CHM-232 Topic 1 Quiz Spring 2024 Version A PDF

## CHM-232 Topic 1 Quiz spring 2024 Version A **Directions:** Answer each of the following problems/questions. Each problem/question is worth 1.5 points. Problem/Questions are shown one at a time. You can go back to questions. The quiz has a total of 45 points available; five points extra credit. T...

## CHM-232 Topic 1 Quiz spring 2024 Version A **Directions:** Answer each of the following problems/questions. Each problem/question is worth 1.5 points. Problem/Questions are shown one at a time. You can go back to questions. The quiz has a total of 45 points available; five points extra credit. The time limit is 80 minutes. - **Br₂ or NBS** - **UV** - **HO** - **OH** - **R** - **R** - **O₂₀, H₂O₁** - **H₂** - **Pd, Pt, Raney Ni** - **R** - **R** - **R** - **R** - **NaNH₂** - **Off** - **R** - **Br** - **R** - **OH** - **MCPBA or RCO₂H** - **R** - **R** - **Br** - **R** - **OH** - **R** - **R** - **CH₂CH₂** - **R** - **R** - **R** - **R** - **OH** - **H₂** - **Lindlar's** - **R** - **R** - **R** - **R** - **HO** - **OH** - **R** - **R** - **H₃PO₄** - **H₂SO₄ Δ** - **R** - **R** - **H₂O** - **R** - **KMnO₄** - **R** - **"R"** - **R** - **R** - **R** - **R** - **R** - **HO₂ or H₂O₂** - **R** - **R** - **R** - **R** - **OH R** - **OH** - **H₂O** - **R** - **R** - **H₂** - **Pd, Pt, Raney Ni** - **R** - **R** - **R** - **R** - **R** - **NaNH₂ or NaH** - **R** - **R** - **R** - **CNa** - **Br** - **HBr** - **R** - **R** - **R** - **(CH₃)₂S** - **R** - **R** - **R** - **H** - **R** - **¹ SiaBH₄** - **R** - **R** - **² NaOH, H₂O₂** - **H** - **HBr, H₂O₂** - **Br** - **CH₂** - **R** - **R** - **R** - **Zn(Cu)** - **R** - **¹ Hg(OAc)₂** - **R** - **OH or OR** - **R** - **HgSO₄, H₂SO₄** - **H₂O** - **R** - **H₂O or R'OH** - **R** - **KMnO₄** - **² NaBH₄** - **R** - **¹ BH₃, THF** - **R** - **OH** - **CH₂** - **R-Na** - **R** - **WOH** - **² NaOH, H₂O₂** - **R** - **0⁻ -** - **² H** - **R(H)** - **¹ BH₃. THF** - **R** - **OH** - **CH₂** - **R** - **R** - **"R" (H)** - **¹ BH₃, THF** - **R** - **OH** - **CH₂** - **R** - **² NaOH, H₂O₂** - **R** - **0⁻ -** - **2 H** - **R(H)** **1. What is the IUPAC name for the following molecule?** - **Br** - **OH** - **H₃C** - **CH₃** **a. (R,Z)-8-bromonona-7-en-4-yn-2-ol** **b. (S,Z)-8-bromonona-7-en-4-yn-2-ol** **c. (S,E)-2-bromonona-2-en-5-yn-8-ol** **d. (R,E)-2-bromonona-2-en-5-yn-8-ol** **e. (S,E)-1-bromo-1,7-dimethylhept-1-en-4-yn-7-ol** **f. (R,Z)-7-bromo-1,7-dimethylhept-6-en-3-yn-1-ol** * a * b * c * d * e * f ## CHM-232 Topic 1 Quiz spring 2024 Version A **2. Match the bond and the correct description.** 1. mi**ale** bond i Shortest bond 2. lungst bond ii Middle 3. Shirkst bond iii Longest bond **3. Select the intermediates that appear in the mechanism for the reaction shown in the box.** - **HCCH₂** - **HOI** - **excess** - **Cl** **I.** **II.** **III.** **IV.** **V.** * [] I * [] II * [] III * [] IV * [] V **4. A mixture of 1-octyne, 2-octyne, 3-octyne, and 4-octyne was treated with H₂ and PtO₂ in acetic acid. How many products are expected at the completion of the reaction?