Chemistry 140A (C. L.

Perrin) 1

Midterm Exam #1 October 19, 2009 2

Name (printed): _____________________________________________ 3

Signature (written): __________________________________________ 4

ID#: _______________ 5
Sector: Left Center Right Row #____ (Last = 16 Left,15 Center&Right) 6

TA: Carrie Gary Miao Nick OR 7

Section day & hour ____________ (to retrieve your exam) ! /200

Student on your left ________________________________________________ (or Aisle )

Student on your right ________________________________________________ (or Aisle )

Fill in the names and numbers above, and check the boxes above
Read the instructions below, but
DO NOT TURN THE PAGE UNTIL YOU ARE TOLD TO DO SO.

This is a long exam; be sure that you have all 3 pages. Questions are arranged approximately in
order of increasing difficulty. It is more important to answer them correctly than to answer all of them.
Each question is worth 30 points, except one marked with – is worth 20. Partial credit will be minimal, so
read the questions carefully and weigh your answers critically. THINK BEFORE YOU WRITE; most
answers require only a few well-chosen structures. Show connectivity unambiguously with Lewis/Kekulé
structures or with "condensed" structures (CHn abbreviations, not zigzag "bond-line"). BE SURE THAT
STRUCTURES SATISFY THE OCTET RULE (if possible), show all ATOMS and all FORMAL
CHARGES, and show all LONE PAIRS as : (not necessary on halogens).
Write ONLY your answers on these pages, in INK, in the BOXES provided. (If your answer
is outside the box, draw a prominent arrow to it from the box.) Use only as many boxes as are necessary.
Extraneous wrong answers may lose points. You are encouraged to use the reverse for scratch paper, in
order to plan your answer. Leave blank the box at the top right.
PLACE YOUR PICTURE ID IN PLAIN VIEW, NEXT TO YOUR EXAM.
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1. DRAW two all-octet Lewis/Kekulé structures for CH3CNO (neither of which has an atom with
formal charge of +2 or -2). Indicate which one is the major resonance form and which is minor.
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"#

major minor major minor

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2. MARK WITH AN X all boxes that correspond to a correct statement. (Notes: More than one box
may be correct. Do not guess: Total score = right - wrong, but not < 0.)

(a) The acid-base reaction of CH3O- + NH3 can produce

CH3OH + NH2- . CH2=O + NH4+ . CH2=O + NH4- .

(b) The equilibrium constant for this reaction is >> 1 . << 1 .

(c) because of: electronegativity , orbital hybridization , resonance , steric repulsion .

(d) Electron-pushing illustrates this reaction by taking an electron pair from

CH . O . N . NH .

3. GIVE a specific EXAMPLE, with MOLECULAR STRUCTURE (geometry unnecessary), of an

all-octet molecule (not an ion) with exactly four carbon atoms, only three of which are sp2-hybridized
(plus any number of other atoms). (Note: No partial credit.)
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4. The birth of lambs with a single eye in the middle of their forehead ("cyclopism") has been found to be
due to an alkaloid, 11-deoxojervine (structure below), in a corn lily that pregnant sheep ate on day 14
of gestation. NAME the CLASSES to which 11-deoxojervine belongs because of its functional
groups. Use as many lines as necessary.

O
HN

OH
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5-. On the templates provided DRAW two different staggered conformations and one eclipsed
conformation about the C2-C3 bond of 2-methylbutane. Also CIRCLE the most stable.
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6. DRAW all different constitutional isomers of C6H 13Cl from the monochlorination of 3-methyl-
pentane (in as many boxes as necessary). Do not duplicate; repeated structures will lose points.
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7. [Note: This question covers material that is omitted in 2010.] DRAW the structures of the transition
states (geometry unnecessary) for the two propagation steps (in either order) in the chlorination of
chloromethane to dichloromethane, with dotted lines to represent partial bonds. You may omit $·.
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