Unformatted text preview: ORGANIC CHEMISTRY CH231 OCTOBER 2004
FIRST EXAMINATION ' Lg‘) 1.Show , by illustration , how aluminum chloride can form a coordinate covalent bond . Note :
aluminum has three valence electrons . (171‘) 2. Draw all of the constitutional isomers for the cyclic compounds having the molecular formula C5H10
Us) 3. Write the conjugate acid of (a) 02H5NH2 (b) CH3O' (c) CH3OH (d)(OH -) .
, 4.Draw a potential energy diagram for the concerted reaction A + B = C .The reaction is exothermic . <
If) Label all parts of the diagram . — y) 5. From the rate equation . rate = (Ag‘) ( MeaCBr‘ ) , deduce a two step mechanism for the reaction
0 :7 MeacBr +Ag’ + CH3COO' = Me30000H3 +AgBr .Be sure to label the slow and fast _ step.
(/ 0) 6. The standard free energy change fbr the rotation of a 0-0 bond in ethane is about 3 Kcal / Mol at , 25 degrees C . Calculate the the percent distribution for the staggered / eclipsed conformers .
(l 1;”) 7. Provide lUPAC names for the following : (a) (b) O__<] (c)
' I CH3 (‘1) (e) C”3‘C(CH3)2'C”2C”C”3'C“3 CHacnzcnch-cHZCHZCHZCH3 H3CT—FCH3
(/5) 8. Write a structure for the following : _ (a) neopentyl alcohol (b) bicycle [ 3.1.1 ] heptane (c) 2-mehtyl-2—pentanol
[I 5’ ) 9. Starting with any two compounds containing. no more than four carbons . write a synthesis for
dodecane CH3(CH2)10)CH3 . (7 U) 10 Draw the most stable conformer Of 1-tert—butyl-4-methylcyclohexane . Note : R = 1.987 Cal / moi-Degree ...
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