** * [] 1 * [] 2 * [] 3 * [] 4 **5. Match the intermediate(s) and product with structures for the mechanism of the reaction shown in the box.** - **Br** - **C₄H₆BrO** - **HO¹** **1st intermediate 1.** **2nd intermediate 2.** **product 3.** **6. Match the compound with the correct description.** - **sodium methoxide 1. Strongest base** - **sodium acetylide 2. 2nd strongest base** - **sodium amide 3. 3rd strongest base** - **ammonia 4. Weakest base** **7. Match the compound with the correct description** - **acetylene 1. Strongest acid** - **methane 2. 2nd strongest acid** - **ammonia 3. 3rd strongest acid** - **methanol 4. Weakest acid** **8. An unknown compound has the molecular formula C₆H₁₀. The IR, ¹H-NMR, and ¹³C-NMR of the unknown are shown below. Determine the structure of the unknown.** * [] a * [] b * [] c * [] d * [] e **9. For the following reaction, which of the following describes the product?** - **H₂C** - **CH** - **H₃C** - **i. H₂, Lindlar catalyst** - **ii. Br₂, CCl₄** - **?** **a. A pair of enantiomers will be produced.** **b. A single diastereomer will be produced.** **c. A mixture of diastereomers will be produced.** **d. A meso compound will be produced.** **e. The product will be achiral.** * [] a * [] b * [] c * [] d * [] e **1. An alkyne is hydrated to produce a ketone.** **In the reaction, an enol intermediate forms which then tautomerizes to the final ketone product. Which of the following is mechanistic intermediate in the tautomerization in this reaction?** **A.** **B.** **C.** **D.** **E.** **11. Select the structure that is an intermediate for the tautomerization shown.** - **OH** - **KOH, H₂O** - **E** **A.** **B.** **C.** **D.** **E.** **12. An alkyne is reduced to a trans alkene as shown in the box. Match the step and the description of that step for the mechanism of this reaction.** - **Na** - **NH₃** - **step i** - **step ii** - **step iii** - **step iv** **1. electron transfer** **2. protonation** **13. Terminal alkynes such as 1-butyne (A) can be isomerized to more stable internal alkynes (2-butyne; E) when treaed with aqueous potassium hydroxide as shown below. How many curved arrows are needed to complete the mechanism?** **Mechanism** - **CH₃** - **H** - **H-C≡C-C** - **CH₃** - **H** - **step 1** - **H-C=C=C** - **H** - **step 2** - **CH₃** - **H** - **H-C=CEC-CH3** - **H** - **step 3** - **CH₃** - **H** - **CH-C≡C-C** - **H** - **step 4** - **H₃C** - **H** - **H₃C-C≡C-CH₃** * [] 8 * [] 9 * [] 10 * [] 11 * [] 12 **14. Ozonolysis of an unknown compound gave the product shown. Based upon the molecular formula of the unknown and the product shown, what is the name of the unknown?** - **i. O₃** - **ii. (CH₃)₂S** **C₁₀H₁₄** **a. deca-4,6-diyne** **b. deca-2,8-diyne** **c. cyclodeca-1,6-diyne** **d. deca-1,9-dien-5-yne** **e. cyclodeca-1-en-6-yne** **f. None of these choices is correct.** * [] a * [] b * [] c * [] d * [] e * [] f **15. Which of the following syntheses fail to proceed as written?** **I.** **II.** **III.** **IV.** **V.** * [] I * [] II * [] III * [] IV * [] V **16. Match the bond with the correct description.