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Organic Chemistry II Quiz 12: Acidity of Molecules, Enolates, and Reactions - Prof. Joseph, Quizzes of Organic Chemistry

A quiz from an organic chemistry ii course, covering topics up to section 19.3. The quiz includes questions on the acidity of molecules, drawing enolates from a given ketone, identifying major products of reactions, and drawing the structure of a diene from its ozonolysis products.

Typology: Quizzes

2009/2010

Uploaded on 02/25/2010

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CHM 2212-Organic Chemistry II Name________________________(1)
April 19, 2002
Quiz #12 (25 points)
(Covering material through section 19.3)
1. (4) Rank the following molecules in order of decreasing acidity: use '1' for
the most acidic, '2' for the next,...and '4' for the least acidic.
CH3CCH2CCH3
O O
CH3CH3CH3CCH3
O
CH3CCHCCH3
O O
NO2
2. (4) (a) Draw all possible enolates derived from the following ketone (there
are two of them). Remember that an enolate is formed by removing an a–H.
Draw each enolate in the resonance form with the negative charge on the
oxygen.
CH2CCH3
O
(b) Which enolate of the two do you consider to be more thermodynamically
stable? Why?
pf3

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CHM 2212-Organic Chemistry II Name________________________(1) April 19, 2002 Quiz #12 (25 points) (Covering material through section 19.3)

  1. (4) Rank the following molecules in order of decreasing acidity: use '1' for the most acidic, '2' for the next,...and '4' for the least acidic. CH 3 CCH 2 CCH 3

O O

CH 3 CH 3 CH 3 CCH 3

O

CH 3 CCHCCH 3

O O

NO 2

  1. (4) (a) Draw all possible enolates derived from the following ketone (there are two of them). Remember that an enolate is formed by removing an a–H. Draw each enolate in the resonance form with the negative charge on the oxygen. CH 2 CCH 3

O

(b) Which enolate of the two do you consider to be more thermodynamically stable? Why?

  1. (10) Provide the structures for AE below (if possible, comment on any relevant stereochemistry as well).

A B

E D

(CH 3 ) 3 CO–K+

tBuOH

D

C

  1. CH 3 CH 2 C–Cl

O

2) H 2 O

NH 2 NH 2 , HO–

D

Br 2 hn

  1. OsO 4
  2. NaHSO 3 , H 2 O , AlCl 3