Chem 31 Probset First Exam

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CHEM 31 PROBLEM SET 1 1.

For the following molecule: H H H N C 6 8 C N 4 C H 1 C N 7 2 H 5 O


3

a) Identify the hybridization of each numbered atom. b) Identify the orbital location of each lone pair of atoms 1, 3, 5 and 6. c) Which N is in plane with C-4? 2. For the following molecule: H H N

H N

C C

C C

H H O a) Draw all acceptable resonance structures. b) Draw the hybrid structure. c) Identify the most and least stable resonance structure.
3. For the following pairs of molecules: H H H O C S H C C C 2 H 1 1 H O H H O 2 a) or H H H H H H C C H H C C H Cl C C 1 1 Cl H H H 2 2 H H b) or H H H H H H C H C C H C H H C H C C H H C H 1 H C C C 1 H 2 H C H 2 H C C H H H c) or A) Identify which molecule is more polar. B) Identify which molecule is longer. C) Identify which molecule has greater bond strength. 4. Predict the indicated bond angle (either very close to, less than or greater than a certain ) + a) the C-N-C bond angle in (CH3)2NH2 b) the C-O-C bond angle in CH3OCH3 c) the C-C-N bond angle in CH3CN

5. Draw all possible conformations of isobutyl chloride using Newman Projection and identify the most stable and least stable conformer. 6. Draw the most stable chair conformer of glucose O H H

H H H H H O O C C C H C

C H O C H O O H

H 7. Name the following compounds using the R,S or E,Z designations where necessary:

a)

b)

c) 8. Indicate whether each of the following pairs of compounds are identical or are enantiomers, diastereomers or constitutional isomers

a)

b)

c)

d)

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