Organic Chemistry 221
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Chapter 1-5
lithium diethylamide
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Li N CH2 CH3
How many electrons does phosphorus (atomic number 15) have in its valence shell?
Lithium diethylamide contains both ionic and covalent bonds. Circle the ionic bond(s) in lithium diethylamide.
Draw the orbitals of a C=C double bond. Clearly label each bond type and indicate the type of orbitals involved in each bond.
Write valid Lewis structures for each formula below. Show all non-bonding electrons as dots.
CF2Cl2Freon 12 (a common refrigerant)
CO2 carbon dioxide
Determine the hybridization for the atoms in each structure at right.
B
: O:
The hybridization of the nitrogen atom (A) is ________.
..
H3C C N:
CH3–CH–C–O–H
The hybridization of the oxygen atom (B) is ________.
..
The hybridization of the oxygen atom (C) is _______.
E
D
A
+NH3
The hybridization of the carbon atom (D) is _______.
C
The hybridization of the carbon atom (E) is ________.
H O
H
H
The molecular formula C2H4O can be converted into three line-bond
O
(complete) structures that are consistent with valence rules,
H C C H
C C O H C C
H
as shown at right.
A.
B.
C.
H
H
H
H H
Which one of these structures is not consistent with
valence rules? Which atom(s) in the structure?
Propose at least three isomers that have the molecular formula C3H9N
Indicate which of the molecules have dipole moments and show the expected direction of the dipole moment.
O
Cl
Cl
Cl
Cl
CH2 CH3
H
H
C C
H
H
D.
H
HO
HO
9. What is the molecular formula of vitamin C:
O
O
O
A
C
O
HO
O
OH
Vitamin C H O
OH
10. Circle each functional group and name the family of compound in the steroid at right:
11. Classify the indicated atoms in the structure at right as 1˚, 2˚, 3˚, or 4˚:
Atom (A) is___. Atom (B) is___. Atom (C) is___. Atom (D) is___.
H
B
12. Draw a pair of isomers having the formula C5H12.
O
13. Draw a pair of isomers having the formula C5H12S.
14. Draw a pair of isomers containing different functional groups having the formula C5H12O
CH2CH2CH3
15. Determine the IUPAC name for the alkane at right.
16. Draw structures corresponding to each of the following names:
CH3CHCH2CHCHCH3
1-sec-butyl-2-ethylpentane (rename properly after drawing)
CH3CH2
CH3
3-cyclobutylpentane
4-(2,2-dibromoethyl)-3,5-dichloroheptane
17.
The hydrogens labeled b are equivalent to the hydrogens labeled______.
a b c d e f g
The hydrogens labeled_____are not equivalent to any other hydrogens in heptane.
CH3CH2CH2CH2CH2CH2CH3
The hydrogens labeled a are1°, 2°, 3° or 4°.
18. Draw one conformation of 2-methylpentane in Newman projection looking down the 2-3 bond. Do the same for 2-methyl-2-pentene.
19. Why are cyclobutane and cyclopentane rings puckered? Name two conformations of cyclohexane.
20. Indicate the axial or equatorial orientation of the groups
in trans-1,4-dimethylcyclohexane.
21. a) Label the axial (A) and equatorial (E) positions.
b) Illustrate 2 methyl groups in a 1,3-diaxial conformation.
22. Draw [3,3,1]-bicyclononane.
23. Assign the R and S configuration to each of the following chirality centers. Which two represent the same molecule.
Br Cl
CH 3
H
CH 3
H
H
CH 3
Br
Cl
CH 3 H
CH 3 CH 3
H
H
Cl
OH
Br
CH 3 H
H
CH 3
Cl
Br
24. Draw all the isomers of C3H5ClBr2 and identify any chirality centers. Draw the stereoisomers of those molecules in Fischer projection.
D