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practice exam 1 questions_key

practice exam 1 questions_key - Chemistry 1123:Practice...

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Unformatted text preview: Chemistry 1123:Practice Problems for Midterm 1, Thursday Feb 26, 2009 Question 1 (a) Propose reagents and reaction conditions for the following transformation, and a name for the functional group in the product. (5 points) HAHN/{L NH O N’ 2 New _ d n . 012* ’5’ GED/l Lama—L WW" / H / H ———> 0.:- Pl 03:5}: 13:0 1‘0 Ph Ph (b) Prepose reagents for the following transformation and a name for this type of reaction. (5 points) (c) Propose reagents for the following transformation and a name for this type of reaction. (5 points) Question 2 (a) Predict 2 possible products of the following reaction (6 points). O—COCI OMe AICI3, CHZCIZ (b) Provide a name for this type of reacfion:_EU_££££/£:[email protected]fi\o fl (4” ffiktflu (0) Provide a mechanism for the formation of one of the products from Part (a). (View; F; §M® (afl‘fifitl Q3 OJ {Ea—fig J I ”:3- O“??? +CR$Q693 1" 75:! l 5‘:wa Question 3 :8 4" (a) Provide a synthesis 0f\A_ from‘li. (Hint: the sequence involves a diazotization reaction) (25 points) Multiple 5' NH2 Steps CN _‘_’ ‘ Br Br B (b) The amino group is normally an ortho/para director. However, in the following nitration reaction, a significant amount of meta product (B) is formed, why? (10 points) NH2 NH 2 HNo3 ””2 _._.——’- H2804 N02 51 % 47% W MW brawn— Fxfifl Wrrfk aLVrwaW Question 4 (a) Provide a mechanism and transition states that rationalize the stereochemical outcome in the formation of A and B (10 points each). Label the transition states endo or em. 0 H o a H 0 < H 7|)L Diels-Alder ---“I{ E H H \ _—_—> (1)) Which is the major product (A or B)? (5 points) 1% WW iad’fiamflzo ywdmk we a): ij (ENDB Kari) Question 5 Explain with appropriate figures why the following resonance structures are not possible Question 6 (a) Provide mechanisms to explain the formation of A, B and C from D. (25 points) 0‘" / 3' NaNH2 in NHS / NHz / 0“ —————> / Heat / / NHz Me D Me A Me B c Me (b) Give two reasons why an SNZ reaction is unlikely to explain the formation of A in part (a). (8 points). NM /_ I A . 7‘ \R (Q— In Question 7 (From London; Problem 16.36) (a) The NMR spectrum of the sodium salt of cyclopentadiene (A) consists of a singlet, why? (10 points) (b) The methyl group in the following compound ( ) has an unusual chemical shift of 6 (-1.67), about 4 ppm lower than the chemical shift of a typical allylic methyl group, why? (10 points). ...
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