Chemistry 104, Spring 2018 Name: ANSWER KEY

Quiz 1 [20 points] Score: / 20

Version 2 Section: _________________________

1. (3 pts) Indicate whether the following statements are TRUE or FALSE. Points

CIRCLE YOUR ANSWERS. # Correct /3

TRUE FALSE Butane has more carbon atoms than both ethane and pentane.

TRUE FALSE Constitutional (structural) isomers of hydrocarbons typically have different boiling points.

TRUE FALSE 3-Methyloctene contains a double bond.

2. (2 pts) Draw the bond-line representation (also called line structure) for CH3CH=C(CH3)CH(CH3)2
DRAW YOUR ANSWER IN THE “ANSWER” BOX.

ANSWER: Points

# Correct /2

+½ point for using rules for bond-line structures correctly. This is a hydrocarbon - should consist only of lines!
+½ point for correct number of carbons drawn.
+½ point for correct connectivity between carbon atoms (sigma bond framework; placement of methyl groups).
+½ point for double bond being in the correct place (between C2 and C3).
3. (4 pts) Which of the following molecules are constitutional isomers of the molecule at right?
CLEARLY CIRCLE THE MOLECULE(S) BELOW TO INDICATE YOUR ANSWER(S).

Cyclononane (CH3)3CCH=CHCH2CH2CH3

(CH3)3CCH2CH2CH2CH2CH3

Points
+1 point for each correct structure circled
- 1 point for each incorrect structure circled # Correct /4
Only 0, 1, 2, 3, or 4 points are given – no negative scores!

4. (2 pts) Open Response: What is the molecular formula of the following structure? Note: Give your answer in the form
of CxHyNz, where x, y, and z are integers.
WRITE YOUR ANSWER IN THE “ANSWER” BOX.

ANSWER: Points

0 2
C 6H 5N 3
Correct? or

No partial credit given for this problem.

Order of atoms doesn’t matter; okay to use condensed structure or other variation of molecular formula – as
long as CORRECT numbers of carbon atoms, hydrogen atoms, and nitrogen atoms are listed.
3. (2 pts) Draw the dash-wedge structure for chloroform, CHCl3.
DRAW YOUR ANSWER IN THE “ANSWER” BOX.

ANSWER: Points

H # Correct /2

C
Cl
Cl
Cl

+½ point for correct number of hydrogens, carbons, and chlorines drawn.

+½ point for using rules for dash-wedge structures correctly. All atoms and bonds are shown.
+1 point for correct 3D representation – including bond angles! For example, the structures below would NOT
earn this point:
H H
Cl
H
Cl
C C C
Cl Cl Cl
Cl Cl Cl Cl

4. (7 pts) Open Response: A synthetic steroid is shown below; use this structure to answer the following questions.
WRITE EACH ANSWER IN THE BLANK PROVIDED.

d c H

O
H
e

a. How many lone pairs of electrons are in this compound? 4 pairs

b. What is the hybridization of carbon a?_ sp2

c. What is the hybridization of carbon b? sp3

d. What is the bond angle indicated by label c? 109.5º (or < 109.5º)

e. What is the electron region geometry of carbon d? tetrahedral

f. What is the molecular geometry of carbon a? trigonal planar

g. What orbitals are involved in forming the C-C bond at label e? What types of bond(s) are formed?

A s bond is formed between the sp2 orbitals of each carbon atom. A p bond is formed between the
unhybridized 2p orbitals of each carbon atom.

Points
+1 point for each correct answer.
No partial credit given for the individual parts of this problem. (Each provided answer is graded # Correct /7
as either right or wrong.) All of the highlighted phrases in the answer to 4.g are required in
student answers to be considered correct.