Package Title: Solomons Test Bank Course Title: Solomons 11e Chapter Number: 18 Question type: Multiple Choice 1) Which of the compounds listed below is
... [Show More] more acidic than 1-butanol? a) Ethyl acetoacetate b) 2-Butanone c) Ethyl pentanoate d) All of these choices. e) Two of these choices. Answer: A Topic: Relative Acidities Section: 18.1 Difficulty Level: Medium 2) Which of the compounds listed below is more acidic than 1-butanol? a) Diethylmalonate b) 2-Butanone c) Ethyl pentanoate d) All of these choices. e) Two of these choices. Answer: A Topic: Relative Acidities Section: 18.1 Contact: [email protected] Difficulty Level: Medium 3) Which of the compounds listed below is more acidic than 1-butanol? a) Malonic ester b) 2-Butanone c) Ethyl pentanoate d) All of these choices. e) Two of these choices. Answer: A Topic: Relative Acidities Section: 18.1 Difficulty Level: Medium 4) Which of the compounds listed below is more acidic than 1-butanol? a) Ethyl 2-oxocyclohexanecarboxylate b) 2-Butanone c) Ethyl pentanoate d) All of these choices. e) Two of these choices. Answer: A Topic: Relative Acidities Section: 18.1 Difficulty Level: Medium 5) Which of the compounds listed below is more acidic than 2-pentanol? a) Ethyl 3-oxopentanoate b) 2-Pentanone c) Pentanal d) All of these choices. e) Two of these choices. Answer: A Topic: Relative Acidities Section: 18.1 Difficulty Level: Medium 6) Which of the compounds listed below is more acidic than 2-pentanol? a) Diethyl malonate b) 2-Pentanone c) Pentanal d) All of these choices. e) Two of these choices. Answer: A Topic: Relative Acidities Section: 18.1 Difficulty Level: Medium 7) Which of the compounds listed below is more acidic than 2-pentanol? a) Malonic ester b) 2-Pentanone c) Pentanal d) All of these choices. e) Two of these choices. Answer: A Topic: Relative Acidities Section: 18.1 Difficulty Level: Medium 8) Which of the compounds listed below is more acidic than 2-pentanol? a) Ethyl 2-oxocyclohexanecarboxylate b) 2-Pentanone c) Pentanal d) All of these choices. e) Two of these choices. Answer: A Topic: Relative Acidities Section: 18.1 Difficulty Level: Medium 9) Which of the following hydrogens is the most acidic? O O O O I II III IV V a) I b) II c) III d) IV e) V Answer: C Topic: Relative Acidities Section: 18.1 Difficulty Level: Medium 10) Which is the most acidic hydrogen in the compound shown? O O O v V IV I II III a) I b) II c) III d) IV e) V Answer: C Topic: Relative Acidities Section: 18.1 Difficulty Level: Medium 11) Which is the most acidic hydrogen in the compound shown? O O H H H H H H H H H H I II III IV V a) I b) II c) III d) IV e) V Answer: A Topic: Relative Acidities Section: 18.1 Difficulty Level: Medium 12) Which is the most acidic hydrogen in the compound shown? I II III IV V O O O H H H H H H H H H H H a) I b) II c) III d) IV e) V Answer: B Topic: Relative Acidities Section: 18.1 Difficulty Level: Medium 13) Which is the most acidic hydrogen in the compound shown? I II III IV V OH O O H H H H H H H H H a) I b) II c) III d) IV e) V Answer: A Topic: Relative Acidities Section: 18.1 Difficulty Level: Medium 14) Which is the most acidic hydrogen in the compound shown? I II III IV V O H H H H H H H H H C N a) I b) II c) III d) IV e) V Answer: B Topic: Relative Acidities Section: 18.1 Difficulty Level: Medium 15) Which is the most acidic hydrogen in the compound shown? O O H H H H H H H O I II III IV O O H H V a) I b) II c) III d) IV e) V Answer: V Topic: Relative Acidities Section: 18.1 Difficulty Level: Medium 16) Which of the following compounds is the strongest acid? IV I II V III CO2Et O CN CN OH CN CN CN O O a) I b) II c) III d) IV