7/30/2019 CHEM 210 Sample Exam 1 2010.doc

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

Condensed structure CH3CCCH2OH 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 chargesas necessary; 3. Draw at least one contributing resonance structure for eacha. 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.

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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 advisedto 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 movementc. Label and classify the acid and base (as Lewis or Bronstead)d. Label the nucleophile and electrophile

29. Below is a line drawing of BeCl2a. Draw in all lone pairs; b. label atoms with appropriate hybridization; c. what is bond angle in BeCl 2? d. Draw anorbital picture of BeCl2 (label orbitals); e. would you expect BeCl2 to be nucleophilic or electrophilic (explain in asentence or two)

ClBeCl

SCORE ____________/100