** - **C≡C 1. Largest wave number for the stretching vibration in IR spectrum** - **C=O 2. 2nd Largest wave number for the stretching vibration in IR spectrum** - **C-H 3. 3rd Largest wave number for the stretching vibration in IR spectrum** - **O-H 4. Smallest wave number for the stretching vibration in IR spectrum** **17. Which of the following explains the driving force for enol -> carbonyl tautomerism?** **a. Breaking C-O bond** **b. Breaking O-H bond** **c. Breaking C=C bond** **d. Making C-H bond** **e. Making C=O bond** **18. For the following mechanism, match the step and type of mechanism for that step. A mechanism may be used once, multiple times, or not used.** - **MeO** - **N₂ ** - **MeO-P** - **O** - **H** - **step 1** - **MeO** - **MeO-P** - **O** - **N₂ ** - **+** - **step 2** - **MeO** - **N₂ ** - **MeO-P** - **O** - **R'** - **R** **A.** **B.** **C.** **step 3** - **MeO** - **N₂ ** - **MeO-P** - **O** - **R'** - **R** **D.** **step 4** - **R'** - **C=N₂ ** - **R'** - **C-NEN** - **R'** **E.** **step 5** - **MeO** - **N₂ ** - **MeO-P** - **O** - **R'** **F.** **G.** **step 6** - **¹ Elimination** - **² Addition** - **³ Substitution** - **⁴ Brønsted-Lowry acid-base** - **⁵ Rearrangement** **19. Which reason best explains why Keq > 1 for the following reaction?** - **H-C≡C-CH₃** - **+** - **⁻S-CH₃ ** - **H-C=C-CH₃** - **+** - **⁻S-CH₃** **a. The conjugate base of 2-butyne is a weaker base due to resonance.** **b. The conjugate base of 2-butyne is a stronger base due to resonance.** **c. The conjugate base of 2-butyne is a weaker base due to hybridization.** **d. The conjugate base of 2-butyne is a stronger base due to hybridization.** **20. Match the step with the reagent(s) needed to complete the following synthesis.** - **CH₃ Br** - **step i** - **HC** - **CH** - **Br** - **step ii** - **step iii** - **CH₃** - **H₃C** - **H** **1. 3 equiv. NaNH₂** **2. i. SiaBH₄ ii. NaOH, H₂O₂** **3. H₂O** **4. HgSO₄, H₂O, H₂SO₄** **5. Lindlar catalyst, H₂** **6. excess NaOH** **7. 2 equiv. NaNH₂** **8. 1 equiv. NaNH₂** **9. Na/NH₃** **21. Indicate the number of curved arrows needed.** - **LiO** - **0⁻** - **LiO** - **S=C=S** - **R** - **R** - **step 1** - **R** - **R** **A.** **B.** - **S** - **Me-I** - **step 2** - **S** - **SMe** - **R** - **R** **C.** **D.** - **step 3** - **S** - **R** - **R** - **D** - **step 4** - **(EtO)₃P** - **step 5** - **SMe** - **R** - **R** - **R** - **R** **E.** **F.** - **step 6** - **MeS** - **R** - **R** - **G** - **step 7** - **(EtO)₃P=S** - **R** - **R** - **CO₂** **steps 1-4 4 curved arrows** **steps 5-7 6 curved arrows** **8 curved arrows** **10 curved arrows** **22. Determine compound Y.** - **i. Na/NH₃** - **2-butyne** - **Y** - **ii. Br₂** **a. ** **b. ** **c. ** **d. ** **e. A 1:1 mixture of (b) and (c)** * [] a * [] b * [] c * [] d * [] e **23. Match the step with the reagent(s) needed to complete the following synthesis.** - **?** - **step i** - **step ii** - **step iii** - **step iv** - **OH** - **OH** **1. Na, NH₃** **2. bromoethane** **3. 1-bromopropane** **4. propyne** **5. ethyne** **6. 