chapter6 - Chapter 6 6.1 Calculate the degree of the...

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Chapter 6 6.1 Calculate the degree of the unsaturation in the following hydrocarbons: (a) C 8 H 14 ; (b) C 5 H 6 (c) C 12 H 20 (d) C 20 H 32 (e) C 40 H 56 Solution: (a) =2 (b) =3 (c) =3 (d) =5 (e) =13 6.2 Calculate the degree of the unsaturation in the following formula, and the draw as many structures as you can for each: (a) C 4 H 5 ; (b) C 4 H 6 ; (c) C 3 H 4 ; Solution: (a) =1 H 2 CC H H 2 C CH 3 H 3 H C H CH 3 H 2 C C CH 3 CH 3 (b) =2 H 2 H C H CH 2 HC C H 2 C CH 3 H 3 C CH 3 H 2 C H CH 3 (c) =2
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HC C CH 3 H 2 CC CH 2 6.3 Calculate the degree of unsaturation in the following formulas: (1) C 6 H 5 N 5 (2) C 6 H 5 NO 2 5 (3) C 8 H 9 Cl 3 3 (4) C 9 H 10 Br 2 1 (5) C 10 H 12 N 2 O 3 6 (6) C 20 H 32 ClN 5 6.4 Give the IUPAC name for the following compounds: (1) 3,4,4-trimethyl-1-pentene (2) 3-methyl-3-hexene (3) 4,7-dimethyl-2,5-octadiene 6.5 Draw structures corresponding to the following IUPAC names: (a)2-Methyl-1,5-hexadiene (b)3-Ethyl-2,2-dimethyl-3-heptene (c)2,3,3-Trimethyl-1,4,6-octatriene (d)3,4-diisopropyl-2,5-dimethyl-3-hexene (e)4-tert-Butyl-2-methylheptane Solution:
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(a) H 2 C C H 2 C H 2 C C H CH 2 CH 3 (b) H 3 CC C C H H 2 C CH 3 CH 3 CH 3 CH 2 CH 3 (c) H 2 C C C C H C H C H C H CH 3 CH 3 CH 3 CH 3 (d) H 3 C H C C C C H CH 3 CH 3 CH 3 CH H 3 C CH 3 CH H 3 C CH 3 (e) H 3 H H 2 C H C H 2 C CH 3 CH 3 C H 3 C CH 3 CH 3 6.6 Name the following cycloalkenes: (a) CH 3 CH 3 (b) CH 3 CH 3 (c) CH(CH 3 ) 2 Solution: (a) 1,2-Dimethyl-cyclohexene (b) 4,4-Dimethyl-cycloheptene (c) 3-Isopropyl-cyclopentene 6.7 Which of the following compounds can exist as pairs of cis-trans isomers? Draw each cis-trans pair, and indicate the geometry of each isomer. (a) H 3 CHC CH 2 (b) (H 3 C) 2 C CHCH 3 (c) H 3 CH 2 CHC CHCH 3 (d) (H 3 C) 2 ( C H 3 )CH 2 CH 3 (e) ClHC CHCl (f) BrHC CHCl Solution: (c) cis: H 3 CH 2 C H H CH 3 t r a n s : H 3 CH 2 C H CH 3 H
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(e) cis: CC Cl H H Cl t r a n s : Cl H Cl H (f) cis: Br H H Cl t r a n s : Br H Cl H 6.8 Name the following alkenes, including the cis or trans designation: (a) CH H H CH 3 CH 3 CH H 3 C H 3 C (b) H CH 2 H CH 2 CH 3 HC H 3 C H 3 C Solution: (a) cis-4,5-Dimethyl-2-hexene (b) trans-6-Methyl-3-heptene 6.9 Which member in each of the following sets has higher priority? (a) –H or –Br (b) –Cl or –Br (c) –CH 3 or –CH 2 CH 3 (d) –NH 2 or –OH (e) –CH 2 OH or –CH 3 (f) –CH 2 OH or –CH=O Solution: (a) –Br (b) –Br (c) –CH 2 CH 3 (d) –OH (e) –CH 2 OH (f) –CH=O 6.10 Rank the following sets of substituents in order of Cahn-Ingold-Prelog priorities. (a) –CH 3 , -OH, -H, –Cl (b) –CH 3 , –CH 2 CH 3 , -CH=CH 2 (c) –CO 2 H, -CH 2 OH, -C N, -CH 2 NH 2 (d) –CH 2 CH 3 , -C CH, -C N, -CH 2 OCH 3 Solution: (From High to low) (a) –Cl, -OH, –CH 3 , -H (b) -CH=CH 2 , –CH 2 CH 3 , –CH 3 (c) –CO 2 H, -CH 2 OH, -C N, -CH 2 NH 2 (d) -CH 2 OCH 3 , -C N, -C CH, –CH 2 CH 3
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6.11 Assign E or Z configuration to the following alkenes: Solution: C C Cl CH 2 OH H 3 C H 3 CH 2 C C C C C C C Cl H 3 CO CH 2 CH 2 CH 3 CH 2 CH 3 CN CH 2 NH 2 H 3 C H CO 2 H CH 2 OH H 3 C Z E Z E 6.12 Assign stereochemistry to the following alkene, and convert the drawing into a skeletal structure: Solution: CH 2 COOCH 3 Z 6.13
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This note was uploaded on 01/03/2010 for the course ENGINEERIN H851 taught by Professor Potter during the Spring '09 term at University of Aberdeen.

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chapter6 - Chapter 6 6.1 Calculate the degree of the...

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