Homework Answers
In the first step Grignard reagent is formed. As in the reactant the halide atom (Bromine) is more electronegative than carbon atom so bromine has negative charge and carbon atom has positive charge. After the reaction with magnesium, in the presence of ether (solvent), the magnesium atom comes between the carbon atom and bromine atom. And now the carbon atom becomes negatively charged because carbon is more electronegative than magnesium.
In the second step, the Grignard reagent attack on the epoxide. The carbon atom of Grignard reagent is negatively charged and it is nucleophilic (electron rich) in nature. In epoxide the oxygen is more electronegative so the Grignard reagent attacks on the carbon atom (electron deficient) adjacent to oxygen atom in epoxide.
In the third step, O- abstracts one of the proton from the H3O+
So the final answer is written below
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-00= dil H,O (d) HCECH NaHCH.CHEO ether in H,90 (H,180 has isotopically labelled O) 2 equiv...
give mechanism 3.1 sc)o 2. CH3(CH)&B \ 3. Нзо", heat O/ d) 1. NaOEt 2. dil....
give mechanism
3.1 sc)o 2. CH3(CH)&B \ 3. Нзо", heat O/ d) 1. NaOEt 2. dil. H3O OEt 1. LDA, -78°C 2. CH CH2Br f) 1. NaOH, 2 2. H30 1. NaOH, heat g) xs NH3 (SN2) 1. Br2, PBr3 2. H20 h)
H,Lindlar H -CCCH 1. BH 2.H,O KCN но CH &H,C o- dil. H,SO HCI 1. BH...
H,Lindlar H -CCCH 1. BH 2.H,O KCN но CH &H,C o- dil. H,SO HCI 1. BH C CCH Hyc 2. НаО2 Br KOH, Alc., Heat
For each reacuon ere s only as an aid for you. 1) KOH, H-O, heat Diethyl malonate B 1) Ph3P, ether 2) nBuLi, ether CIH1...
For each reacuon ere s only as an aid for you. 1) KOH, H-O, heat Diethyl malonate B 1) Ph3P, ether 2) nBuLi, ether CIH1204 2) H, H2O, heat C1SH2406 CHH1202 NaOEt, EtOH Br OCH2CH3 3) PHCHO NH/heat Note: The C-13 NMRS for Structures C, D, and E each show 7 resonances LIAIH D E C1HNO ether C1H1SN Br 1) SOCI2, pyridine F 2) CH3OH 1) CH2COCI,AICI3 1) Mg(s), Et20 H 2) diisopropyl amine, pH 4.5, NaBH3CN 2) CO2 (s)...
2. Predict the product. CH,CHINH Or . 1. excess CH 1 2. Ag,0,H,O heat 5. Match...
2. Predict the product. CH,CHINH Or . 1. excess CH 1 2. Ag,0,H,O heat 5. Match the reagents to the corresponding reaction. G. H20 H. xs CH3CH2NH2 A. SOCI2, pyridine B. Ethanol, pyridine C. 1) xs LAH 2) H20 D. 1) xs CH,CHMgBr 2) H30 E. 1) NaOH 2) H30* F. 1) DIBAH 2) H20 1. 1) LiAl(OR)2) H20 J. (CH2CH2) Culi K. xs NH3 L. 1) NaOH 2) CHÚCHỊCHÚCOCI M. Butanol, H
ta 2.0 L. O .O. HC-CC- 24 d. HC OH 1 2 CH,CHỊU. 2.H,0 c. CH...
ta 2.0 L. O .O. HC-CC- 24 d. HC OH 1 2 CH,CHỊU. 2.H,0 c. CH CH 1. SOCH OH 2. LIAHOT-Bus CH,CHE 1. SOCI OH 2 CH CHO Php C ake h. CH CH, NaBH CH,CH, OH 1. AH,THE 2 HOHO I CHOCHEM 1. CH CH CH.CH 3. SO.
20) 20) Which of the following syntheses gives 3-methyl-1-hexanol? O Mg 1) A) 2-bromopentane diethyl ether...
20) 20) Which of the following syntheses gives 3-methyl-1-hexanol? O Mg 1) A) 2-bromopentane diethyl ether 2) Mg B) 2-bromohexane - diethyl ether 1) HC=0 2) H C) 3-bromopentane Mg diethyl ether 1) CH2CH=0 2) H Mg D) 1-bromobutane diethyl ether 1) CH3CCH; 2) D)D А) А В) В c) C 21) Identify the reagent needed to carry out the following conversion. 21) 0 CHOH CHOH ?, CH CH B) PCC/CH2Cl2 D) K2Cr2O7, H2SO4/H20 A) Os04 C) HIO4
a.) H H_Cro acetone b.) 1. XS KMnO,/KOH/HOIA 2.H30* c.) ni XS NaBH,, H,0 H OH...