e) V Answer: E Topic: Relative Acidities Section: 18.1 Difficulty Level: Medium 17) Which compound contains the most acidic hydrogens? a) CH3CH2CH3 b) CH3CHCH2 c) Cyclohexane d) (CH3)2C=O e) Benzene Answer: D Topic: Acid/Base Section: 18.1 Difficulty Level: Medium 18) Considering only the highlighted hydrogens, list the following compounds in order of increasing acidity: O O H O H O O O O H H I II III IV V H a) IV,II,III,I,V b) II,V,IV,I,III c) III,I,IV,II,V d) IV,V,II,I,III e) V,IV,III,II,I Answer: D Topic: Acid/Base Section: 18.1 Difficulty Level: Medium 19) Considering only the highlighted hydrogens, list the following compounds in order of decreasing acidity: O O H O H O O O O H H I II III IV V H a) I,II,III,IV,V b) III,V,IV,I,II c) III,I,II,V,IV d) IV,V,II,I,III e) V,IV,III,II,I Answer: C Topic: Acid/Base Section: 18.1 Difficulty Level: Medium 20) Considering only the highlighted hydrogens, list the following compounds in order of increasing acidity: O O H O H H I II III IV V O H O O H a) I,II,III,IV,V b) II,V,III,I,IV c) III,I,IV,II,V d) IV,V,II,I,III e) V,II,III,I,IV Answer: E Topic: Acid/Base Section: 18.1 Difficulty Level: Medium 21) Considering only the highlighted hydrogens, list the following compounds in order of decreasing acidity: O O H O H H I II III IV V O H O O H a) I,II,III,IV,V b) II,V,III,I,IV c) IV,I,III,II,V d) IV,V,II,I,III e) V,IV,III,II,I Answer: C Topic: Acid/Base Section: 18.1 Difficulty Level: Medium 22) Considering only the highlighted hydrogens, list the following compounds in order of increasing acidity: O O H O H H I II III IV V O H O O C N H a) I,II,III,IV,V b) II,V,III,I,IV c) III,I,IV,II,V d) IV,V,II,I,III e) V,II,III,I,IV Answer: E Topic: Acid/Base Section: 18.1 Difficulty Level: Medium 23) Considering only the highlighted hydrogens, list the following compounds in order of decreasing acidity: O O H O H H I II III IV V O H O O C N H a) I,II,III,IV,V b) II,V,III,I,IV c) IV,I,III,II,V d) IV,V,II,I,III e) V,IV,III,II,I Answer: C Topic: Acid/Base Section: 18.1 Difficulty Level: Medium 24) Which structure represents an ester enolate? a) I b) II c) III d) IV e) Two of these choices. Answer: E Topic: Enolates Section: 18.1 Difficulty Level: Medium 25) Which of the following is a keto-enol tautomeric pair? O OH O OH O OH OH O OH O OH and and and and and I II III IV V a) I b) II c) III d) IV e) V Answer: B Topic: Tautomerization and Keto-Enol Equilibrium Section: 18.2 Difficulty Level: Easy 26) Which of the following is a keto-enol tautomeric pair? O and OH O and and OH O OH OH O and OH O and OH I II III IV V a) I b) II c) III d) IV e) V Answer: B Topic: Tautomerization and Keto-Enol Equilibrium Section: 18.2 Difficulty Level: Easy 27) Which of the following is a keto-enol tautomeric pair? O OH O OH and and O OH and O OH and OH O OH and I II III IV V a) I b) II c) III d) IV e) V Answer: A Topic: Tautomerization and Keto-Enol Equilibrium Section: 18.2 Difficulty Level: Easy 28) Which of the following represent tautomers? a) b) c) d) All of these choices. e) None of these choices. Answer: C Topic: Tautomerization and Keto-Enol Equilibrium Section: 18.2 Difficulty Level: Easy 29) Which of these compounds would exist in an enol form to the greatest extent? a) CH3COC2H5 O b) CH3CCH2CCH3 O O c) CH3CCH3 O d) CH3CH O e) CH3CCH2CH2CCH3 O O Answer: B Topic: Tautomerization and Keto-Enol Equilibrium Section: 18.2 Difficulty Level: Easy 30) Which of the following represent keto-enol tautomers? a) CH3CCH2CH3 O CH3C=CHCH3 OH and b) CH3CCH2CH3 O CH2=CCH2CH3 and OH c) CH3CCH2CH3 O HOCH2CCH=CH2 and O d) More than one of these choices. e) None of these choices. Answer: D Topic: Tautomerization and Keto-Enol