulty Level: Medium 132) Which of the following dieneophiles is most reactive in a Diels-Alder reaction: a) I b) II c) III d) IV e) V Answer: D Topic: Diels-Alder Reaction Section: 13.10 Difficulty Level: Medium 133) Which diene and dienophile would you choose to synthesize the following compound? a) I b) II c) III d) IV e) None of these choices. Answer: C Topic: Diels-Alder Reaction Section: 13.10 Difficulty Level: Medium 134) Which diene and dienophile would you choose to synthesize the following compound? a) I b) II c) III d) IV e) None of these choices. Answer: B Topic: Diels-Alder Reaction Section: 13.10 Difficulty Level: Medium 135) Which diene would be least reactive toward Diels-Alder addition of maleic anhydride? a) I b) II c) III d) IV e) V Answer: E Topic: Diels-Alder Reaction Section: 13.10 Difficulty Level: Medium 136) What would be the product of the following reaction? a) I b) II c) III d) IV e) All of these choices. Answer: C Topic: Diels-Alder Reaction Section: 13.10 Difficulty Level: Medium 137) Which diene and dienophile would you choose to synthesize the following compound? a) I b) II c) III d) IV e) None of these choices. Answer: A Topic: Diels-Alder Reaction Section: 13.10 Difficulty Level: Medium 138) Which of the following would afford a synthesis of the following compound? a) I b) II c) III d) IV e) None of these choices. Answer: D Topic: Diels-Alder Reaction Section: 13.10 Difficulty Level: Medium 139) What is the product of the following Diels-Alder cycloaddition reaction: a) I b) II c) III d) IV e) None of these choices. Answer: D Topic: Diels-Alder Reaction Section: 13.10 Difficulty Level: Medium 140) Which of the following would afford a synthesis of the following compound? a) I b) II c) III d) IV e) None of these choices. Answer: C Topic: Diels-Alder Reaction Section: 13.10 Difficulty Level: Medium 141) Which of the following would afford a synthesis of the following compound? a) I b) II c) III d) IV e) None of these choices. Answer: D Topic: Diels-Alder Reaction Section: 13.10 Difficulty Level: Medium 142) Which of the following would afford a synthesis of the following compound? a) I b) II c) III d) IV e) None of these choices. Answer: C Topic: Diels-Alder Reaction Section: 13.10 Difficulty Level: Medium 143) Which diene would you expect to react most rapidly with maleic anhydride? a) I b) II c) III d) IV e) V Answer: D Topic: Diels-Alder Reaction Section: 13.10 Difficulty Level: Medium 144) Which of these conjugated dienes can undergo a Diels-Alder reaction? a) I b) II c) III d) IV e) V Answer: C Topic: Diels-Alder Reaction Section: 13.10 Difficulty Level: Medium 145) Which of these conjugated dienes can undergo a Diels-Alder reaction? a) I b) II c) III d) IV e) All of these choices. Answer: E Topic: Diels-Alder Reaction Section: 13.10 Difficulty Level: Medium 146) Which of these dienes can undergo a Diels-Alder reaction? a) I and V b) I, II and V c) III d) IV e) III and IV Answer: D Topic: Diels-Alder Reaction Section: 13.10 Difficulty Level: Medium 147) Which diene and dienophile would you choose to synthesize the following compound? a) I b) II c) III d) IV e) None of these choices. Answer: C Topic: Diels-Alder Reaction Section: 13.10 Difficulty Level: Medium 148) Which diene and dienophile would you choose to synthesize the following compound? a) I b) II c) III d) IV e) None of these choices. Answer: B Topic: Diels-Alder Reaction Section: 13.10 Difficulty Level: Medium 149) Which diene and dienophile would you choose to synthesize the following compound? a) I and VI b) II and V c) III and IV d) IV and V e) I and III Answer: E Topic: Diels-Alder Reaction Section: 13.10 Difficulty Level: Medium 150) Which diene and dienophile would you choose to synthesize the following compound? a) I and VI b) II and V c) III and IV d) IV and V e) I and III Answer: A Topic: Diels-Alder Reaction Section: 13.10 Difficulty Level: Medium 151) Which compounds could be used in a Diels-Alder synthesis of a) I and III b) I and IV c) II and III d) II and IV e) I and II Answer: C Topic: Diels-Alder Reaction Section: 13.10 Difficulty Level: Medium 152) Which compounds could be used in a Diels-Alder synthesis of a) I and III b) I and IV c) II and III d) II and IV e) I and II Answer: A Topic: Diels-Alder Reaction Section: 13.10 Difficulty Level: Medium 153) Which compounds could be used in a Diels-Alder synthesis of a) I and III b) I and IV c) II and III d) II and IV e) I and II Answer: A Topic: Diels-Alder Reaction Section: 