Gabriella Fiorino

Exam 5 ReviewNote: I did not include a Malonic ester and acetoacetic ester question. We can do these

during the session, time permitting, but regardless be sure to study it.

1. Choose the best reagent to form the following product

2. What reagent can you use to create CH2=C(OH)CH2CH3 from (CH3)2CHC(O)CH3?

3. What intermediate would be involved in the following mechanism?

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a) Ketob) Enolc) Enolated) Carbinolamine

4. Choose a valid intermediate to the following mechanism

5. What product forms (answer in condensed formula) if you react (CH3)2CHC(O)CH3 with NaOEt, EtOH with heat followed by CH3Cl and finished off with pyridine?

6. Do the mechanism

7. By what type of mechanism do aldol reactions go through? a) Markovnikovb) Anti-markovnikovc) Syn-additiond) Anti-additione) E1

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f) E2g) E1cBh) Sn1i) Sn2

8. Which of the following reactants would be most synthetically useful in performing aldol reactions?

9. Identify the starting aldehyde or ketone needed to make the following compound via an aldol condensation:

10. Do the thing

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11. Do Claisen

12. Do the thing

13. How many new C-C bonds does Robinson annulation form?

14. Hit it with aqueous sodium hydroxide

15.

Have complements, comments, or concerns about the tutoring session? Click the link below to rate your tutor, Gabriella F.! :D It would make her very happy :D https://ucf.qualtrics.com/jfe/form/SV_0jGMQ3pjtwHlzyRReferences:Klien, D.R. (2015). Organic Chemistry: 2ndEd. Wiley: NJ. Print.Smith, J.G.Organic Chemistry 5th edition. McGraw Hill.

Gabriella Fiorino