Equilibrium Section: 18.2 Difficulty Level: Easy 31) Simple enols are less stable than the tautomeric keto forms because: a) severe angle strain exists in the enol forms. b) fewer atoms are coplanar in the keto form. c) the enol cannot be chiral. d) the C-C bond is weaker than the C-O bond. e) Actually, simple enols are the more stable. Answer: D Topic: Tautomerization and Keto-Enol Equilibrium Section: 18.2 Difficulty Level: Medium 32) Which of these compounds would exist primarily in an enol form? a) O b) O O c) O O d) O O e) O O Answer: C Topic: Tautomerization and Keto-Enol Equilibrium Section: 18.2 Difficulty Level: Medium 33) Which of these compounds would exist primarily in an enol form? a) b) c) d) e) Answer: B Topic: Tautomerization and Keto-Enol Equilibrium Section: 18.2 Difficulty Level: Medium 34) Which of these compounds would exist primarily in an enol form? a) O b) O O c) O d) O O e) O O Answer: C Topic: Tautomerization and Keto-Enol Equilibrium Section: 18.2 Difficulty Level: Hard 35) Which of these compounds would exist primarily in an enol form? a) b) c) d) e) Answer: C Topic: Tautomerization and Keto-Enol Equilibrium Section: 18.2 Difficulty Level: Hard 36) Which of the following would undergo racemization in base? C6H5CC6H5 O C CH3CH2CH2 CH3CH2 CH3 CC6H5 O C CH3 CH3CH2 H CC6H5 O C CH3 CH3 CH3 CCH2C6H5 O I II III IV a) I b) II c) III d) IV e) Both III and IV Answer: C Topic: Racemization Section: 18.3 Difficulty Level: Easy 37) Which of the following would undergo epimerization in base? a) I b) II c) III d) IV e) Both III and IV Answer: C Topic: Racemization/Epimerization Section: 18.3 Difficulty Level: Easy 38) Which of the following would undergo epimerization in acid? a) I b) II c) III d) IV e) Both III and IV Answer: C Topic: Racemization/Epimerization Section: 18.3 Difficulty Level: Easy 39) Which of the following would undergo racemization in base? IV I II V III O H3C H O H3C CH3 O H3C CH3 O H O H a) I b) II and III c) IV and V d) I and V e) I, IV and V Answer: D Topic: Racemization Section: 18.3 Difficulty Level: Medium 40) Which of the following would not undergo racemization in base? a) (S)-2-phenylbutanal b) (S)-3-phenylbutanal c) (S)-3-phenyl-2-butanone d) (S)-3-methyl-2-phenylbutanal e) All of these choices will undergo racemization in base. Answer: C Topic: Racemization Section: 18.3 Difficulty Level: Hard 41) Which of these halides is predicted to alkylate malonic ester (as the anion) in highest yield? a) CH3I b) C6H5Br c) (CH3)3CCH2Cl d) CH3CHClCH3 e) All of these choices should be equally effective. Answer: A Topic: Reaction Products Section: 18.7 Difficulty Level: Easy 42) What would be the major product of the following reaction? CCHCH3 O CH3 + Br2 OH- ? CCHCH3 O Br CH3 CCHCH3 O CH3 Br CCBrCH3 O CH3 CCHCH2Br O CH3 CCHCH2Br O CH2Br I II III IV V a) I b) II c) III d) IV e) V Answer: C Topic: Reaction Products Section: 18.3 Difficulty Level: Easy 43) What would be the major product of the following reaction? O + Cl2 -OH ? O Cl O Cl O OH Cl Cl O Cl I II III IV V a) I b) II c) III d) IV e) V Answer: B Topic: Reaction Products Section: 18.3 Difficulty Level: Easy 44) What would be the major product of the following reaction? O + I2 -OH ? O I O I O OH I I O I I II III IV V a) I b) II c) III d) IV e) V Answer: B Topic: Reaction Products Section: 18.3 Difficulty Level: Easy 45) What would be the major product of the following reaction? C6H5CCHCH2CH3 O CH3 + Br2 H3O+ ? a) C6H5CCBrCH2CH3 O CH3 b) C6H5CCHCHCH3 O CH3 Br c) C6H5CCHCHCH3 O CH3 OH d) C6H5CBr2CHCH2CH3 CH3 e) m-BrC6H4CCHCH2CH3 O CH3 Answer: A Topic: Reaction Products Section: 18.3 Difficulty Level: Easy 46) What would be