Organic Compounds: Alkanes and Their Stereochemistry

Draw the structures of the following molecules:

(c) Glycerol, ${\mathbf{C}}_{\mathbf{3}}{\mathbf{H}}_{\mathbf{8}}{\mathbf{O}}_{\mathbf{3}}$, a substance isolated from fat and used in cosmetics;

it has an -OH group on each carbon.

Draw the structures of the following molecules:

(b) Ethylenimine,  ${\mathbf{C}}_{\mathbf{2}}{\mathbf{H}}_{\mathbf{5}}\mathbf{N}$, a substance used in the synthesis of

melamine polymers; it contains no multiple bonds.

Identify the functional groups in the following substances, and convert

each drawing into a molecular formula (red 5 O, blue 5 N).

Identify the functional groups in the following substances, and convert

each drawing into a molecular formula (red 5 O, blue 5 N).

Give IUPAC names for the following alkanes, and convert each drawing

into a skeletal structure.

Give IUPAC names for the following alkanes, and convert each drawing

into a skeletal structure.

Give IUPAC names for the following alkanes, and convert each drawing

into a skeletal structure.

Give IUPAC names for the following alkanes, and convert each drawing

into a skeletal structure.

Locate and identify the functional groups in the following molecules.

Locate and identify the functional groups in the following molecules.

Locate and identify the functional groups in the following molecules.

Locate and identify the functional groups in the following molecules.

Locate and identify the functional groups in the following molecules.

Question: Locate and identify the functional groups in the following molecules.

Predict the hybridization of the carbon atom in each of the following

Functional groups:

(c) Carboxylic acid

Draw the structures of the following molecules:

(a) Biacetyl, ${\mathbf{C}}_{\mathbf{4}}{\mathbf{H}}_{\mathbf{6}}{\mathbf{O}}_{\mathbf{2}}$, a substance with the aroma of butter; it contains no rings or carbon–carbon multiple bonds.

Draw structures that meet the following descriptions (there are many

Possibilities):

 (b) Two isomers with the formula  ${\mathbf{C}}_{\mathbf{4}}{\mathbf{H}}_{\mathbf{8}}{\mathbf{O}}_{\mathbf{2}}$

Draw structures that meet the following descriptions (there are many

Possibilities):

(a) Three isomers with the formula ${\mathbf{C}}_{\mathbf{8}}{\mathbf{H}}_{\mathbf{18}}$

Draw structures of the nine isomers of ${\mathbf{C}}_{\mathbf{7}}{\mathbf{H}}_{\mathbf{16}}$

There are seven constitutional isomers with the formula ${\mathbf{C}}_{\mathbf{4}}{\mathbf{H}}_{\mathbf{10}}\mathbf{O}$. Draw as many as you can.

Draw and name all monobromo derivatives of pentane  ${\mathbf{C}}_5{\mathbf{H}}_{11}\mathbf{Br}$.

Draw and name all monochloro derivatives of 2,5-dimethyl hexane ${\mathbf{C}}_8{\mathbf{H}}_{17}\mathbf{Cl}$ .

Give IUPAC names for the following compounds:

a.

b.

c.

d.

e.

f.

cis-1, 2-Dimethylcyclobutane is less stable than its trans isomer, but cis-1, 3-dimethylcyclobutane is more stable than its trans isomer. Draw the most stable conformations of both, and explain.

Explain why each of the following names is incorrect:

1. 2,2-Dimethyl-6-ethylheptane
2. 4-ethyl-5,5-dimethylpentane
3. 3-ethyl-4,4-dimethylhexane
4. 5,5,6-Trimethyloctane
5. 2-Isopropyl-4-methylheptane

Propose structures and give IUPAC names for the following:

1. A diethyldimethylhexane
2. A (3-methyl butyl)-substituted alkane

What are the relative energies of the three possible staggered conformation around the C-2, C-3 bond in 2,3-dimethyl butane?

Construct a qualitative potential energy diagram for rotation about the C-C bond of 1,2-dibromo ethane. Which conformation would you expect to be most stable? Label the anti and gauche conformations of 1,2-dibromo ethane.

Which conformation of 1,2-dibromoethane would you expect to have the largest dipole moment? The dipole moment of 1,2-dibromoethane is $\mathbf{\mu }\mathbf{=}\mathbf{1}\mathbf{.}\mathbf{0}\mathbf{D}$. What does this tell you about the actual conformation of the molecule?

Draw the most stable conformation of pentane, using wedges and dashes to represent bonds coming out of the paper and going behind the paper, respectively.

Draw the most stable conformation of 1,4-dichlorobutane, using wedges and dashes to represent bonds coming out of the paper and going behind the paper respectively.

For each of the following compounds, draw an isomer that has the same functional group.

a.

b.

c.

d.

e.

f.

Malic acid, ${\mathbf{C}}_4{\mathbf{H}}_6{\mathbf{O}}_5$, has been isolated from apples. Because this compound reacts with 2 molar equivalents of base, it is a dicarboxylic acid .

a) Draw at least 5 possible structures

b) If malic acid is secondary alcohol what is its structure?