replace_key - ANSWERS for Practice Problems in Synthesis...

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Unformatted text preview: ANSWERS for Practice Problems in Synthesis Using the Reactions of Alkenes, Alkynes, Alkyl Halides, Alcohols, Aldehydes, Ketones, Ethers and Epoxides SOCI M a. CH3CH20H —+> CH3CH2CI “ia- CH3CH2MgCI (3H Pyrldme ether CHCHZCH3 OH H I. combine 1 + 2.H :‘H o E POC13 1- 03 C\ 2 CHCH CH ridine \O I 2 3 W 2. Zn / CH3COOH ,0 CH C\ H SOCl M b. CH3CH20H -—~.—.3—> CH3CH2C1 —g—> CH3CH2MgCl HO CHZCH3 pyrldme ether 1. combine 0H 0 >2lH+,HZO’ 7H3P04/A 00 /H so —3——£_i> CHZCH3 HZO/acetone (RH [CHZCH3 CHCHZCH3 C\ NaBH4 / H20 \0 1- 03 4-—-—--— alcohol 1,0 2. Zn/ CH3COOH CHZOH C\ H OH Br MgBr ether ether - l. combme (a + POCI3 6 ©/ 6 pyridine CHZC]2 (3 CH 0 C33 1_Hg(OCCH3)2/H20 Rm ‘3“ CrO3/H2804 \ 3 n d. /CH—CH:CH2 /CH—CH—CH3 m—h- /CH-C—CH3 CH3 2. NaBH4 CH3 2 ace one CH3 1.BH3-THF 2. H202 CH CH CH \ 3 SOCI2 \ 3 Mg \ 3 CH-CHz-CHg-OH “T—e’ CH—CHz—CHZ-m —n—> CH-CHz-CHZ-MgCI / pyrldme / ether / CH3 CH3 CH3 C\I._I3 /CH3 /CH—CH2—CH2—C—CH CH3 CH3 CH3 ANSWERS for Practice Problems in Synthesis Using the Reactions of Alkenes, Alkynes, Alkyl Halides, Alcohols, Aldehydes, Ketones, Ethers and Epoxides (continued) 6 C\H3 _ l.BH3-THF C\H3 SOC12 C\H3 ' ,CH"CH—CH2 w——> CH-CHfCHz-OH .—.> CH—CHZ—CH2-C1 CH 2. HZOZ/NaOH / pyridine / 3 CH3 CH3 f] Ph3P N9 CI‘O3CI- C" | \ 3 ® H [FCC] CH-CHz-CHz-PPhg, (11-1202 CE C\H3 {/0 CH3 CH3 xCH—CHZ’Q C\H3 \ / fCH-CHg-CHzCH-CHz—CEI CH H /CH—CH2-CH:Pph3 CH3 CH3 CH3 f :1?“ . —> ,CH CHzCH2q\ 3 2. Zn/CH3COOH CH2 LFe/HCI 2. Na+ OH" topH 12 N CH NH alcohol ,CH3 cnzcnzc“ 0 9 ‘?H W g_ (RH H_CE 9—C=N1)LiA1H4/ether (EHCHZ-NHZ fiH—+ K CEN(cat.) H 2)H20/sto4 H 3)Na0H —- pH 12 O C\ H (PH 0/ H \ CZNWCH2_CH G pH 5, alcohol ANSWERS for Practice Problems in Synthesis Using the Reactions of Alkenes, Alkynes, Alkyl Halides, Alcohols, Aldehydes, Ketones, Ethers, and Epoxides (continued) PCC H rh—CHZCIz CH3—0H h m mew mm 1—H) 0% Wm“ e r 2)H /H20 CH3 PBI‘3 :CH—CHz—OH % ether CH3 (:53 /0 ,CH3 /CH-C\/ CH=CH—C\H CH3 H CH=PPh3 1)Ph3P/A/benzene CHzBr CH3 A 2) butyllithium / ether < 9 > 1 OH 1) Hg O—C—CF3 2 )Hg(0Ac)2 / H20 CH3CH2-CH=CH2 I _ CH3CH2—CH2CH2 CH3CH2—CH—CH3 1. 2)NeBH4 / H20 2)NaBH4 /H20 1 CH3CH2—(IZH—O—CIIH—CH2CH3 CH3 CH3 1) / (PH /0 . BH THF J- CH3CH2-CH2CH2 3 CH3CH2—CH2—CH2 PCC CH3CH2_CH2_C/ 2) H202 INaOI—I / H20 CH2012 \H 1)o Ilgr 5’19?“ 3 HBF __ _ Mg _ _ 2) Zn/CH3COOH ether CH3CH2 CH CH3 ether CH3CH2 CH CH3 00 1)combine [H2CZO] + CH3CH2'C CH \H I 3 2)H+/H20 NaBHétl/ H20 CH3CH2-CH—(I3H—CH2CH2CH3 21100 01 _ 1)Na+ H: 0H CH3 CH3CH2—CH2—OH P I 12 I 2) l‘CHgCH2CH3 CH3CH2—CH—ClH—CH2CH2CH3 O (51-12%ch3 ANSWERS for Practice Problems in Synthesis Using the Reactions of Alkenes, Alkynes, Alkyl Halides, Alcohols, Aldehydes, Ketones, Ethers, and Epoxides (continued) ‘3 (I? k. ,C\ SOC! ,C\ HOCH CH OH O 0 CH3 CH2CH2-OH -d-2 CH3 CHQCHz-Cl 2 2 >< Pm me H2804/A CH CH _Cl H20 removal CH3 2 2 CH3 I f \ M / th CH3—Si-Cl 0 0 Oi g 6 er I CH3 H CH3 .‘ /C\ >< CH3 -Sl-—O-CH2CH2 CH3 CH3 CHZCHz—MgCl [CHaCHflsN= (EH 3 1) combine / \ 2)H+/H20 O 0 O O OH _ BuélN+F >< OH CH3 | | CH3 CH2CH2—IC—CH2CH2—OH CH3 CH2(1H2-c:—CH2CH2--o—:Si—CH3 HF l CH3 CH3 CH3 0 H2804 H20 OH H walm , \ | Na2Cr207/H2804 /c\ 9H ,9 CH3 CH2CH2‘C—CH2CH2_OH CH3 CHZCH2_C_CH2_C | HzO/acetone | \ CH3 CH3 OH 0 Br M 1' / - 1 Eu Mg gB 1) €1le_\CH2 CHZCHZ OH . ——.' —-—> O m >< H20 / acetone /, CH2C Na CrO /H so 0’ \OH 2 27 2 4] (I? 0 (:1 C \ _ \ CH2 (If 0 0H G/CHg CH2C12 “Es/m 0H Q combine+ 0L 2) H202 / H2O Na H' (cat) Gem-0H ...
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This note was uploaded on 04/02/2008 for the course CHEM 301 taught by Professor Morrow during the Spring '08 term at New Mexico.

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replace_key - ANSWERS for Practice Problems in Synthesis...

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