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Unformatted text preview: NAME: CHEMISTRY 1303 2‘ g 4- 5 1- 10 23 Examl 3. [5+ 2+ 3+§+§ 30
February 4, 2000 2 O 2 O [00 1. For the alkyne below: 1. BH3 +2 1. n-BuLi
2. H00‘ "X" “Y” caﬁHg "z" 2. EtBr
NaOH 3 3. Na/lq NH3 (a) Predict the major product for each reaction sequence (put answers in the boxes). (b) Give an (arrow pushing) mechanism for steps 1. and 2. (only) in sequence “Z”. (c) For step 3. in sequence “Z”, one of the intermediates is a ‘radical anion’. Draw a 3D
orbital picture of this intermediate. (b) mechanism: (c) 3D orbital picture: 2. When 3—butyn-l—ol is treated with 1 equivalent of sodamide, followed by methyl iodide, the
desired product 3—pentyn—1—ol is NOT formed to any significant degree. sodamide X 3—butyn— 1 —ol 2, Mel 3—pentyn-l—ol (a) Give the structures for the starting material and desired product, as well as for sodamide (in the
boxes above). (b) Given that a reaction other than the desired one above does indeed occur, predict the actual
product to this reaction (put answer in the box below). l. sodamide
3-butyn- 1 -ol 2. Mel (c) Explain brieﬂy why the desired reaction fails, and why the alternative reaction takes place. 3. On the chart below: HOCH3
A 3 P?” g ? 5 ~l~ 3 z I o
(a) Sketch the 'H NMR spectrum for compound A and assign all peaks (label ‘a’, ‘b’, etc.).
(b) Draw the relative integration for each signal.
(c) What is the multiplicity for the signal due to the methine proton in A?
(d) How many magnetically distinct carbon atoms are present in A? (e) Which carbon atom in A is likely to appear furthest downfield in its 13C NMR spectrum, and
what will its multiplicity be if it is not proton—decoupled? 4. Starting with l—hexene below and using any reagents, propose a short synthesis of Z—2—heptene
(hint: recall the main topic of discussion thus far!). Show work for partial credit. 6 7 H CH3 ...
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This note was uploaded on 02/01/2011 for the course CHEM 109B taught by Professor Aue during the Winter '08 term at UCSB.
- Winter '08
- Organic chemistry