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Overview of Alcohols Chapter Exam

Exam Instructions:

Choose your answers to the questions and click 'Next' to see the next set of questions. You can skip questions if you would like and come back to them later with the yellow "Go To First Skipped Question" button. When you have completed the practice exam, a green submit button will appear. Click it to see your results. Good luck!

Page 1

Question 1 1. When an organic alcohol undergoes a dehydration reaction under acidic conditions, what functional group is formed?

Question 2 2. In the final step of the acid-promoted dehydration of cyclopentanol, what species acts as a base to pull off a hydrogen from the carbocation intermediate to form the alkene product?

Question 3 3. Why are carbonyl compounds able to be reduced to alcohols?

Question 4 4. Which of the following uses diisobutylaluminum hydride (DIBAH) as a reducing agent to form primary alcohols?

Question 5 5. When an alcohol is exposed to oxidizing conditions using sodium hypochlorite, what type of reaction conditions are usually needed?

Page 2

Question 6 6. In the third mechanistic step of the oxidation of cyclohexanol, what reactive species adds to cyclohexanol and triggers the ejection of water as a leaving group?

Question 7 7. Why can't alcohol's undergo halide substitution reactions without a preparation first?

Question 8 8. What types of reaction will primary alcohols undergo with HBr?

Question 9 9. What product is formed by using a Grignard reaction?

Question 10 10. Why are Grignard reagents important to a Grignard reaction?

Page 3

Question 11 11. What important reaction has to happen in the first step of an alcohol alkylation mechanism?

Question 12 12. Of the compounds below, which one represents an alcohol that has been alkylated (i.e. which one is an ether)?

Question 13 13. What is the name of this alcohol?

Question 14 14. What is the name of this alcohol?

Question 15 15. What is the name of this alcohol?

Page 4

Question 16 16. What type of alcohol is this?

Question 17 17. What is the primary function of an acid catalyzed hydration?

Question 18 18. What molecule, used during the acid catalyzed hydration, is never consumed at the end of the reaction?

Question 19 19. Classify the following alkyl halide.

Question 20 20. Which of the following molecules is a nucleophile?

Page 5

Question 21 21. Which of the following is not true about isopropyl alcohol?

Question 22 22. What is the chemical structure of isopropyl alcohol?

Question 23 23. Phenol can be made using _____ and _____.

Question 24 24. Which of the following reagents would you use to deprotonate phenol?

Question 25 25. The structure of hexanol is shown below. Which of the following functional groups can be identified in this structure?

Page 6

Question 26 26. What is the correct molecular formula for alcohol?

Question 27 27. What is the correct term of the reactive intermediate that forms when the water molecule pops off of the cyclopentane ring?

Question 28 28. Which of the following can be reduced to form secondary alcohols?

Question 29 29. When a secondary alcohol is oxidized with sodium hypochlorite the product is always a _____.

Question 30 30. What is the missing intermediate (question mark 'b') in this reaction?

Overview of Alcohols Chapter Exam Instructions

Choose your answers to the questions and click 'Next' to see the next set of questions. You can skip questions if you would like and come back to them later with the yellow "Go To First Skipped Question" button. When you have completed the practice exam, a green submit button will appear. Click it to see your results. Good luck!

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