13.10 Difficulty Level: Medium 154) Which compounds could be used in a Diels-Alder synthesis of a) I and III b) I and IV c) II and III d) II and IV e) I and II Answer: A Topic: Diels-Alder Reaction Section: 13.10 Difficulty Level: Medium 155) Which compounds could be used in a Diels-Alder synthesis of a) I and III b) I and IV c) II and III d) II and IV e) I and II Answer: E Topic: Diels-Alder Reaction Section: 13.10 Difficulty Level: Medium 156) Which compounds could be used in a Diels-Alder synthesis of a) I and III b) I and IV c) II and III d) II and IV e) I and II Answer: E Topic: Diels-Alder Reaction Section: 13.10 Difficulty Level: Medium 157) Which compounds could be used in a Diels-Alder synthesis of a) I and III b) I and IV c) II and III d) II and IV e) I and II Answer: E Topic: Diels-Alder Reaction Section: 13.10 Difficulty Level: Medium 158) Which is the major product of the following reaction? a) I b) II c) III d) IV e) None of these choices. Answer: D Topic: Diels-Alder Reaction Section: 13.10 Difficulty Level: Medium 159) Which is the major product of the following reaction? a) I b) II c) III d) IV e) None of these choices. Answer: A Topic: Diels-Alder Reaction Section: 13.10 Difficulty Level: Medium 160) Which is the major product of the following reaction? a) I b) II c) III d) IV e) V Answer: A Topic: Diels-Alder Reaction Section: 13.10 Difficulty Level: Medium 161) Which is the major product of the following reaction? a) I b) II c) III d) IV e) V Answer: D Topic: Diels-Alder Reaction Section: 13.10 Difficulty Level: Medium 162) Which is the major product of the following reaction? a) I b) II c) III d) IV e) V Answer: C Topic: Diels-Alder Reaction Section: 13.10 Difficulty Level: Medium 163) Which diene and dienophile would you choose to synthesize the following compound? a) I b) II c) III d) IV e) None of these choices. Answer: B Topic: Diels-Alder Reaction Section: 13.10 Difficulty Level: Medium 164) Which of these dienes is the most reactive in the Diels-Alder reaction? a) 1,3-Butadiene b) 1,4-Pentadiene c) 2,3,-Dimethyl-1,3-butadiene d) 1,2-Butadiene e) 1,4-Cyclohexadiene Answer: C Topic: Diels-Alder Reaction Section: 13.10 Difficulty Level: Hard 165) Which of these dienes can undergo the Diels-Alder reaction? a) 1,3-Pentadiene b) 1,4-Pentadiene c) 1,2-Butadiene d) 1,4-Cyclohexadiene e) All of these choices can undergo the Diels-Alder reaction. Answer: A Topic: Diels-Alder Reaction Section: 13.10 Difficulty Level: Hard 166) Which of these dienes can undergo the Diels-Alder reaction? a) 1,2-Heptadiene b) 1,3-Heptadiene c) 1,4-Heptadiene d) 1,5-Heptadiene e) 1,6-Heptadiene Answer: B Topic: Diels-Alder Reaction Section: 13.10 Difficulty Level: Hard 167) How would you synthesize: a) I b) II c) III d) IV e) V Answer: A Topic: Diels-Alder Reaction Section: 13.10 Difficulty Level: Hard Question type: fill-in-the-blank 168) Systems that have a p orbital on an atom adjacent to a double bond are called ___ systems. Answer: conjugated unsaturated Topic: General Section: 13.1 Difficulty Level: Easy 169) The hydrogen atom on a saturated (sp3) carbon adjacent to a double bond is called an ___ hydrogen. Answer: allylic Topic: General Section: 13.1 Difficulty Level: Easy 170) The hydrogen atom on a carbon that is part of a double bond is called a ___ hydrogen. Answer: vinyl or vinylic Topic: General Section: 13.1 Difficulty Level: Easy 171) Allylic radicals are ___ stable than tertiary radicals. Answer: more Topic: General Section: 13.1 Difficulty Level: Easy 172) Vinyl cations are ___ stable than tertiary cations. Answer: less Topic: General Section: 13.3 Difficulty Level: Easy 173) There are three types of polyenes (molecules containing two or more double bonds). They are: ___. Answer: conjugated, cumulated, isolated Topic: General Section: 13.5 Difficulty Level: Easy 174) Polyenes in which single and double bonds alternate along the carbon chain are called ___. Answer: conjugated Topic: General Section: 13.5 Difficulty Level: Easy 175) UV-vis spectroscopy can be used to indicate whether ___ is present. Answer: conjugation Topic: General Section: 13.8 Difficulty Level: Easy 176) When the product distribution for a particular reaction reflects the relative stabilities of the products, the reaction is said to be under ___ control. Answer: thermodynamic Topic: General Section: 13.9 Difficulty Level: Easy 177) When the product distribution for a particular reaction reflects the relative rate at which the products are