Question 1

Which of the following elements is the defining element of organic chemistry?

Accepted Answer

carbon

Question 2

Which of the following is NOT considered to be an organic compound?

Accepted Answer

copper coil

Question 3

Given the following compound, which labeled proton (A, B, or C) is the most acidic?

$$\mathrm{\begin{array}{c} 	ext{A} \quad 	ext{B} \quad 	ext{C} \end{array}}$$

Accepted Answer

B

Question 4

The $$pK_a$$ value of ethanol ($$\mathrm{CH_3CH_2OH}) is $$approximately 16 and the $$pK_a$$ value of ammonia ($$\mathrm{NH_3$}) is $$approximately 38. Using this information, complete the following statement: Ethanol is approximately _______ times more acidic than ammonia.

Accepted Answer

$$10^{12}$$ times more acidic

Question 5

Which molecular orbital (MO), from the diagrams shown below, best explains that electrons can move throughout the molecule in allyl carbocation?

Accepted Answer

non-bonding MO of Diagram 2

Question 6

A Lewis base can be described as:

Accepted Answer

an electron pair donor

Question 7

Predict the position of equilibrium for the following acid-base reaction:

$$\mathrm{C_5H_5N + H_2O \rightleftharpoons C_5H_5NH^+ + OH^-}$$

Accepted Answer

reactants are favored

Question 8

Which of the following compounds is the strongest acid?

Accepted Answer

cyclohexanethiol

Question 9

Which of the indicated atoms in Seroquel possesses a delocalized lone pair?

Accepted Answer

both sulfur X and nitrogen Y

Question 10

Indicate the hybridization of sulfur X in the Seroquel molecule.

Accepted Answer

$$sp^2$$

Question 11

Indicate the hybridization of nitrogen Y in the Seroquel molecule.

Accepted Answer

$$sp^2$$

Question 12

What type of orbital does the lone pair of nitrogen Y occupy?

Accepted Answer

$$sp^2$$

Question 13

What type of orbital does the lone pair of nitrogen Z occupy?

Accepted Answer

$$sp^3$$

Question 14

Which of the following intermolecular forces is primarily responsible for the high boiling point of water compared to methane?

Accepted Answer

hydrogen-bonding

Question 15

What are the approximate bond angles of $$\alpha$$ and $$\beta in $$the following molecule?

$$\alpha = 109.5^\circ$$, $$\beta = 120^\circ$$

Accepted Answer

$$\alpha = 109.5^\circ$$, $$\beta = 120^\circ$$

Question 16

Which of the following is the correct way of showing the bond-line structure of $$\mathrm{CH_3CH_2CH(CH_3$)_2}$$?

Accepted Answer

A zig-zag line with a branch at the second carbon

Question 17

Why is a $$p-$$orbital represented with a shaded and un-shaded region?

Accepted Answer

to indicate the un-shaded region represents a 0% probability of electron density

Question 18

In many organic reactions, the counterions are not shown. Why is this the case?

Accepted Answer

they are spectator ions that are generally not involved in the reaction

Question 19

Electrons that participate in resonance are ________ and located in ________.

Accepted Answer

delocalized; p-orbitals

Question 20

Theobromine, the compound shown below, is present in both the cacao plant (chocolate) and in the leaves of the tea plant. Place the indicated nitrogen atoms in order of increasing basicity (least basic first). Hint: Generally, when comparing similar atoms, the more electron density on an atom, the more basic it is.

Accepted Answer

X \u003c Y \u003c Z

Organic Chemistry I: Fundamental Concepts and Applications – Exam 1 Study Guide

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