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chapter6 - 6 Alkenes Structure and Reactivity Based on...

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6. Alkenes: Structure and Reactivity Based on McMurry’s Organic Chemistry , 7 th edition
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2 Alkene - Hydrocarbon With Carbon-Carbon Double Bond Also called an olefin but alkene is better Includes many naturally occurring materials Flavors, fragrances, vitamins
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3
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4 Why this Chapter? C-C double bonds are present in most organic and biological molecules To examine consequences of alkene stereoisomerism To focus on general alkene reaction: electrophilic addition
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5 6.1 Industrial Preparation and Use of Alkenes Ethylene and propylene are the most important organic chemicals produced petroleum light hydrocarbons thermal cracking 750-950 ºC thermal cracking beta-cleavage mechanism shown on board
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6 6.2 Calculating Degree of Unsaturation Relates molecular formula to possible structures Degree of unsaturation : number of multiple bonds or rings Formula for a saturated acyclic compound is C n H 2n+2 Each ring or multiple bond replaces 2 H's
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7 Example: C 6 H 10 Saturated is C 6 H 14 Therefore 4 H's are not present This has two degrees of unsaturation Two double bonds? or triple bond? or two rings or ring and double bond
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8 How many degrees of unsaturation in the molecule below? A) One B) Two C) Three D) Four E) Five
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9 How many degrees of unsaturation in the molecule below? A) One B) Two C) Three D) Four A) Five
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10 Degree of Unsaturation With Other Elements Organohalogens (X: F, Cl, Br, I) Halogen replaces hydrogen C 4 H 6 Br 2 and C 4 H 8 have one degree of unsaturation Organoxygen compounds (C,H,O) - if connected by single bonds Ignore oxygens. These don't affect the total count of H's
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11 Organonitrogen compounds Nitrogen has three bonds So if it connects where H was, it adds a connection point Subtract one H for equivalent degree of unsaturation in hydrocarbon
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12 How many degrees of unsaturation in the following molecules? A) C 6 H 8 O B) C 8 H 8 O C) C 4 H 5 Br D) C 6 H 9 ON E) CO 2
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13 How many degrees of unsaturation in the following molecules? A) C 6 H 8 O (3) B) C 8 H 8 O (5) C) C 4 H 5 Br (2) D) C 6 H 9 ON (3) E) CO 2 (2)
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14 Count pairs of H's below C n H 2n+2 CH 2 =CH-CH=CH 2 (C 4 H 6 ) (2 degrees of unsaturation) Add number of halogens to number of H's (X equivalent to H) CH 3 CH 2 CHBrCH 2 CH 2 Br C 5 H 10 Br 2 Same as C 5 H 12 (saturated) Ignore oxygen atoms (oxygen links H) CH 3 CH 2 CH 2 OH C 3 H 8 O Same as C 3 H 8 (saturated) CH3CH2OCH3 C 3 H 8 O Same as C 3 H 8 (saturated) CH 3 COCH 3 C 3 H 6 O Same as C 3 H 6 ( 1 degree of unsaturation) Subtract N's and 1 hydrogen - they have two connections CH 3 CH 2 CH 2 NH 2 C 3 H 9 N Same as C 3 H 8 (saturated) CH 3 CH 2 CN C 3 H 5 N Same as C 3 H 4 (2 degrees of unsaturation) Summary - Degree of Unsaturation Rules
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15 6.3 Naming of Alkenes Name the parent hydrocarbon Number carbons in chain so that double bond carbons have lowest possible numbers Rings have “ cyclo ” prefix
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