Below is the atom arrangement for the molecule with molecular formula C₂H₂Cl₂O

	H	O
H	C	C	Cl
	Cl

Place bonds and lone pairs so that each atom has access to an octet (or duet for H).

a) What is the total number of lone pairs in this molecule?

Enter a number.

1

b) How many single bonds are present in this molecule?

Enter a number.

2
c) Analyze the polarity of each bond. Which bond, other than the C-C bond, is the least polar one in the molecule? (Hint: Use Table 1.3.) 3 ---Select--- C-H C=O C-Cl
d) Which carbon has the most partial positive character? 4 ---Select--- second C (under the O) first C (under the H)

Imagine the following orbitals gradually approaching each other as indicated by the arrows so that they begin to overlap.

If two electrons with opposite spins reside in the overlap region, then which of the following is the true statement?

Open the editor below and draw the skeletal structure, where each atom obeys the octet/duet rule and no atom possesses a formal charge, for the molecule whose condensed structure is below.
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(a) (CH₃)₂CHCHCHC(CH₃)₃



(b) (CH₃)₃CC(CH₃)₂CHCHCH₃

Remember for skeletal structures you do not show hydrogens that are bonded to carbon (hydrogens bonded to any other atom must be shown). Also, carbon labels are not used - carbons are understood to be at vertices and at the end of "sticks".

Use the structure below to answer the following questions.

(a) Write the name of the parent.

Answer is not case sensitive.

1
(b) Give the IUPAC name. (Note: Do not forget to use commas to separate locant numbers from each other and to use hyphens to separate locant numbers from letters.)

Answer is not case sensitive.

2
(c) Give the molecular formula. (Type your answer using the format CxHy for C_xH_y.)

Answer is case sensitive.

3
(d) Give the number of each of the following found in the molecule above.
primary carbons

Enter an exact number.

4
secondary carbons

Enter an exact number.

5
tertiary carbons

Enter an exact number.

6
quaternary carbons

Enter an exact number.

7

Using the chair conformation skeleton below (and using the numbering scheme given), determine the most stable chair conformation of the following. (Select all that apply.)

(a) The methyl group occupies the axial / equatorial position and is angled up / down.

1

equatorial axial up down

(b) The tert-butyl group occupies the axial / equatorial position and is angled up / down.

2

down up axial equatorial

Use the Newman projection below to answer the following questions.

(a) Is this the most stable conformation of this molecule?

1

yes no    

(b) Open the JME editor below and draw the skeletal structure of this molecule.
Do not use the wedge tool or the "X" tool on the toolbar.




(c) Write the IUPAC substitutive name for the molecule above.

Answer is not case sensitive.

3

Draw the skeletal structure the bromoalkane (molecular formula given) that gives the alkene shown as the exclusive product of E2 elimination.
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A




B




C