a.) H H_Cro acetone b.) 1. XS KMnO,/KOH/HOIA 2.H30* c.) ni XS NaBH,, H,0 H OH d.) o 1. XS LAIH/THF/-78 °C 2. H20 H OH e.) NaNH / lig NH3 f.) Br 1. Mg/THE 2. CO2 3. H30 9.) Ph Ph cyclopropene HF CH h.) OH 1. PCCICH.CH 2. Pri 3. N,Cag) 1. LITHF 2.CO 3. NH.Ca) HNO, NH 1. HNO () 2. NaSCH CH.CH AICI, 3-chloro-2-methylpentane m.) 1.Pr.CI. AICI 2. NBS, CCH n.) OH XS H.COM acetone OH...
Ph cyclopropene HF CH h) OH 1. POCICH.Ch 2. Pri 3 NH4Cl ag) 1.) 1. Li/THE...
Ph cyclopropene HF CH h) OH 1. POCICH.Ch 2. Pri 3 NH4Cl ag) 1.) 1. Li/THE 2.CO 3.NH.CH HNO k.) NH 1. HNO (aq) 2. NaSCH CH.CH AICI, 3-chloro-2-methylpentane m.) 1.Pr.CI. AICI 2. NBS, CCU. n) -OH XS H.CO acetone он 0.) OH XS Bobbit's SiO, CH.CH -OH 1. Ch. AICI 2 NaOH, 30 C 4,000 psi 3. HCI 9.) SCH 2Na, ETOH, NH, r.) 1. LIETO 2. oxirane 3. H,00 1.2 PY-MOBI OMe 2. NHCl(aq) t.) 1. Cl/ Feer...
2. Write out the required reagents/reaction conditions or Lewis structures for the productis) produced for 18...
2. Write out the required reagents/reaction conditions or Lewis structures for the productis) produced for 18 of the following 21 reactions. Answer only (18), otherwise only the first (18) will be graded (72 pts/4 pts each) NOTE: C(=O) represents C=0 a. CH3CH2OH → CH3-C(=O)-H b. CH3-C(=O)-CI CH3-C(=O)-CH3 C. CH3-CEC-H CH3CH2-C(=O)-H d. CH3-C(EO)-H H-CEN e. CH3-C(=O)-H (CH3)2-CH-OH f. CH3-C(=O)-CH3 + (CH3)2NH / H30 9. CH3-C(=O)-CH3 + CH3OH (2 equiv) / H30* → h. C6H5-CH3 C6H5-CO2H I. CH3-Mg-CI CH3-CO2H 1 CH3-CO2H CH3CH2-OH...
(2) NaBH4 (2) H202 OH cold, dilute KMnO4 "ОН H,C H,C HCO,H H,O с-с CH CH2CH,...
(2) NaBH4 (2) H202 OH cold, dilute KMnO4 "ОН H,C H,C HCO,H H,O с-с CH CH2CH, CH,CH2CH Predict the major products of the following reactions, including stereochemistry where appropriate. (a) (R)-2-butanol + TsCl in pyridine c) cyclooctanol + CrO3/H2SO4 (e) cyclopentylmethanol + Na2Cr 01/H2SO4 (g) n-butanol + HBr (i) potassium t-butoxide + methyl iodide (k) cyclopentanol + H2SO4/heat (m) sodium ethoxide +1-bromobutane (b) (S)-2-butyl tosylate +NaBr (d) cyclopentylmethanol + CrOs pyridine HC cyclopentanol + HCI/ZnCl2 (h) cyclooctylmethanol + CH3CH2MgBr (G)...
give mechanism
3.1 sc)o 2. CH3(CH)&B \ 3. Нзо", heat O/ d) 1. NaOEt 2. dil. H3O OEt 1. LDA, -78°C 2. CH CH2Br f) 1. NaOH, 2 2. H30 1. NaOH, heat g) xs NH3 (SN2) 1. Br2, PBr3 2. H20 h)
H,Lindlar H -CCCH 1. BH 2.H,O KCN но CH &H,C o- dil. H,SO HCI 1. BH C CCH Hyc 2. НаО2 Br KOH, Alc., Heat
For each reacuon ere s only as an aid for you. 1) KOH, H-O, heat Diethyl malonate B 1) Ph3P, ether 2) nBuLi, ether CIH1204 2) H, H2O, heat C1SH2406 CHH1202 NaOEt, EtOH Br OCH2CH3 3) PHCHO NH/heat Note: The C-13 NMRS for Structures C, D, and E each show 7 resonances LIAIH D E C1HNO ether C1H1SN Br 1) SOCI2, pyridine F 2) CH3OH 1) CH2COCI,AICI3 1) Mg(s), Et20 H 2) diisopropyl amine, pH 4.5, NaBH3CN 2) CO2 (s)...