the major product of the following reaction? O + Cl2 H3O + ? O Cl O Cl O OH Cl Cl O Cl I II III IV V a) I b) II c) III d) IV e) V Answer: B Topic: Reaction Products Section: 18.3 Difficulty Level: Easy 47) What would be the major product of the following reaction sequence? O + Br2 H3O + ? O O O Br Br Br Br Br Br OH I II III IV V a) I b) II c) III d) IV e) V Answer: A Topic: Reaction Products Section: 18.3 Difficulty Level: Easy 48) What would be the major product of the following reaction sequence? a) I b) II c) III d) IV e) V Answer: A Topic: Reaction Products Section: 18.3 Difficulty Level: Easy 49) What would be the major product of the following reaction? ODroom temp. ? C6H5C CHCH3 O CH3 + D2O a) C6H5C CHCH3 O CD3 b) C6H5C CDCH3 O CH3 c) CDCH3 CH3 C6D5C O d) CDCD3 CD3 C6H5C O e) C6H5CDCHCH3 OD CH3 Answer: B Topic: Reaction Products Section: 18.3 Difficulty Level: Medium 50) What would be the major product of the following reaction? O D + D2O ? room temperature a) C6H5C CHCH3 O CD3 b) C6H5C CDCH3 O CH3 c) CDCH3 CH3 C6D5C O d) CDCD3 CD3 C6H5C O e) C6H5CDCHCH3 OD CH3 Answer: B Topic: Reaction Products Section: 18.3 Difficulty Level: Medium 51) Which would be formed when 2-methylpropanal is dissolved in D2O containing NaOD? a) CH3CHCD CH3 O b) CH3CHCH CH2D O c) CH3CDCH CH3 O d) CH3CDCD CH3 O e) CH3CHCHOD CH3 D Answer: C Topic: Reaction Products Section: 18.3 Difficulty Level: Medium 52) Which would be formed when 2-methylpropanal is dissolved in T2O containing NaOT? a) b) c) d) e) None of these choices. Answer: C Topic: Reaction Products Section: 18.3 Difficulty Level: Medium 53) Which would be formed when 2-methylpropanal is dissolved in D2O containing D+ ? a) CH3CHCD CH3 O b) CH3CHCH CH2D O c) CH3CDCH CH3 O d) CH3CDCD CH3 O e) CH3CHCHOD CH3 D Answer: C Topic: Reaction Products Section: 18.3 Difficulty Level: Medium 54) What would be the major product of the following reaction? OH O Br2 , PBr3 ? Br O OH O Br Br O Br OH O Br OH HO Br I II III IV V a) I b) II c) III d) IV e) V Answer: C Topic: Reaction Products Section: 18.3 Difficulty Level: Medium 55) Which compound would be formed when 2-methylbutanal is treated with a solution of NaOD in D2O? a) CH3CH2CDCHO CH3 b) CH3CH2CHCDO CH3 c) CH3CHDCHCHO CH3 d) CH2DCH2CHCHO CH3 e) CH3CH2CDCDO CH3 Answer: A Topic: Reaction Products Section: 18.3 Difficulty Level: Medium 56) Which compound would be formed when 2-methylbutanal is treated with a solution of NaOT in T2O? a) b) c) d) e) Answer: A Topic: Reaction Products Section: 18.3 Difficulty Level: Medium 57) Which compound would be formed when 2-methylbutanal is treated with a solution of D+ in D2O? a) CH3CH2CDCHO CH3 b) CH3CH2CHCDO CH3 c) CH3CHDCHCHO CH3 d) CH2DCH2CHCHO CH3 e) CH3CH2CDCDO CH3 Answer: A Topic: Reaction Products Section: 18.3 Difficulty Level: Medium 58) Which compound would be formed when 2,3-dimethylhexanal is treated with a solution of NaOD in D2O? a) O D b) O D D c) O D d) O D e) O D Answer: E Topic: Reaction Products Section: 18.3 Difficulty Level: Medium 59) Which compound would be formed when 2,3-dimethylhexanal is treated with a solution of NaOT in T2O? a) b) c) d) e) Answer: E Topic: Reaction Products Section: 18.3 Difficulty Level: Medium 60) Which compound would be formed when 2,3-dimethylhexanal is treated with a solution of D+ in D2O? a) O D b) O D D c) O D d) O D e) O D Answer: E Topic: Reaction Products Section: 18.3 Difficulty Level: Medium 61) Which of the following would not undergo racemization in base? a) (R)-3-methyl-4-heptanone b) (R)-3-methyl-2-heptanone c) (R)-4-methyl-2-heptanone d) (R)-2,4-dimethyl-3-heptanone e) All of these choices will undergo racemization in base. Answer: C