2444-110411

2444-110411 - QUIZ 7 Avg. 16.1 / 25 Stnd. Dev. 7.0 Exam 3....

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QUIZ 7 Avg. 16.1 / 25 Stnd. Dev. 7.0 Exam 3. Wed. Nov. 9 , 7:30 - 9:30 pm. No class on Nov. 9 - Q/A session
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Reactions 2 OH CO 2 Me CO 2 H CO 2 H O 1. SOCl 2 2. H 3 O + , heat 1. aq. NaOH 2. aq. H + 1. SOCl 2 2. EtOH 1. Hg(OAc) 2 , H 2 O 2. NaBH 4 2. butanoyl chloride DCC , 2-propanol cat. H + OH O CO 2 H CO 2 Et O O O O
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Reactions 3 OH CO 2 H CO 2 H O 1. SOCl 2 2. diethylamine 1. excess EtOH , cat. H + 2. excess CH 3 MgMr , THF 3. aq. H + 1. oxalyl chloride 2. Et 2 CuLi CH 3 NH 2 CO 2 H 25°C O O H 3 NCH 3 O NEt 2 OH O
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Reactions 4 CO 2 H Br 1. NH 3 , 25°C 2. 225°C 3. P 2 O 5 , heat 1. NaCN , THF O 2. 6N aq. HCl Br 1. NaCN , THF 2. CH 3 MgBr , THF 3. aq. H 3 O + , heat CH 3 CO 3 H CO 2 H CN O O + CH 3 CO 2 H O
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Disconnections 5 R OH R 1 R 1 R 1 O R 1 R O R 1 R 1 O R 1 R 1 O OH CO 2 R 1 O X R 1 O X R—CN R 1 O OH + R 1 —Mg (or Li) + + R 1 —Mg (or Li) + R 1 —Li + R 1 —Mg (or Li) (R 1 ) 2 Cd
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Spectroscopy RCOOH RCN IR: 1760-1710 cm –1 for C=O 2500-3300 cm –1 OH IR: saturated. 2250 cm –1 conjugated. 2230 cm –1 NMR: COO H 12-15 ppm CH -C=O 2.2-2.7 ppm NMR: C H -CN 2.3-3.0 ppm
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Spectroscopy IR: acid chloride C=O, 1810 (PhCOCl , 1770) anhydride 1820 + 1760 ester 1770 amide 1690 + 1650 NMR: a C=O 2.1 - 2.6 CO 2 H >12 (exchange with D 2 O) NH 2 1-6 (slow exchange with D 2 O) O=C-OCH 3.5-4.0
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Acid chloride , 1806 Acid anhydride , 1832 , 1761 Methyl acetate , 1748 acetamide , 1681 acetamide , 1655 + 1653 1700 Methyl acrylate , 1732 IR
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Chapter 21: Aromatic Compounds And Benzene Derivatives 9 • Benzene is a special hydrocarbon, There are hydrocarbons related to benzene that have two, three, or more rings fused together (polycyclic compounds). • The unifying concept of all these molecules is that they are aromatic, which means that they are especially stable with respect to their bonding and their structure.
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To begin, you should know: 10 The concept of resonance and resonance stability. (chapter 5, section 5.9.C) Identify the structure of benzene. (chapter 5, section 5.10) Nomenclature and structure of alkenes, alkyl halides, alcohols, amines, aldehydes and ketones. (chapter 5, sections 5.1, 5.6, 5.9) • Nomenclature and structure of carboxylic acids. (chapter 5, section 5.9.C and chapter 16, section 16) • Nomenclature and structure of carboxylic acid derivatives. (chapter 16, section 16.7 and chapter 20, section 20.1, 20.3-20.6) • The structure and nature of a ! -bond. (chapter 5, section 5.1.A) • The fundamental reactivity of alkenes. (chapter 6, section 6.4.E and chapter 10, section 10.1) • The formation, stability and reactivity of carbocations. (chapter 7, section 7.4.A and chapter 10, section 10.2) E2 elimination reactions of alkyl halides. (chapter 12, sections 12.1, 12.3) E1 elimination reactions. (chapter 12, section 12.4) • Be able to draw resonance contributors. (chapter 5, section 5.9.C and chapter 16, section 16.3) • The CIP rules for prioritizing substituents, groups and atoms. (chapter 9, section
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2444-110411 - QUIZ 7 Avg. 16.1 / 25 Stnd. Dev. 7.0 Exam 3....

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