ORGANIC CHEMISTRY

SAMPLE TEST ONE

1) Consider the isomeric hexenes , how many are capable of cis/trans isomerism
A) 3 B) 4 C) 5 D) 6 E) None

2) Give the number of lone pairs of electrons in H2NOH.

A) 0 B) 1 C) 2 D) 3 E) 4

3) The formal charge on nitrogen in the compound below is ________.

A) +2 B) +1 C) 0 D) -1 E) -2

4) How many sets of degenerate orbitals exist in the sulfur atom?

A) 0 B) 1 C) 2 D) 3 E) 4

5) How many carbon-carbon σ bonds are present in the molecule shown?

A) 1
B) 2
C) 3
D) 4
E) 5

6) Which of the following is closest to the C-O-C bond angle in CH3-O-CH3?

A) 180° B) 120° C) 109.5° D) 90° E) 160°
7) Which of the following are acceptable Lewis structures, including formal charges, for
nitric acid, HNO3?

A) A only
B) B only
C) C only
D) both B and C

E) A, B, and C

8) Which of the following is not a conjugate acid-base pair?

A) H2O, HO- B) H2O, H3O+ C) HSO4-, H2SO4 D) -OH, O2- E) NO3-, NO2-

9) Choose the strongest acid

A) H2O B) H2Te C) H2S D) H2Se E) CH4

10) The compound below is an adrenocortical hormone called cortisone. Which

functional group is not present in cortisone?

A) Alcohol B) Alkyne C) Alkene D) Ketone

11) What is the conjugate base of CH3NH2?

A) CH3NH3+ B) CH3NH- C) NH4+ D) NH2- E) B or D
12) When the orbitals of two hydrogen atoms combine to form a hydrogen molecule, how
many molecular orbitals are formed ?

A) One B) Two C) Three D) Four E) Five

13) How many resonance structures (including the one shown) are possible for the
indicated ion?

A) None B ) One C) Two D) Three E) Four

14) Identify the most acidic carboxylic acid.

A) ICH2COOH B) BrCH2COOH C) CH3COOH D) FCH2COOH

E) ClCH2COOH

15) Which of the molecules below can hydrogen bond to another of the same compound?
A) CH3CH2OCH2CH3
B) CH3CH2COOCH3
C) (CH3CH2)2CHOH
D) CH3CH2COCH2CH3
E) all of the above
16) Which of the following has the highest boiling point?

A)

B)

C)

D)

E)

17) In the structure below, the hybridization of the oxygen is ________ and the C-O-C
bond angle is ________.

A) sp2; 120°
B) sp2; <109.5°
C) sp3; 120°
D) sp3; <109.5°
E) sp; 120°
MCAT LO: MCAT2.2
18) Name the compound.

A) 2-cyclopentyl-4-methylhexane B) 5-cyclopentyl-3-methylhexane

C) 1-cyclopentyl-1,3-dimethylpentane D) 2-cyclopentyl-4-methylheptane

E) 5-cyclopentyl-3-methylheptane

19) What principle(s) or rule must be used to determine the correct electronic
configuration for carbon in its ground state?

A) Aufbau principle B) Hund’s Rule C) Pauli Exclusion Principle

D) A and B only E) All of the above

20) Which of the following is a true statement?

A) The stronger the acid the larger its pKa

B) The conjugate base of a strong acid is a strong base
C) Acid-Base reactions always favor the formation of the stronger acid and the stronger
base
D) Strong acids can have negative pKa values
E) Bronstead Acids need not contain hydrogen

21) Assuming materials of equivalent molecular weight, which class of compounds

would have the highest boiling point?

A) Ether B) Alcohol C) Aldehyde D) Ketone E) Alkyl Bromide

22) Identify the compound that cannot hydrogen bond with like molecules.
A) CH3NH2 B) (CH3)2NH C) (CH3)3N D) CH3OH E) CH3(CH2)10CH2OH

23) Which of the following is the most soluble in H2O?

A) CH3(CH2)10CH2OH B) CH2(OH)CH2CH2CH2OH C) CH3CH2CH2Cl
D) Propane E) Octane
24) Consider the three isomeric alkanes hexane, 2, 3-dimethylbutane, and 2-
methylpentane. Which of the following correctly lists these compounds in order of
increasing boiling point?
A) 2, 3-dimethylbutane < 2-methylpentane < hexane
B) 2-methylpentane < hexane < 2, 3-dimethylbutane
C) 2-methylpentane < 2, 3-dimethylbutane < hexane
D) hexane < 2-methylpentane < 2, 3-dimethylbutane
E) hexane < 2, 3-dimethylbutane < 2-methylpentane

25) How many constitutional isomers are possible for C6H14?

A) 4
B) 5
C) 6
D) 7
E) 8

26) The current definition of Organic Chemistry is:

A) The chemistry of compounds derived from living things.
B) The chemistry of the compounds derived from carbon
C) The chemistry of compounds containing carbon, hydrogen and oxygen
D) The chemistry of compounds derived from carbon and hydrogen
E) The chemistry of petroleum compounds

27) A compound contains 40% carbon and 6.67% hydrogen. It has a Molecular Weight of
60 What is its molecular formula.

A) C2H4O2. B) CH2O, C) C2H4. D) C4H8O4. E) CHO

28 The complete combustion of 1,1-Dimethylcyclobutane with excess oxygen will

produce which of the following as the major product?

A ) Carbon dioxide B) Carbon monoxide C) Carbon D) Ethylene E) Cyclohexane

29) Which of the following structures (a-e) is another resonance structure of the
following organic molecule?

e)

30) The father of organic chemistry is

A) Wohler B) Berzelius C) Eppendorf D) Kekule E) Paracelsus