Exam 1

CHEM 210
Questions 1-6: Consider the following steroid used in the treatment of prostate cancer:

Name __________________________

10. Which of the following compounds is the strongest Bronsted-Lowry acid? A. CH3CF2OH B. CF3CH2OH C. CH3CHClOH D. CH3CHFOH E. CCl3CH2OH 11. Which of the following species can be a Lewis acid? A. CH3+ B. AlCl3 C. CH3OCH3 D. AlCl3 and CH3OCH3 E. CH3+ and AlCl3 12. Which of the following compounds is the strongest acid? 1. How many hydrogen atoms are attached to the following carbons? a ______ d ______ g ______ r ______ 2. What is the hybridization of the following atoms? a ______ e ______ c ______ m ______ 3. Name all of the functional groups contained in this molecule (apart from alkane)? __________________________________________ __________________________________________ __________________________________________ __________________________________________ __________________________________________ 4. What are the following bond angles? cda ______ efg ______ d-N-r ______ 5. Rank the following bonds from longest to shortest (ab, c-d, f-g, f-e) ______ ______ ______ ______ longest shortest 6. Rank the following bonds from longest to shortest (k-m, h-j, f-g, N-r): ______ ______ ______ ______ longest shortest 7. Which of the following molecules can hydrogen bond to another molecule identical to itself? A. (CH3)3N B. CH3CH2OCH2CH3 C. CH3SH D. CF3CH3 8. A sulfide should have properties most similar to: A. an alcohol B. an amine C. an ether D. a sulfide E. an alkyl halide 9. Which compound is the strongest Bronsted-Lowry acid? A. H2S B. H2O C. NH3 D. CH4 E. BH3

A. D.

B. E.

C.

13. Which of the following compounds is the weakest acid? A. CH3OH B. CH3OCH3 C. CH3NH2 D. CH3F E. CF3OH

14. Which of the following species is only a Lewis acid? A. A B. B C. C D. B and C E. A, B and C

15. Which of the following species is the strongest base? A. CH3B. NH2C. ClD. OHE. F16. Which anion is the weakest base? A. I
-

B. Br

C. Cl

D. F

17. What is the pKA for a compound with Ka = 102? A. 2-10 B. log 210 C. -200 D. 20 E. -2 18. What is the KA for a compound with pKa = -5? A. 105 B. 5-10 C. -5-10 D. 10-5 E. log 10-5 19. Which pKA indicates the weakest acid? A. KA = 3 x 10-40 B. pKA = 4.7 C. pKA = 15.7 D. KA = 2.1 x 10-5 E. pKA = -1.7 20. Which is the strongest base? A. NH3 B. NH2- C. OHD. H
-

E. F

21. Complete the following chart providing the missing condensed or skeletal structure: tert-butyl alcohol 2-butyn-1-ol Condensed structure CH3CCCH2OH

butanoic acid CH3CH2CH2COOH

Skeletal structure

22. For the following molecules:

a. Add partial charges ( and ) to polar covalent bonds

b. Label the most electrophilic site(s) in each with E+; label the most nucleophilic site(s) with N:

23. For the following molecules: 1. Draw correct Lewis structures with all lone pairs illustrated; 2. Assign formal charges as necessary; 3. Draw at least one contributing resonance structure for each a. nitromethane, CH3NO2 b. methylnitrite, CH3ONO

24. Fill in any missing lone pairs in each ion. Draw all contributing resonance structures for each: a.

b.

25. What are the products for the following acid-base reaction?

What is the pKA of the alcohol on the right side of the equation? ________ What is the pKA of acetylene ion on the left side of the equation? ________ Which side of the equation does the equilibrium lie? __________ 26. What are the products for the following acid-base reaction? The pKA for an ammonium ion (NH4+) is 9 for reference.

What is the pKA of the conjugate acid of the benzoate ion on the left side of the equation? ________ Which side of the equation does the equilibrium lie? __________ 27. Which is the stronger acid, propylamine or propanamide? Briefly describe why (use of equations is strongly advised to support your argument!)

28. a. Provide the products of the following reaction (Draw in all lone pairs and formal charges!) b. Use curved arrows formalism to show electron movement c. Label and classify the acid and base (as Lewis or Bronstead) d. Label the nucleophile and electrophile

29. Below is a line drawing of BeCl2 a. Draw in all lone pairs; b. label atoms with appropriate hybridization; c. what is bond angle in BeCl 2? d. Draw an orbital picture of BeCl2 (label orbitals); e. would you expect BeCl 2 to be nucleophilic or electrophilic (explain in a sentence or two) ClBeCl

SCORE ____________/100