Tutorial 4 - H 2 SO 4 , cold dilute (C) Br 2 H 2 O(l) (D) H...

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CHEMISTRY 1AA3 Feb. 1-5, 2010 TUTORIAL PROBLEM SET 4 __________________________________________________________________________ Page 1 of 3 1. Label the sp and sp 2 hybridized carbon atoms and any sp 3 hybridized heteroatoms in the following molecule. 2. Fill in the missing products for the following reactions. 3. How many degrees of unsaturation are present in each of the following molecules? (a) C 6 H 10 O (b) C 4 H 8 (c) C 5 H 12 O (d) C 5 H 9 Br 4 Arrange the following carbanions in the order of increasing stability: (i) (ii) (iii) (iv) - - - - (CH 3 ) 2 CCH(CH 3 ) 2 CH 3 CHCH(CH 3 ) 2 CH 3 CH 3 CH 2 CH 2 5. Propose a synthesis of cyclohexanol and chlorocyclohexane from cyclohexene. 6. For each of the following schemes, choose the reagents needed to complete the transformations shown:
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CHEMISTRY 1AA3 Feb. 1-5, 2010 TUTORIAL PROBLEM SET 4 __________________________________________________________________________ Page 2 of 3 (a) (i) (ii) (A) H 2 , Pd/C H 2 SO 4 , cold dilute (B) H 2 , Lindlar’s catalyst
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Unformatted text preview: H 2 SO 4 , cold dilute (C) Br 2 H 2 O(l) (D) H 2 , Lindlars catalyst H 2 SO 4 , hot, concentrated (E) HBr dilute NaOH, 25 C (b) (i) (ii) (A) dilute OH , 25 C H 2 (B) conc. OH , heat H 2 /Ni (C) H 2 O H 2 /Pt (D) conc. H 2 SO 4 , heat H 2 /Pd (E) dilute H 2 SO 4 , 25 C H 2 /Ni 7. Devise a scheme to accomplish the following transformations. (a) convert bromomethane to ethanoic (acetic) acid (b) convert cyclohexane to chlorocyclohexane 8. Stinker. The p K a of acetylene is 25 while that for ethylene is 44. Explain the difference based on the hybridization of the appropriate C-atoms. 9. Old exam question: Which of the following precursors could not be used in the synthesis of compound 1 ? CHEMISTRY 1AA3 Feb. 1-5, 2010 TUTORIAL PROBLEM SET 4 __________________________________________________________________________ Page 3 of 3 (A) i (B) ii (C) iii (D) iv (E) v...
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This note was uploaded on 04/13/2011 for the course CHEM 1AA3 taught by Professor H during the Spring '08 term at McMaster University.

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Tutorial 4 - H 2 SO 4 , cold dilute (C) Br 2 H 2 O(l) (D) H...

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