CHE 230: Organic Chemistry I

Instructor: Andy Mitchell

Study Guide #1 (CH 1-5)

These are past exam questions, but please use

this as a STUDY GUIDE ONLY. You should
also work end of chapter problems.
1) Draw the following clearly and label nodes:

p-orbital:

sp3-orbital:

2) Draw the best Lewis structure (two-dimensions only) for each of

the following molecules with two-electron bonds represented by a
single line. Include lone pairs and formal charges:

CH3CH2OH

[CH3CO2]−

CH3Br

1
3) Add a formal charge to each of the following molecules at the
appropriate atom in each:

4) Draw three possible isomers for C3H8O:

5) In relation to the molecule in the box, indicate if each structure is an

isomer, a resonance contributor, or neither:

2
6) Draw the best resonance contributor that correlates to the structure
given and show the movement of electrons with curved arrows on
the given structure only:

3
7) Draw the following molecules in three-dimensions using wedges
and dashes. Include empty orbitals, lone pairs, and formal charges
as necessary:

BF3

CH4

NH3

[BF4]−

8) Draw the skeletal structure corresponding to condensed:

(CH3)3C(CH2)4CH3

4
9) Label orbitals used for each bond with an arrow:

10) Predict the hybridization of each labeled atom:

H3C CH3 H N
CH3 H H
CH3 H

O
H CH3 H3C H
H O
H H

11) Based on electronegativity, draw a partial positive (δ+) and partial

negative (δ−) on each non-hydrogen atom below:

12) Show why 1,4-dichlorobenzene has no NET dipole:

5
13) Each of the following is a TRUE statement; explain by matching it
with the first letter of one of the four acidity effects: element (E),
inductive (I), resonance (R), or hybridization (H):

CH3CH3 is a weaker acid than H2C=CH2

CH3CH2OH is a weaker acid than CF3CH2OH

H2O is a stronger acid than CH4

CH3C(O)CH3 is a stronger acid than CH3CH2CH3

14) Fill in the appropriate terms below:

6
15) Add equilibrium arrows to the following reactions to indicate if
reactants or products are favored:

7
16) Draw the structure of the Brønsted conjugate acid:

17) Draw the Brønsted conj. base as a resonance hybrid:

18) Explain the pKa difference caused by an inductive effect primarily

with structural explanations and very few words:

8
19) Explain the pKa difference caused by a resonance effect primarily
with structural explanations and very few words:

20) Show all products in two-dimensions only (include formal charges

and lone pairs) after a single Lewis acid-Lewis base interaction
using no more than 2 curved arrows:

9
21) For each generic name, draw the functional group with all pertinent
bonds shown and a generic R group. There is no need to show lone
pairs:

carboxylic acid:

alcohol:

22) For each functional group, write the generic name:

10
23) Circle the compound with the highest boiling point:

24) Circle the compound with the highest melting point:

25) Assign IUPAC names to the following compounds:

26) Draw skeletal structures for each IUPAC name:

11
27) Draw a single molecule for the following descriptions (you should
have only one molecule for each and all three should be different):

a) Possesses ONLY van der Waals (VDW) forces:

b) Possesses BOTH van der Waals (VDW) and Dipole-Dipole (DD)

forces:

c) Possesses ALL of van der Waals (VDW), Dipole-Dipole (DD),

and Hydrogen Bonding (HB) forces:

12
28) Draw all three isomers of pentane, C5H12:

29) Draw cyclopentane and one other isomer of C5H10:

13
30) Using a single word above each example, label the specific type of
strain indicated by the arrows:

31) (a) Draw both chair conformers of methylcyclohexane with both the
methyl group and the hydrogen attached to that carbon in each
conformer, indicate which is more stable using uneven equilibrium
arrows (6 points) and (b) calculate the energy difference based on
the fact that one gauche interaction = 0.9 kcal/mol:

14
32) Draw the single most stable chair conformation corresponding to
each planar structure; you must show the proper orientation of all
groups including methyl, t-butyl, and H:

15
33) Draw the chair conformation that correlates to the planar structure
shown:

34) Circle the molecule that is less soluble in water and explain your
answer with one drawing and a very brief explanation:

35) Show both products (you do not need to show stoichiometry) for the
following reaction:

16
36) For the energy diagram of butane rotation, very clearly draw all six
Newman projections (1-6) in the space below the diagram and
circle all gauche conformations:

17
37) Draw the following molecule as two mirror images with wedges and
dashes and describe their relationship as enantiomers or identical:

38) What is the maximum number of stereoisomers

for the following molecule?

39) Assign priorities (1-4) and indicate R or S configuration at each

stereocenter:

18
40) Draw all stereoisomers of 2,3-dibromopentane and label one set of
enantiomers and one set of diastereomers:

Br

H3C CH3
Br

41) Draw all stereoisomers of 1,4-dimethylcyclohexane and label them

as enantiomers or diastereomers:

19
42) Consider the following single enantiomer with an
optical rotation (of plane-polarized light) of +45°:

a) What is the optical rotation of the opposite enantiomer?

b) What is the optical rotation of the racemic mixture?

c) What is the enantiomeric excess of a 95:5 mixture?

43) Draw BOTH products and label them as either enantiomers or

diastereomers:
Me
H NH2
OH

O
racemic mixture (R)-sec-butylamine
pKa ~ 5 pKa (conj. acid) ~ 11

20