formed, the reaction is said to be under ___ control. Answer: kinetic Topic: General Section: 13.9 Difficulty Level: Easy 178) A thermodynamically-controlled reaction will yield predominantly: ___. Answer: the more/most stable product. Topic: General Section: 13.9 Difficulty Level: Easy 179) The Diels-Alder reaction is a cycloaddition between a conjugated ___ and a ___. Answer: diene; dienophile Topic: General Section: 13.10 Difficulty Level: Easy 180) Stereochemically speaking, the Diels-Alder reaction is ___ and occurs with ___ of the dienophile stereochemistry. Answer: stereospecific; retention Topic: General Section: 13.10 Difficulty Level: Easy 181) A reaction under kinetic (or rate) control will yield predominantly: ___. Answer: the product whose formation requires the smallest free energy of activation. Topic: General Section: 13.9 Difficulty Level: Medium 182) Conjugated dienes routinely undergo 1,2 and 1,4 addition reactions with a variety of electrophilic reagents; this suggests that ___ are likely intermediates during these reactions. Answer: allylic carbocations Topic: General Section: 13.9 Difficulty Level: Medium Question type: Molecular drawing 183) Draw the structural formula for (R)-5-bromo-2,5-dimethyl-1,3-cyclopentadiene, clearly indicating stereochemical details. Answer: Topic: Nomenclature Section: 4.5, 4.6, 5.7, and 13.5 Difficulty Level: Hard 184) Draw the structural formula for (2E,4Z,6e)–3,4,7,8–tetramethyl-2,4,6–nonatriene, clearly indicating stereochemical details. Answer: Topic: Nomenclature Section: 4.5, 4.6, 7.2 and 13.5 Difficulty Level: Hard 185) Draw the structural formula for (2Z,4Z,6Z)-3,4,8-trimethyl-2,4,6-nonatriene, clearly indicating stereochemical details. Answer: Topic: Nomenclature Section: 4.5, 4.6, 7.2 and 13.5 Difficulty Level: Hard 186) Predict the product(s) of the following reaction: Answer: Topic Conjugate Addition Section: 13.9 Difficulty Level: Medium Question type: fill-in-the-blank 187. During Diels-Alder reactions, when two stereoisomer products, exo and endo, are possible, the ___ product is typically obtained as the major product. Answer: endo Topic: Diels-Alder Reactions Section: 13.10 Difficulty Level: Easy Question type: Essay 188) What reagents would be needed to synthesize the following substance via the Diels-Alder reaction? Give stereochemical details, as relevant. Answer: Topic: Diels-Alder Reaction Section: 13.10 Difficulty Level: Medium 189) Which diene and dienophile would you use to prepare the following molecule using a DielsAlder cycloaddition reaction: Answer: Topic: Diels-Alder Reaction Section: 13.10 Difficulty Level: Medium 190) Which diene and dienophile would you use to prepare the following molecule using a DielsAlder cycloaddition reaction: Answer: Topic: Diels-Alder Reaction Section: 13.10 Difficulty Level: Medium 191) The first step in the total synthesis of synthetic cholesterol involves production of the intermediate structure shown. Which combination of diene and dieneophile will result in its preparation? Answer: Topic: Diels-Alder Reaction Section: 13.10 Difficulty Level: Medium 192) The structure below is an intermediate along the way to the production of synthetic morphine. It is produced through a Diels-Alder cycloaddition reaction. Which combination of diene and dieneophile will result in its preparation? Answer: Topic: Diels-Alder Reaction Section: 13.10 Difficulty Level: Medium 193) What combination of diene and dieneophile can be used to prepare the following compound through a Diels-Alder cycloaddition reaction: Answer: Topic: Diels-Alder Reaction Section: 13.10 Difficulty Level: Medium 194) Predict the product of the following Diels-Alder cycloaddition reaction: Answer: Topic Diels-Alder Reaction Section: 13.10 Difficulty Level: Medium 195) Steroids are naturally occurring polycyclic compounds classified as lipids. The Diels-Alder reaction has been widely used in their preparation. Shown below is a precursor molecule used in a total steroid synthesis. What combination of diene and dieneophile can be used to prepare this compound through the use of a Diels-Alder cycloaddition reaction. Answer: Topic Diels-Alder Reaction Section: 13.10 Difficulty Level: Medium 196) Draw arrows to indicate the electron flow for the following intramolecular Diels-Alder cycloaddition reaction: Answer: Topic: Diels-Alder Mechanism Section: 13.10 Difficulty Level: Hard 197) Draw arrows to indicate electron movement that explains the formation of the products shown