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Practice_Quiz_12_blank - O C 6 H 5 CH 3 CHCH 2 CH 2 CHCH 2...

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Complete the reactions below by providing the missing products inside the boxes. Be careful to give all the important organic products, as requested. It is not necessary to give the byproducts of the reactions. Stereochemical details in the products must be indicated, wherever they are important. "Workup" means treatment with water and bringing the reaction mixture to neutral pH. (1) Chemistry 322aL Practice Quiz 12 (A) HCCH 2 CHCH 2 COCH 3 O = O CH 3 + NaBH 4 H 2 O, CH 3 OH (B) CH 2 OH CH 3 + N . CrO 3 . HCl (PCC) CH 2 Cl 2 C 8 H 8 O
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(C) CH 3 CH 2 CH 2 CH 2 Br (i) Mg/dry ether (ii) CH 3 CCH 3 O = (iii) workup C 7 H 16 O (D) CH 3 CHCH 2 CH 2 Br CH 3 (i) Mg/dry ether (ii) CH 2 CH 2 O (iii) workup (E) CH 3 CH 2 COCH 2 CH 3 O (i) excess CH 3 CH 2 MgBr/dry ether (ii) workup C 7 H 16 O
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CH 3 CH 2 COCH 3 O = CH 3 CH 2 COH CH 3 CH 3 (2) Answer the questions below. (A) What are the formal oxidation states of each carbon atom in the two following structures? (B) Which oxidizing or reducing agent is needed for each of the following chemical transformations? CO 2 CH 3 CH 2 CCH 3 O CH 2 OH CH 2 CHCH 3 OH CH 2 OH CH 2 OH CHO CHO CH 3 CCH 2 CH 2 CHCH 2 CO 2 C 2 H 5
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Unformatted text preview: O C 6 H 5 CH 3 CHCH 2 CH 2 CHCH 2 CO 2 C 2 H 5 C 6 H 5 OH (3) Complete the multi-step synthesis below by supplying the missing structures inside the boxes. (i) BH 3 .THF/THF (ii) H 2 O 2 , KOH, H 2 O PBr 3 Mg/ether CH 3 CH 2 CCH 3 O (i) (ii) workup C 10 H 20 O (4) Use retrosynthetic analysis to design two syntheses of 3-phenyl-3-pentanol using ethyl iodide and any needed carbonyl compounds as starting materials. CH 3 CH 2 CCH 2 CH 3 OH C 6 H 5 (5) Circle the stronger base in each pair below. KOH KOBu-t CH 3 C CNa NaNH 2 KOBu-t NaNH 2 CH 3 Li NaNH 2 CH 3 MgI KOH CH 3 MgI CH 3 C CNa (6) Circle the solvent(s) that is(are) incompatible with each of the indicated reagents below. reagent solvent list C 6 H 5 MgBr diethyl ether ethyl alcohol water THF LiAlH 4 NaBH 4 ethyl alcohol water THF diethyl ether ethyl alcohol water THF...
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Practice_Quiz_12_blank - O C 6 H 5 CH 3 CHCH 2 CH 2 CHCH 2...

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