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CHE 230 Exam 1
Winter Quarter 2021
Please answer all of the questions as completely and concisely as possible in the spaces
Problem Solving Questions [76 points]
1.) Draw the molecules given below in skeletal structure in the boxes provided. [4 pts]
a. Label all functional groups indicated by arrows within each molecule on the lines
provided. [6 pts]
2.) Provide approximate pKa values in the boxes provided for the protons indicated by the
arrows. [5 pts]
3.) Match the functional group with its correct name from the choices given. Note: not all
choices will be used. [6 pts]
Names: acid chloride, alcohol, aldehyde, alkyl halide, amine, carboxylic acid, ester, ether,
ketone, nitrile, thioether
4.) Draw all possible resonance structures of the molecule shown below using curved
arrows to show electron movement. Then draw the hybrid resonance form. 
5.) For each question below, refer to the reaction provided.
a. Use curved arrows to show electron movement to get you to the intermediates
and products given. 
b. Circle the type of reaction depicted in the boxes above the reaction. 
c. Label each component as either electrophile (E+) or nucleophile (Nu-) or BL Acid
or BL Base as appropriate in the boxes below the reactants/intermediates. 
6.) For the pair of acids shown below
a. Draw the conjugate bases in skeletal structure. [4 pts]
b. Circle the most acidic compound [2 pts]
c. Identify which effect is responsible for the acidity. [2 pts]
7.) The instructions apply to all three reactions that follow.
a. Label the acid and the base. [6 pts]
b. Predict the products drawing the conjugate acids and bases in the indicated
boxes. [12 pts]
c. Use curved arrows to show how products are formed. [3 pts]
d. Indicate in which direction the equilibrium will lie. [3 pts]
8.) On the molecule drawn below, circle all hydrophobic regions and put a box around all
hydrophilic regions. [2 pts]
9.) Label all electrophilic regions/atoms in the molecule below with E+ and all nucleophilic
atoms/regions with Nu-. [2 pts]
a. How many polar bonds are there in this molecule? [1 pt]
Multiple Choice Questions/Fill Ins [24 points]
1.) For the set of molecules below, answer the following questions.
a. Circle the intermolecular forces displayed by the molecule. [6 pts]
b. Rank them in terms of increasing boiling point [3 pts]
2.) The following questions refer to the molecule below.
a. What is the molecular formula? ______________________ [1 pts]
b. Match the carbon labeled above with the correct number of hydrogens. Write the
letter on the line below next to the number of hydrogens. [4 pts]
1H ______ 2H ______
c. Draw a constitutional isomer of the molecule that contains a carbonyl. [2 pts]
3.) Which proton would be removed first in an acid-base reaction?
4.) The double bond in an alkene is made up of:
a. 1 sp2-sp2 hybridized σ bond and 2 π bonds formed from overlapping p orbitals
b. 1 sp2-sp2 hybridized σ bond and 1 π bond formed from overlapping p orbitals
c. 1 sp-sp hybridized σ bond and 2 π bonds formed from overlapping p orbitals
d. 1 sp3-sp3 hybridized σ bond and 1 π bond formed from overlapping p orbitals
5.) How many atoms are sp2 hybridized in the molecule shown?
6.) How many atoms are sp3 hybridized in the molecule shown?