Ch 16 17 18 Problems - 1 Ch 16 Extra problems 1 Show the...

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1 Ch. 16 Extra problems 1. Show the major product (or products if more than one is formed in significant amount. Show stereochemistry if it is important. a. 1. NaBH4, EtOH 2. H + ,H 2 O(neutralize) O H CO 2 CH 3 b. 1. Excess PrMgBr 2) neutralize (H + ) + 1. BuLi 2. O Cl c. d. e. H 3 C P(C 6 H 5 ) 3 OCH 3 1. PhNHNH 2 , HCl O SH SH CH 3 O O Br - H + 2. neutralize
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2 2. Show the major product (or products if more than one is formed in significant amount. Show stereochemistry if it is important. 1. Ph 3 P 2. BuLi 3) O H OCH 3 O a. Br b. NaCN, H + , H 2 O c. NaCN, H + (less than 1 eq.) O d. H + , H 2 O e. H + (catalytic) O OH O CH 3 HO OH CH 3 O (HCN is not a reactive nucleophile, so a whole equivalent of acid removes the NC - ) PhNHNH 2
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3 3. Show reagents and intermediate compounds that would be isolated for the following conversions. Reagents stable enough to buy may be used. Do not give mechanisms. a. O H OCH 3 O O H OH b. c. OH O d. O H NOH O H O O
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4 4. a. N HO H H H + Cl - + O O O H 2 O C N HO H H + 3 H 2 O + 3 HCl 3 A B C C is the _____________________ of carbonyl compound ________________( D ) (name of class of compound) (name of D ). b. Give an arrow-pushing mechanism, using A as an acid, which converts B to 3 D. c. Give an arrow-pushing mechanism which converts A + D to C + HCl using H 2 O as a base (structure of D should be in your answer to part a). b. Write the structure and give an example of using: DIBAL-H Ozone (Lewis structure including lone pairs
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5 5. a. O O O H 2 O Briefly: how did you know which type of C=O to hydrate? b. Give the structure of a ketone which will not form a cyanohydrin upon treatment with cyanide and acid c. Put in order. Fins a 2,4-DNP derivative fastest: 1=fastest, 4=slowest H H 3 C O O H O H Cl 3 C O d. Draw the structure(s) of the oxime(s) from acetaldehyde (empirical formula C 2 H 5 NO). Write the multiplicity expected for each type
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Ch 16 17 18 Problems - 1 Ch 16 Extra problems 1 Show the...

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