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Prelim 1 practice questions 2011

Prelim 1 practice questions 2011 - Page 2 of 8 1(15...

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H Cl I CH 2 OCH 3 SCH 3 CH 3 O CH 3 CH 3 CH 3 A B C D 1. (15 points) (a) Using the IUPAC nomenclature rules, provide the correct name for the structure shown below. Page 2 of 8 (c) Indicate which of the alkenes A-D (has/have) the ( Z )-configuration. (d) Indicate the unsaturation number (UN) for testosterone, shown below. answer Br answer: O H H D H OH CH 3 (b) Use a skeletal formula to draw the structure of ( E )-3-ethyl-6-methyl-2-heptene. answer: (e) Indicate which of the following compounds (i)-(iv) are constitutional isomers. answer (i) (ii) (iii) (iv) answer CH 3 testosterone O
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2. (15 points) (a) Indicate the expected C-N-H bond angle (in degrees) found in (CH 3 ) 2 NH. Page 3 of 8 (d) Which of the carbocations below (is/are) likely to rearrange to a more stable carbocation? (b) Indicate the expected H-C-O bond angle (in degrees) found in H 2 C=O. answer : answer : (c) Indicate the expected C-C-C bond angle (in degrees) found in H 2 C=C=CH 2 . answer : H C H H H H H CH 3 H answer : (i) (ii) (iii) H (e) Which one of the following species (i) - (iv) is the m o s t r e a c t i
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