2-butyne** **7. 1-bromobutane** **8. OsO₄, H₂O₂** **9. 1-butyne** **10. LDA** **11. CH₃CO₂H, H₂O, H⁺** **24. Match the step and the reagent(s) needed to complete the synthesis.** - **step i** - **step ii** - **step iii** - **step iv** - **CH₃** - **3-methyl-1-butene** - **H₃C ** **1. HBr** **2. Br₂, CH₃OOCH₃** **3. CH₂I₂, Zn(Cu)** **4. NaNH₂** **5. acetylene** **6. bromoethane** **7. Br₂** **8. Na, NH₃** **9. sodium acetylide** **10. HBr, CH₃OOCH₃** **25. Match the step and the reagent needed to complete the synthesis.** - **?** - **step i** - **step ii** - **step iii** - **HO** - **CH₃** - **H₃C** **1. HgSO₄, H₂O, H₂SO₄** **2. sodium acetylide** **3. 1-hexyne** **4. acid work-up** **5. 3-hexyne** **6. NaOH** **7. Na, NH₃** **8. 2-hexyne** **26. When alkynes are treated with sodium metal, Na, in liquid ammonia, sodium acts as a:** **a. Brønsted-Lowry acid.** **b. Brønsted-Lowry base.** **c. reducing agent.** **d. oxidizing agent.** **e. catalyst.** * [] a * [] b * [] c * [] d * [] e **27. Match the step and the reagent(s) needed to complete the synthesis.** - **CH₃** - **step i** - **step ii** - **step iii** - **step iv** **1. H₂, Lindlar** **2. excess HBr, CH₃OOCH₃** **3. benzylbromide** **4. 1 equiv. NaNH₂** **5. excess Br₂, CH₃OOCH₃** **6. excess HBr** **7. 3 equiv. NaNH₂** **8. Na, NH₃** **9. excess Br₂** **10. H₂PtO₂, AcOH** **11. bromobenzene** **12. 2 equiv. NaNH₂** **28. Predict the major product for the following reaction.** - **OTS** - **OH** - **sodium acetylide** - **?** - **OH** - **OH** **a. ** **b. ** **c. ** **d. ** **e. ** * [] a * [] b * [] c * [] d * [] e **29. For the following mechanism, determine the number of curved arrows for the indicated steps.** - **MeO** - **N₂ ** - **MeO-P** - **O** - **H** - **step 1** - **MeO** - **MeO-P** - **O** - **N₂ ** - **+** - **step 2** - **MeO** - **N₂ ** - **MeO-P** - **O** - **R'** - **R** **A.** **B.** **C.** **step 3** - **MeO** - **N₂ ** - **MeO-P** - **O** - **R'** - **R** **D.** **step 4** - **R'** - **C=N₂ ** - **R'** - **C-NEN** - **R'** **E.** **step 5** - **MeO** - **N₂ ** - **MeO-P** - **O** - **R'** **F.** **G.** **step 6** - **step 1 through step 3 3 curved arrows** - **step 4 through step 6 4 curved arrows** - **5 curved arrows** - **6 curved arrows** **30. Which of the following explains why Keq > 1 for the following reaction?** - **HC ≡ C-CH₃** - **+** - **⁻OH** - **HC=C-CH₃** - **+** - **⁻OH** **a. The conjugate base of 2-butyne is a weaker base due to resonance.** **b. The conjugate base of 2-butyne is a stronger base due to resonance.** **c. The conjugate base of 2-butyne is a weaker base due to hybridization.** **d. The conjugate base of 2-butyne is a stronger base due to hybridization.** **31. Match the step with the reagent(s) needed to complete the following synthesis.** - **CH₃** - **step i** - **HCCH₂** - **step ii** - **Br** - **step iii** - **CH₃** - **H₃C** - **step iv** - **H** **1. 3 equiv. NaNH₂** **2. i. SiaBH₄ ii. NaOH, H₂O₂** **3. H₂O** **4. HgSO₄, H₂O, H₂SO₄** **5. Lindlar catalyst, H₂** **6. excess NaOH** **7. 2 equiv. NaNH₂** **8. 1 equiv. NaNH₂** **9. Na/NH₃**