310-4 - CH 310 N T Th 2-3:30 LECTURE 4 Textbook Assignment...

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CH 310 N T Th 2-3:30 LECTURE 4 Textbook Assignment: Chapter 12 cont’d Homework (for credit): POW 2 posted- POW 1-Due today Today’s Topics: NMR-theory-integration & splitting Notice & Announcements: TA office hrs: Kyle Williams Wed: 3-4 WEL 4.308 Jing Li Fri: 9-10 BME 6.102 Luz Carrillo Mon: 2-3 Cubicle “A” Organic Lecture Series 2 • Equivalent hydrogens: Equivalent hydrogens: have the same chemical environment – a molecule with 1 set of equivalent hydrogens gives 1 NMR signal H 3 C CC CH 3 H 3 C 3 3 CCH 3 ClCH 2 2 Cl Propanone (Acetone) 1,2-Dichloro- ethane Cyclopentane 2,3-Dimethyl- 2-butene O Equivalent Equivalent Hydrogens Hydrogens
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Organic Lecture Series 3 – a molecule with 2 or more sets of equivalent hydrogens gives a different NMR signal for each set CH 3 CHCl Cl CC 3 HH O Cyclopent- anone (2 signals) 1,1-Dichloro- ethane (2 signals) ( Z )-1-Chloro- propene (3 signals) Cyclohexen e Equivalent Equivalent Hydrogens Hydrogens Organic Lecture Series 4 • Relative areas of signals are proportional to the number of H giving rise to each signal • Modern NMR spectrometers electronically integrate and record the relative area of each signal Signal Areas Signal Areas
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Organic Lecture Series 5 Chemical Chemical Shifts Shifts 1 H-NMR NMR RC H 2 OR (C H 3 ) 4 Si ArC H 3 H 3 RC C H RCC H 3 RO H RCH 2 O H H 2 R O O H 2 R R 3 C H R 2 N H H 2 R R 2 C=CRC H R 2 R 2 C=C H R H O RCO H O H 2 Cl H 2 Br H 2 I H 2 F Ar H O O R 2 C=C H 2 RCOC H 3 H 2 R ArO H 9.5-10.1 3.7-3.9 3.4-3.6 Type of Hydrogen 0 (by definition) Ch emical Shift ( δ ) 1.6-2.6 2.0-3.0 0.8-1.0 1.2-1.4 1.4-1.7 2.1-2.3 0.5-6.0 2.2-2.6 3.4-4.0 Ch emical δ ) 3.3-4.0 2.2-2.5 2.3-2.8 0.5-5.0 4.6-5.0 5.0-5.7 10-13 4.1-4.7 3.1-3.3 3.6-3.8 4.4-4.5 6.5-8.5 4.5-4.7 Organic Lecture Series 6 Chemical Shift Chemical Shift 1 H NMR H NMR
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Organic Lecture Series 7
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310-4 - CH 310 N T Th 2-3:30 LECTURE 4 Textbook Assignment...

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