Topic: Racemization Section: 18.3 Difficulty Level: Hard 62) What would be the major product of the following reaction sequence? O + Br2 H3O + O O O Br Br Br Br OH I II III IV V ? -OH heat a) I b) II c) III d) IV e) V Answer: B Topic: Reaction Products Section: 7.6 and 18.3 Difficulty Level: Medium 63) What would be the major product of the following reaction sequence? a) I b) II c) III d) IV e) V Answer: B Topic: Reaction Products Section: 7.6 and 18.3 Difficulty Level: Medium 64) What would be the major product of the following reaction? OH O Br2 , P ? Br O OH O Br Br O Br OH O Br OH HO Br I II III IV V a) I b) II c) III d) IV e) V Answer: C Topic: Reaction Products Section: 18.3 Difficulty Level: Medium 65) What would be the major product of the following reaction sequence? O + Cl2 H3O + ? O Cl O Cl O Cl Cl O Cl I II III IV V -OH heat a) I b) II c) III d) IV e) V Answer: C Topic: Reaction Products Section: 7.6 and 18.3 Difficulty Level: Medium 66) What would be the major product of the following reaction? IV I II V III O O Br HO O Br O O Br O ? i. Br2 , NaOH ii. H3O + a) I b) II c) III d) IV e) V Answer: B Topic: Reaction Products Section: 18.3 Difficulty Level: Medium 67) What would be the major product of the following reaction? IV I II V III O O I HO O I O O I O ? i. I2 , NaOH ii. H3O + a) I b) II c) III d) IV e) V Answer: B Topic: Reaction Products Section: 18.3 Difficulty Level: Medium 68) What would be the major product of the following reaction? OH O i. Br2 , P ii. H2O ? Br O OH O Br Br O Br OH O Br OH HO Br I II III IV V a) I b) II c) III d) IV e) V Answer: B Topic: Reaction Products Section: 18.3 Difficulty Level: Medium 69) What would be the major product of the following reaction? OH O i.Cl2 , P ii. H2O ? Cl O OH O Cl Cl O Cl OH O Cl OH HO Cl I II III IV V a) I b) II c) III d) IV e) V Answer: B Topic: Reaction Products Section: 18.3 Difficulty Level: Medium 70) What would be the major product of the following reaction? a) I b) II c) III d) IV e) V Answer: C Topic: Reaction Products Section: 18.3 Difficulty Level: Medium 71) What would be the major product of the following reaction? a) I b) II c) III d) IV e) V Answer: C Topic: Reaction Products Section: 18.3 Difficulty Level: Medium 72) What would be the major product of the following reaction? OH O Cl2 , P ? Cl O OH O Cl Cl O Cl OH O Cl OH HO Cl I II III IV V a) I b) II c) III d) IV e) V Answer: C Topic: Reaction Products Section: 18.3 Difficulty Level: Medium 73) What would be the major product of the following reaction sequence? IV I II V III O ? i. LDA ii. C2H5 I O O O O a) I b) II c) III d) IV e) V Answer: A Topic: Reaction Products Section: 18.4 Difficulty Level: Medium 74) What would be the major product of the following reaction? IV I II V III O O Cl HO O Cl O O Cl O ? i. Cl2 , NaOH ii. H3O + a) I b) II c) III d) IV e) V Answer: B Topic: Reaction Products Section: 18.3 Difficulty Level: Medium 75) What would be the major product of the following reaction sequence? IV I II V III O ? i. LDA(-78 oC) ii. C2H5OTs O O O O a) I b) II c) III d) IV e) V Answer: A Topic: Reaction Products Section: 18.4 Difficulty Level: Medium 76) What would be the major product of the following reaction sequence? O 1. LDA (-78 oC) 2. CH3CH2Br ? O HO O O O I II III IV V a) I b) II c) III d) IV e) V Answer: C Topic: Reaction Products Section: 18.4 Difficulty Level: Medium 77) What would be the major product of the following reaction sequence? a) I b) II c) III d) IV e) V Answer: C Topic: Reaction Products Section: 18.4 Difficulty Level: Medium 78) What would be the major product of the following reaction sequence?
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