Assign_ intro-6 - CH 3 CH 2 CH 2 H CH 2 C CH 3 CH 2 H CH 3...

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Assignment Intro-6 1. Rank the following compounds in order of increasing acidity: (when more than one type of H is present in a molecule, the most acidic H is underlined) A. NH 3 , H 2 O, HF E. CH 3 CH 2 CH 3 , Cl-CH 2 CH 2 -OH , CH 3 CH 2 -OH B. HCl, HBr, HI F. H -C C-CH 2 -CH 3 CH 3 CH 2 CH 2 CH 3 H 2 C CH-CH 3 , , C. NH 3 , H 2 O, H 2 S G. HCl, H 2 O, H 2 S D. CH 3 OH, CH 3 NH 2 , CH 3 CH 3 2. Rank the following compounds in order of increasing base strength (Hint: there are two ways to work this: (1) convert each base to its conjugate acid, then rank the acids in order of their strength. .. the order of the base strength of their conjugate bases will be the reverse of the order of their acid strength, OR. (2) In any series, the weakest base is the most stable anion (has less affinity for H + ), the strongest base is the least stable anion.) A CH 3 -CH 2 : CH 3 -O : .. .. CH 3 -N-H .. .. B. CH 3 .. HO .. .. : Br .. .. : : C. C C : CH 2 CH 2 : CH CH : 3. The pK a of three different C-H bonds is given below
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Unformatted text preview: CH 3 CH 2 CH 2 H CH 2 C CH 3 CH 2 H CH 3 C O CH 2 H pK a pK a pK a 50 43 19.2 = = = A. For each compound, draw the conjugate base, including all possible resonance structures. B. Explain the observed trend in pK a 4. The pK a of nitromethane (see below) is 10, making its C-H bond more acidic than most C-H bonds. Explain. CH 3-N O O : : .. .. : + nitromethane 5. For each pair below, select the stronger acid A. Br-CH 2 CH 2-OH vs CH 3-CH 2-OH B. H 2 S vs H 2 Te C. Br-CH 2-C O OH Br 2 CH-C O OH vs D. CH 3 C O CH 3 vs CH 3-CH 2-CH 3 6. The indicated hydrogen in 1,4-pentadiene is more acidic than the indicated hydrogen in pentane . Explain H H 1,4-pentadiene H H pentane 7. Which of the indicated protons in each molecule is more acidic ? Explain your choice. O H H A. B. O H O H O H O H O C....
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This note was uploaded on 04/07/2009 for the course CHE 311 taught by Professor Drake during the Fall '08 term at American International.

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Assign_ intro-6 - CH 3 CH 2 CH 2 H CH 2 C CH 3 CH 2 H CH 3...

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