Semester Two Final Examinations 2019 CHEM1221

Semester Two Final Examinations, 2019 CHEM1221 General, Organic and Biological Chemistry
Venue ____________________
Seat Number ________
Student Number |__|__|__|__|__|__|__|__|
Family Name _____________________

This exam paper must not be removed from the venue
First Name _____________________
School of Chemistry and Molecular Biosciences

EXAMINATION
Semester Two Final Examinations, 2019
CHEM1221 General, Organic and Biological Chemistry

This paper is for St Lucia Campus students.
Examination Duration: 120 minutes

For Examiner Use Only
Reading Time: 10 minutes
Question Mark
Exam Conditions:
B1
This is a Central Examination
This is a Closed Book Examination - specified materials permitted

B2
During reading time - write only on the rough paper provided
This examination paper will be released to the Library
Materials Permitted In The Exam Venue: B3
(No electronic aids are permitted e.g. laptops, phones)
Calculators - Casio FX82 series or UQ approved (labelled) B4
One A4 sheet of handwritten notes double sided is permitted
A simple unassembled molecular model building kit in an unmarked container

is permitted.
Materials To Be Supplied To Students:

Total ________
1 x Multiple Choice Answer Sheet
Instructions To Students:
Additional exam materials (eg. answer booklets, rough paper) will be

provided upon request.
PART A: Answer on multiple choice answer sheet

PART B: Answer on examination booklet in spaces provided
Write your name and student number on both the examination paper and MCQ
answer sheet
Page 1 of 27
Instructions for Completing your MCQ Answer Sheet

1. The MCQ answer sheet must be handled with care. [Do not curl, crease, fold, staple or pin.]
2. Use only HB or B pencils. Press firmly. [Do not use any H-grade pencil, ball-point pens, or ink pens.]
3. Print your surname and initials (without full stops) in the line of large boxes under the
headings SURNAME and INITS.
Shade in completely the corresponding box beneath each letter.
[If your surname consists of two or more words, is hyphenated (-), or has an apostrophe ('),
shade the blank box above the A at the top of the surname area.]
Repeat this procedure for STUDENT NUMBER.
4. Complete, in the space provided: COURSE CODE and DATE.
5. Complete the answer boxes by shading the appropriate box completely. Do not extend
the shading outside the box
area.
6. Do not leave any questions

out.
S
7. Take care when making
corrections. Erased marks
A
must be completely erased.
M
8. Ask for a new answer sheet if
you have made too many
erasures.
P
Check List L
• Have you completed the
Surname and indicated at least
E
one initial?
• Is your Student Number

indicated correctly?
• Have you indicated the Course

Code and the Date in the space
O
provided?
N
• Have you shaded ONE
response only to every multiple-
choice question on your exam
L
paper?
Y
• Have you completely erased all
unwanted marks?
Good Luck!
Page 2 of 27
SECTION A: MULTIPLE CHOICE QUESTIONS

(Answer on the MCQ answer sheet provided)
There are 30 multiple choice questions worth 1 mark each.
There is no penalty for an incorrect answer. Blank or incorrect answers receive
no marks.
A1) Which ONE of the following amines is the WEAKEST base?
A2) Which ONE of the following statements regarding esters is CORRECT?

(A) An ester can be prepared by heating an amide and an amine in the presence of
an acid catalyst.
(B) An ester can be prepared by the reaction of an acyl chloride with an ether.
(C) An ester can be prepared by heating a carboxylic acid and an amine in the
presence of an acid catalyst.
(D) An ester can be prepared by heating an aldehyde and an alcohol in the presence
of an acid catalyst.
(E) An ester can be prepared by heating a carboxylic acid and an alcohol in the
presence of an acid catalyst.
Questions continue next page
Page 3 of 27
A3) What would be the product of the following reaction?
Questions continue over the page
Page 4 of 27
A4) Which ONE of the following statements regarding the compound shown below is
CORRECT?
(A) The compound is an imine and can be prepared by the reaction of

cyclohexanone with propanamine.
(B) The compound is an amide and can be prepared by the reaction of
cyclohexanecarboxylic acid with propanamine.
(C) The compound is an amide and can be prepared by the reaction of
cyclohexanone with butanamine.
(D) The compound is a secondary amine and can be prepared by the reaction of
propanal with cyclohexanamine.
(E) The compound is an imine and can be prepared by the reaction of butanal with
cyclohexanamine.
A5) Nucleophiles typically react faster with aldehydes than they do with ketones. Which of
the following statements explain this?
I Ketones are deprotonated by nucleophiles but aldehydes undergo addition.
II The carbonyl carbon of the aldehyde is more electropositive than that of a
ketone.
III Aldehydes have more lone pairs of electrons than do ketones.
IV The carbonyl group of the aldehyde is less crowded than that of a ketone.
(A) I only
(B) II only
(C) III only
(D) II and IV only
(E) I and IV only
Page 5 of 27
A6) Consider the reaction shown below:
Which one of the following structures represents the MAJOR product?
A7) Consider the carbon-carbon bonds shown in the molecule below. Which list has the
circled bonds in the CORRECT order of bond length, from SHORTEST (left) to LONGEST
(right)?
(A) III, IV, II, V, I

(B) IV, V, I=II, III
(C) IV, V = I, II = III
(D) III, II, V, I, IV
(E) V, I, IV, II, III
Page 6 of 27
A8) Which ONE of the following statements is INCORRECT?

