MOLECULAR STRUCTURE Drawing Practice


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4 Targets: 1. 3-D Drawing

2. Condensed formula to Lewis structure

Molecular Structure 3. Functional Groups

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4. Isomers, including structure versus stereoisomers (p 4)

MOLECULAR STRUCTURE
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For each of the following molecules, draw their 3-D structure. You will usually need to have converted the condensed structure into a Lewis structure. Draw in all hydrogens. - For molecules involving lone-pairs, draw them with the lone pairs shown. While this may not be required for test questions, VSEPR is impacted by lone pairs, so they indirectly impact where atoms are located. For this exercise, try to show where in space the lone pairs will be. To do so, put a “double dot” on the end of a stick (in place), or wedge (in front) or hash (in back).

Guidelines for Drawing Models:

A. 3-D Perspective

1. Keep as many atoms as possible in a single plane (plane of the paper) by zig-

zagging. Connections within the paper are drawn with straight lines.

2. Use wedges to indicate atoms that are in front of the plane.

3. Use hashes to indicate atoms behind the plane.

B. For any tetrahedral atom, only 2 attachments can be in the plane, 1 must be in front,

and 1 behind.

-if the two in the plane are “down”, the hash/wedge should be up

-if the two in plane are “up”, the hash/wedge should be down.

-the hash/wedge should never point in same direction as the in-plane lines, or else

the atom doesn’t looks tetrahedral

-for polyatomic molecules, it is strongly preferable to NOT have either of the in-

plane atoms pointing straight up. Straight-up in-plane atoms do not lend

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themselves to extended 3-D structures.

Good! Look tetrahedral
1. ALKANE. butane, CH3CH2CH2CH3 -take the chain and wiggle around all the single bonds. -The most stable actual shape is the one with the carbons zig-zagged and co-planar. -Notice the symmetry possible.

Bad! These don' t look tetrahedral!

2. ALKANE. Pentane, CH3CH2CH2CH2CH3

Molecular Structure

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3. HALOALKANE. 2-bromobutane, CH3CHBrCH2CH3

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-notice that if the 4 carbons are co-planar zig-zagged,

the attached Br can’t be in the same plane.

-try to compare with a partner 2 cases in which

Br is in front versus behind. Are they the same

molecule, or isomers?

4. ALKENE. Draw both: a) trans-2-butene, CH3CH=CHCH3 and b) cis-2-butene
(trans means the two CH3 groups are on the opposite sides of the double bond; cis means they are on same side) -notice that not only the 2 double-bonded C’s but also the four atoms directly attached are all co-planar.
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5. ALKYNE. 2-butyne, CH3CCCH3 -draw Lewis structure first
6. WATER. H2O
7. ALCOHOL. Ethanol, CH3CH2OH

8. ETHER. Diethyl ether, CH3CH2OCH2CH3

Molecular Structure

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9. FORMALDEHYDE. CH2O.

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-for 9-16, make sure you draw the Lewis

structure before you build models and draw

the 3-D picture. If you don’t know the

connectivity, you have no chance!

10. ALDEHYDE. CH3CH2CHO.

11. KETONE. CH3CH2C(O)CH2CH3.

12. ACID. CH3CH2CO2H. T
13. ESTER. CH3CH2CO2CH3.

14. AMMONIA. NH3 15. AMINE. (CH3CH2)2NH

16. AMIDE CH3CONH2.

Molecular Structure

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SAME OR DIFFERENT? Classify the following pairs as “same” or “isomers”. Rules:

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1. Structures which can be interchanged or made equivalent by rotations around single

bonds are considered to be the same.

2. “Isomers” are things with the same formula that can’t be made superimposable by

simple rotations around single bonds.

(For class, we will eventually need to be able to distinguish “structural isomers” from

“stereoisomers”, so try to do that if possible. And within stereoisomers, by test two we’ll

need to distinguish between “enantiomers”, which are mirror image isomers; versus

“diastereomers”, which are cis/trans isomers.)

H Br

Br H

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Br

Br H

CH3 H H

H

Cl

Cl H

Cl

H

H Cl

H

H

Cl Cl

Cl

H

H Cl

H

H

Cl Cl

Cl

Cl

HH

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MOLECULAR STRUCTURE Drawing Practice