2. Complete the following: Stereochemistry and regiochemistry may be important. type a) NaOH (aq) b) neutralize ➤ OMe a) LiAlH4, ether NMe2 f) b) H3O+ type b) a) HS SH ZnCl2, H+ b) Raney Ni g) type formation of thioacetal/desulfurization HO type Hell-Volhard-Zelinsky Reaction h) CO₂Et type Wittig Reaction H H₂N OEt OH DCC, CH2Cl2 Ph type a) NaH, THF CO₂Et d) b) BnBr, THE CO₂Et c) NaOH(aq); HCl(aq); heat type type HO type (COCI)2, cat DMF CH2Cl2 j) CI type a) NHEN b) LiAlH, THE c) H3O+ CO₂Me CO₂Me
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- II) Reactions - Complete the following reactions by drawing clear structures for the major organic product, reagent, or reactant. Remember stereochemistry (where applicable)! a) b) d) Notes on inputting answers in boxes: If the answer is a single compound, give its structure clearly. If the answer is a racemic mixture, you may give one enantiomer's structure clearly and write "racemic" or (+) under the answer. If the answer is a mixture of diastereomers, you must clearly give the individual structure of each product. . 1. NaH 2. Na, NH3 structure 1) F3C OOH 2) FeCl3, (1 equiv) H₂N. xs H₂, Pd/C 1) (sia)₂BH 2) H₂O2, NaOH H₂O 1. Cy₂BH 2. H₂O2, NaOH, H₂O FeCl3 (1 equiv)3) Draw the structures of the major organic product(s) for the following reactions. HI in CH₂Cl₂ 3 excess Cl₂ in H₂O H₂SO4 in H₂O (Two products) Br-Cl in THF 1) BH3 2) alkaline H₂O₂ OSO4 + HOOH2) Complete the following: Stereochemistry and regiochemistry may be important. a) b) C) d) e) type type type OCH 3 type type OH CH₂OH EAS - Nitration H₂ Lindlar Catalyst KMnO4 NaOH/H₂O + OCH3 "OCH 3 Br CHO OH OH f) g) h) i) j) type type OCH3 type type type OH Bronsted-Lowry acid base chemistry CO₂Me OH K Friedel-Crafts Acylation NO₂ a) LIAIH,₁, ether b) H₂O* H₂SO4 OH OH NH₂
- ces to access important values if needed for this question. Complete the equation for the following reaction by drawing a structural formula for the missing organic product. CH3CH2NH2 H20 CH,CH,C-OH • You do not have to consider stereochemistry. • You do not have to explicitly draw H atoms. • Draw cations and anions in separate sketchers. P. opy aste C. [F Visited CH4 M) M) M) ChemDoodle Submit Answer Retry Entire Group 5 more group attempts remaining1) 1544565- NH₂ 2) CI of & 7) 8) reagents used: FeCl3/Cl₂ HNO3/H₂SO4 MeCI/AICI3 ACCI/Et₂N SO3/H₂SO4 Pd/C, H₂ NaOH H₂SO4/heat ACCI= CI [Choose ]a) b) d) Complete each of these following reactions (i.e. fill in the boxes with the missing reagent(s) or major product(s). Indicate the stereochemistry if applicable. D Br 1- 2- NH 1- Br₂ (excess), KOH 2- H3O* Ph Br- H* 3- H¹, H₂O 1-SOCI₂, DCM 2- AICI 3 NaOEt EtOH 1. PhMgBr (excess) 2. H3O* NH 1- DCC 2- NH₂ 1-03, CH₂Cl2, -78 °C 2-(CH3)2S C9H1402
- Fill in the missing reactant, reagent and products. Indicate stereochemistry if necessary. Unless otherwise specified, assume the reagents are in excess.Acyl transfer (nucleophilic substitution at carbonyl) reactions proceed in two stages via a "tetrahedral intermediate." Draw the tetrahedral intermediate as it is first formed in the following reaction. H3C HCI / H2O `NH2 reflux • You do not have to consider stereochemistry. • Include all valence lone pairs in your answer. • Do not include counter-ions, e.g., Na", I, in your answer. • In cases where there is more than one answer, just draw one. opy aste Previous NextМЕСНANISMS 1,2-epoxy-1-methylcyclopentane undergoes both acid-catalyzed and base-catalyzed opening of the epoxide ring to form two different products. > Using ethanol as the solvent and an appropriate acid, show the steps in the acid catalyzed mechanism, writing structures for all products of the steps. Circle the major product(s). > Using ethanol as the solvent and an appropriate base, show the steps in the base- catalyzed mechanism, writing structures for all products of the steps. Circle the major product(s). 1,2-epoxy-1-methylcyclopentane CH3
- 5) Draw the structure, showing the stereochemistry, of the cyclic products 19 and 20, and the acyclic products 21 and 22. What is the relationship between 19 and 20? What is the relationship between 21 and 22? H3C. \CH2CH3 ...|l LIAIHA CH3ONA Br 19 + 20 21 22 + 19 20 21 22 relationship between 19 and 20 relationship between 21 and 22Draw a structural formula for the product of the reaction shown. CH3 CH3 **** + NC H CO₂CH3 H Use the wedge/hash bond tools to indicate stereochemistry where it exists. Show stereochemistry in a meso compound. • In cases where there is more than one answer, just draw one. - #[ ] در ChemDoodleⓇ наDraw the structure of the major organic product of the reaction below. CH(CH3)2 CHCI3 CH2CH3 • Use the wedge/hash bond tools to indicate stereochemistry where it exists. • Show stereochemistry in a meso compound. • If the reaction produces a racemic mixture, just draw one stereoisomer. C P ChemDoodle Cengage Learning | Cengage Technical Support