2. Predict the product. CH,CHINH Or . 1. excess CH 1 2. Ag,0,H,O heat 5. Match the reagents to the corresponding reaction. G. H20 H. xs CH3CH2NH2 A. SOCI2, pyridine B. Ethanol, pyridine C. 1) xs LAH 2) H20 D. 1) xs CH,CHMgBr 2) H30 E. 1) NaOH 2) H30* F. 1) DIBAH 2) H20 1. 1) LiAl(OR)2) H20 J. (CH2CH2) Culi K. xs NH3 L. 1) NaOH 2) CHÚCHỊCHÚCOCI M. Butanol, H
ta 2.0 L. O .O. HC-CC- 24 d. HC OH 1 2 CH,CHỊU. 2.H,0 c. CH CH 1. SOCH OH 2. LIAHOT-Bus CH,CHE 1. SOCI OH 2 CH CHO Php C ake h. CH CH, NaBH CH,CH, OH 1. AH,THE 2 HOHO I CHOCHEM 1. CH CH CH.CH 3. SO.
20) 20) Which of the following syntheses gives 3-methyl-1-hexanol? O Mg 1) A) 2-bromopentane diethyl ether 2) Mg B) 2-bromohexane - diethyl ether 1) HC=0 2) H C) 3-bromopentane Mg diethyl ether 1) CH2CH=0 2) H Mg D) 1-bromobutane diethyl ether 1) CH3CCH; 2) D)D А) А В) В c) C 21) Identify the reagent needed to carry out the following conversion. 21) 0 CHOH CHOH ?, CH CH B) PCC/CH2Cl2 D) K2Cr2O7, H2SO4/H20 A) Os04 C) HIO4
a.) H H_Cro acetone b.) 1. XS KMnO,/KOH/HOIA 2.H30* c.) ni XS NaBH,, H,0 H OH d.) o 1. XS LAIH/THF/-78 °C 2. H20 H OH e.) NaNH / lig NH3 f.) Br 1. Mg/THE 2. CO2 3. H30 9.) Ph Ph cyclopropene HF CH h.) OH 1. PCCICH.CH 2. Pri 3. N,Cag) 1. LITHF 2.CO 3. NH.Ca) HNO, NH 1. HNO () 2. NaSCH CH.CH AICI, 3-chloro-2-methylpentane m.) 1.Pr.CI. AICI 2. NBS, CCH n.) OH XS H.COM acetone OH...
Ph cyclopropene HF CH h) OH 1. POCICH.Ch 2. Pri 3 NH4Cl ag) 1.) 1. Li/THE 2.CO 3.NH.CH HNO k.) NH 1. HNO (aq) 2. NaSCH CH.CH AICI, 3-chloro-2-methylpentane m.) 1.Pr.CI. AICI 2. NBS, CCU. n) -OH XS H.CO acetone он 0.) OH XS Bobbit's SiO, CH.CH -OH 1. Ch. AICI 2 NaOH, 30 C 4,000 psi 3. HCI 9.) SCH 2Na, ETOH, NH, r.) 1. LIETO 2. oxirane 3. H,00 1.2 PY-MOBI OMe 2. NHCl(aq) t.) 1. Cl/ Feer...
2. Write out the required reagents/reaction conditions or Lewis structures for the productis) produced for 18 of the following 21 reactions. Answer only (18), otherwise only the first (18) will be graded (72 pts/4 pts each) NOTE: C(=O) represents C=0 a. CH3CH2OH → CH3-C(=O)-H b. CH3-C(=O)-CI CH3-C(=O)-CH3 C. CH3-CEC-H CH3CH2-C(=O)-H d. CH3-C(EO)-H H-CEN e. CH3-C(=O)-H (CH3)2-CH-OH f. CH3-C(=O)-CH3 + (CH3)2NH / H30 9. CH3-C(=O)-CH3 + CH3OH (2 equiv) / H30* → h. C6H5-CH3 C6H5-CO2H I. CH3-Mg-CI CH3-CO2H 1 CH3-CO2H CH3CH2-OH...
(2) NaBH4 (2) H202 OH cold, dilute KMnO4 "ОН H,C H,C HCO,H H,O с-с CH CH2CH, CH,CH2CH Predict the major products of the following reactions, including stereochemistry where appropriate. (a) (R)-2-butanol + TsCl in pyridine c) cyclooctanol + CrO3/H2SO4 (e) cyclopentylmethanol + Na2Cr 01/H2SO4 (g) n-butanol + HBr (i) potassium t-butoxide + methyl iodide (k) cyclopentanol + H2SO4/heat (m) sodium ethoxide +1-bromobutane (b) (S)-2-butyl tosylate +NaBr (d) cyclopentylmethanol + CrOs pyridine HC cyclopentanol + HCI/ZnCl2 (h) cyclooctylmethanol + CH3CH2MgBr (G)...
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