SS13 E1 - Practice exam PDF

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CHE 321 Summer 2013

Exam 1

Form 1

Multiple Choice Questions: 50 points 1. Choose the order that has the following contributing structures of carbonic acid correctly arranged with respect to increasing importance (stability).

2. Select the structure(s) that have trigonal pyramidal geometry.

A i

B ii

C iii

D i & ii

E i & iii

F ii & iii

3. Select the order that has the indicated bonds of the following compound correctly arranged with respect to increasing bond length.

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CHE 321 Summer 2013

Exam 1

Form 1

4. Select the two alcohols that you would predict to exhibit similar reactivity towards the following silyl protection reaction (which you will learn later on this semester).

A i & ii

B i & iii

C i & iv

D ii & iii

E ii & iv

F iii & iv

Use the following structure of ibuprofen to solve the next two problems.

5. Select the correct molecular formula of ibuprofen. A C11H14O2

B C12H16O2

C C13H18O2

D C13H20O2

E C14H20O2

6. Choose the interaction that ibuprofen would not exhibit with ethanol (CH3CH2OH). A dispersion

B dipole-dipole

C hydrogen bonding

D ion-dipole

7. Select the major product of the following isotope-exchange reaction.

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8. Choose the order that has the following anions correctly arranged with respect to increasing stability.

9. Select the correct number of constitutional isomers with the molecular formula C5H11Cl.

A 2

B 4

C 5

D 6

E 7

F 8

10. Choose the order that has the following compounds correctly arranged with respect to increasing acidity.

Short Answer Questions: 50 points 11. Draw the Lewis structure of acetate ion (CH3COO-), showing all bonds, electron lone pairs, and any formal charge(s). 5 pts

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12. Draw the structure of the major product of the following acid-base reaction. 5 pts

13. Draw the structure of a compound that meets all of the following criteria. 5 pts a. Has a molecular formula of C6H10O. b. Has exactly 5 sp3 hybridized carbon atoms and 1 sp2 hybridized carbon atom. c. Has an aldehyde functional group.

14. The following mechanistic step is part of a reaction you will learn in organic chemistry II, known as the aldol condensation. Based on the following curved arrows, give the corresponding intermediate formed. 5 pts

15. Draw the next two most important contributing structures of the following cation. 10 pts

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16. Hydride ion is a strong base commonly used to deprotonate alcohols. Use the curved arrow formalism to show the bond breaking and bond making steps of the following reaction sequence. 10 pts

17. Using the library of synthetic reactions on the cover page, propose a synthesis of the following compound from compounds containing four carbon atoms or less. 10 pts

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