PROB_SET_#1_(Dr._Rathke)

PROB_SET_#1_(Dr._Rathke) - CEM 351 Fall 2008 - Prof. Rathke...

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CEM 351 Fall 2008 - Prof. Rathke 1st Sample Problem Set (Chapters 1, 2, 3, 4, 5) 1. For the following molecule: N C Br O the number of sp3 carbons is: the number of sp2 carbons is: the number of sp carbons is: the hybridization of N is: the hybridization of O is: the number of σ bonds is: the number of π bonds is: the molecular formula is: 2. Calculate the formal charge on each atom in the following structure. CH 2 N N 3. For a carbocation, carbon radical and carbanion: a) How many unshared electrons are associated with the central carbon? b) How many σ bonds are attached to the central carbon? 4. How many of the methyl groups will occupy an equatorial position in the more stable chair conformation of the following molecules? Which configuration should be most stable of the four? CH 3 CH 3 CH 3 CH 3 CH 3 CH 3 CH 3 CH 3 CH 3 CH 3 CH 3 CH 3 CH 3 CH 3 CH 3 CH 3
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CEM 351 - Dr. Rathke, Fall 2008 – 1 st Sample Problem Set. ... page 2 5. a) Draw a Newman projection of the most stable conformation of 2–methylhexane down the C 2 –C 3 bond. b) Draw Newman projections of the two chair conformations of trans-1-ethyl-3- methyl-cyclohexane viewed simultaneously down the C 3 –C 4 and C 1 –C 6 bonds. c) Draw a wedge-dotted line structure for molecule X . H H H CH 3 H CH 3 H H X d) Draw a wedge-dotted line structure for molecule Y . CH 3 H H CH 3 Y
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CEM 351 - Dr. Rathke, Fall 2008 – 1 st Sample Problem Set. ... page 3 6. Give the isomeric relationship between the following pairs of molecules. Your choices are constitutional, configurational, conformational or identical. a) CH 3 H H CH 3 H CH 3 and CH 3 H CH 3 H CH 3 H b) and CH 3 CH 3 CH 3 CH 3 CH 3 CH 3 c) CH 3 H and CH 3 H CH 3 H H CH 3 d) H CH 3 H H H CH 2 CH 3 H H H H CH 3 and e) H CH 3 H H H CH 2 CH 3 H CH 3 H H CH 2 CH 3 H and f) CH 3 CH 2 CH 3 CH 2 CH 3 CH 3 and CH 2 CH 3
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CEM 351 - Dr. Rathke, Fall 2008 – 1 st Sample Problem Set. ... page 4 7. Which of the following olefins possess configurational isomers? a) 1-hexene b) 2–hexene c) 2–methyl–1–hexene d) 2–methyl–2–hexene e) 3–methyl–2–hexene f) 3–hexene 8. Which of the following represent Z–3-methyl–2–pentene? Which represent E–3–methyl–2–pentene?
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This note was uploaded on 10/21/2009 for the course CEM 351 taught by Professor Rathke during the Fall '08 term at Michigan State University.

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PROB_SET_#1_(Dr._Rathke) - CEM 351 Fall 2008 - Prof. Rathke...

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