for the following retro-Diels-Alder reaction: Answer: Topic: Diels-Alder Mechanism Section: 13.10 Difficulty Level: Hard 198) The compound shown below undergoes a retro-Diels-Alder cycloaddition reaction to yield carbon dioxide and another compound. Predict the structure of the other compound formed. Answer: Topic: Diels-Alder Reaction Section: 13.10 Difficulty Level: Hard 199) The alkaloid colchicine is used in the treatment of gout. The first synthetic colchine involved the preparation of the key intermediate shown. Which combination of diene and dieneophile will result in its preparation? Answer: Topic: Diels-Alder Reaction Section: 13.10 Difficulty Level: Hard 200) Which diene and dienophile would you use to prepare the following molecule using a DielsAlder cycloaddition reaction: Answer: Topic: Diels-Alder Reaction Section: 13.10 Difficulty Level: Hard 201) Complete the following sequence of reactions, giving structural details of all key intermediates. Answer: Topic: Multistep Reactions Section: 13.10 Difficulty Level: Hard 202) Complete the following sequence of reactions, giving structural details of all key intermediates. Answer: Topic: Multistep Reactions Section: 13.10 Difficulty Level: Hard 203) Complete the following sequence of reactions, giving structural details of all key intermediates. Answer: Topic: Multistep Reactions Section: 13.2, 13.10 Difficulty Level: Hard 204) Show the steps and reagents necessary to prepare the following compound. Use retrosynthetic analysis as a tool to guide your synthesis. Answer: Topic: Multistep Reactions/Retrosynthetic Analysis Section: 13.10 Difficulty Level: Hard 205) Show the steps and reagents necessary to prepare the following compound. Use retrosynthetic analysis as a tool to guide your synthesis. Answer: Topic: Multistep Reactions/Retrosynthetic Analysis Section: 13.10 Difficulty Level: Hard 206) Show the steps and reagents necessary to prepare the following compound. Use retrosynthetic analysis as a tool to guide your synthesis. Answer: Topic: Multistep Reactions/Retrosynthetic Analysis Section: 13.10 Difficulty Level: Hard 207) Show the steps and reagents necessary to prepare the following compound. Use retrosynthetic analysis as a tool to guide your synthesis. Answer: Topic: Multistep Reactions/Retrosynthetic Analysis Section: 13.10 Difficulty Level: Hard 208) Show the steps and reagents necessary to prepare the following compound. Use retrosynthetic analysis as a tool to guide your synthesis. Answer: Topic: Multistep Reactions/Retrosynthetic Analysis Section: 13.10 Difficulty Level: Hard 209) Show the steps and reagents necessary to prepare the following compound. Use retrosynthetic analysis as a tool to guide your synthesis. Answer: Topic: Multistep Reactions/Retrosynthetic Analysis Section: 13.10 Difficulty Level: Hard 210) Show the steps and reagents necessary to prepare the following compound. Use retrosynthetic analysis as a tool to guide your synthesis. Answer: Topic: Multistep Reactions/Retrosynthetic Analysis Section: 13.10 Difficulty Level: Hard 211) Show the steps and reagents necessary to prepare the following compound. Use retrosynthetic analysis as a tool to guide your synthesis. Answer: Topic: Multistep Reactions/Retrosynthetic Analysis Section: 13.10 Difficulty Level: Hard 212) Show the steps and reagents necessary to prepare the following compound. Use retrosynthetic analysis as a tool to guide your synthesis. Answer: Topic: Multistep Reactions/Retrosynthetic Analysis Section: 13.10 Difficulty Level: Hard 213) Show the steps and reagents necessary to prepare the following compound. Use retrosynthetic analysis as a tool to guide your synthesis. Answer: Topic: Multistep Reactions/Retrosynthetic Analysis Section: 13.10 Difficulty Level: Hard 214) Show the steps and reagents necessary to prepare the following compound. Use retrosynthetic analysis as a tool to guide your synthesis. Answer: Topic: Multistep Reactions/Retrosynthetic Analysis Section: 13.10 Difficulty Level: Hard 215) Show the steps and reagents necessary to prepare the following compound. Use retrosynthetic analysis as a tool to guide your synthesis. Answer: Topic: Multistep Reactions/Retrosynthetic Analysis Section: 13.10 Difficulty Level: Hard 216) Show the steps and reagents necessary to prepare the following compound. Use retrosynthetic analysis as a tool to guide your synthesis. Answer: Topic: Multistep Reactions/Retrosynthetic Analysis Section: 13.10 Difficulty Level: Hard [Show Less]