HW 1 - Mandatory Assignment - Organic Chemistry 1 - Spring Semester 2017 PDF

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Mandatory Assignment Organic Chemistry 1 Spring Semester 2017...

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Homework #1 Organic Chemistry

Name

1) Draw complete Lewis structure for each of the following molecules: (a) CH5N (contains a bond between C and N) (b) CH3NO2 (contains a bond between C and N but no bonds between C and O) (c) CH2O (d) CH2Cl2 (e) BrCN

2) Complete the Lewis structure, including all lone pairs, for the molecule below. You may assume that each atom has an octet and that there are no formal charges on any atom. All atoms are shown. H

H C

H

O

C

O H

H

C

N H

N

C

C

Cl

C H

C C

H

C

C

C

C

C C

H

H H

C C H H

C

3) Determine the formal charge of every atom in every species in the sequence of reaction steps below. For any nonzero formal charge, write the formal charge next to the atom. If the formal charge on an atom is zero, write nothing next to the atom. NH

NH2

HO

C

H O

C

3

H3C

2

H3C

CH3

CH3

NH2

NH2

H O

C

2

H3C

C

CH3

H3C

CH3

OH2 NH2 NH2 C

HO

H2 O

H3C

C

CH3

3

H3C

OH2

CH3

OH NH3

NH2

H3O

C H3C

HO

C H3C

CH3

2

CH3

OH

OH NH3

CH3

H3C

C

NH3

C H3C

CH3 OH

OH

CH3

H3C C OH

NH3

CH3

H3C C O

NH4

4) For each species below, (i) Draw all resonance contributors and (ii) draw its resonance hybrid. Make sure to use the curved arrows on each structure to indicate how you get to the next resonance contributor. (Note: If all lone pairs are not shown, you should draw them in) H C

CH HC CH HC CH

C

H

a)

H C

CH HC CH HC CH

C

H

b)

O H C O

N C H

c)

O

H C C

O H 3C

d)

C C H

CH2

5) For each of the following molecular species, label each non-hydrogen atom with its electronic geometry—either linear, trigonal planar, or tetrahedral.

N

a)

HN

O

b)

2

6) Draw the complete Lewis structure for the following line structure, including all carbons, hydrogens and lone pairs. N

7) The dash-wedge notation of D-glucose is shown below. Draw its dash-wedge notation after each of the indicated rotations has taken place. (a) 180

OHOH

o

H OH O

OH

OH

D-glucose (b) OH

OH

o

180

H OH O

OH

OH

D-glucose...