(A) Dehydration of an alcohol can proceed by either an E1 or an E2 mechanism,
depending on its structure.
(B) Alcohols will have lower boiling points than ethers of the same molecular mass.
(C) The hydroxy group (-OH) is a poor leaving group.
(D) (CH3CH2)2CHOH is classified as a secondary alcohol.
(E) Secondary alcohols will give the same product when reacted with either PCC
(pyridinium chlorochromate) or chromic acid.
A9) Which statement most accurately describes delocalized electrons?

(A) Electrons in a hybrid orbital.
(B) Electrons in a σ (sigma) bond.
(C) Electrons shared by more than two atoms.
(D) Electrons in a π (pi) bond.
(E) Electrons in a lone pair.
A10) Which ONE of the following is the first intermediate in the reaction between benzoyl
chloride (an acid chloride) and methanol?
Page 7 of 27
A11) Which ONE of the following statements is INCORRECT?

(A) Dimethyl ether can be heated in hydroiodic acid (HI) to produce iodomethane by
an SN1 reaction.
(B) The central oxygen in dimethyl ether is sp3-hybridised and has two lone pairs of
electrons.
(C) Only weak forces of attraction exist between dimethyl ether molecules in the
pure liquid phase.
(D) Dimethyl ether is partly soluble in water, as the partially negative ether oxygen
can form hydrogen bonds to the hydrogen atoms of water molecules.
(E) The two carbons in dimethyl ether will have partial positive charges.
A12) How many of the following compounds are S-enantiomers?
(A) None
(B) One
(C) Two
(D) Three
(E) Four
Page 8 of 27
A13) Which ONE of the following would be the cyclohexane-containing product of the
SECOND mechanism step of the reaction shown below?
A14) Which of the following compounds with the molecular structures shown would have
the HIGHEST boiling point?
Page 9 of 27
A15) Which of the following statements about epoxides is INCORRECT?

(A) Epoxides can be made by reaction of a halohydrin with base.
(B) Epoxides can be made by reaction of an alkene with a peroxy acid.
(C) Epoxides are reactive because of the strain in the ring.
(D) Epoxides contain a four-membered ring containing three carbon and one oxygen
atom.
(E) Arene oxides can rearrange to give phenols.
A16) Which ONE of the structures of aspartic acid shown below is predominant at pH 5?
Page 10 of 27
A17) Alanine has pKa values of 2.34 and 9.60. At pH 9.60 which ONE OR MORE of the
following structures will be the predominant alanine form(s) in solution?
(A) I will be the predominant species.

(B) I and II will be present in equal concentrations.
(C) III and IV will be present in equal concentrations.
(D) III will be the predominant species.
(E) IV will be the predominant species.
A18) Thymopeptin is a pentapeptide that was used as an immunostimulant drug provided

to AIDS patients in the early 80s. Below you can see its structure at physiological pH.
What is the primary structure of thymopeptin?
(A) Arg-Lys-Asp-Val-Tyr
(B) Lys-His-Asp-Ala-Ser
(C) Arg-Met-Val-Asp-Tyr
(D) Lys-Val-Thr-Asn-Phe
(E) Arg-Lys-Asn-Ser-Tyr Questions continue over the page
Page 11 of 27
A19) Which ONE of the following pairs of interacting amino acid residues might contribute
to a protein’s tertiary structure by forming stabilising electrostatic interactions at pH
7.4?
(A) Glycine and leucine
(B) Phenylalanine and tyrosine
(C) Lysine and arginine
(D) Glutamine and histidine
(E) Glutamic acid and lysine
A20) The molecular diagram below represents a parallel β-pleated sheet in a protein. Which
labels in the diagram indicate hydrogen bond(s)?
(A) I and II
(B) II and III
(C) II and IV
(D) III and IV
(E) I, II, III, and IV
Page 12 of 27
A21) A triglyceride contains lauric acid (12:0), linoleic acid (18:2) and palmitoleic acid (16:1)
chains. How many moles of H2 would be required to completely reduce this
triglyceride to a saturated molecule?
(A) None
(B) Two
(C) Three
(D) Four
(E) Six
A22) Which ONE of the following statements correctly describes the properties of fatty
acids:
(A) Saturated fatty acids with longer hydrocarbon chains have a higher melting point
than saturated fatty acids with shorter hydrocarbon chains.
(B) Saturated fatty acids have a lower melting point than unsaturated fatty acids.
(C) Cis double bonds in unsaturated fatty acids cause tighter packing of the
hydrophobic hydrocarbon chains.
(D) Double bonds in polyunsaturated fatty acids are almost always present at the
C-3 position.
(E) The majority of naturally occurring unsaturated fatty acids contain trans double
bonds.
Page 13 of 27
A23) Which ONE of the following is the structure of methyl β- D-riboside? The structure of
D-ribose is provided below:
Page 14 of 27
A24) Which ONE OR MORE of the following molecules is (are) the product(s) of the reaction
between β-D-galactose and ethanol under acidic conditions?
The structure of β-D-galactose is provided below:
(A) I only
(B) I and II
(C) III only
(D) I and III
(E) I and IV
Page 15 of 27
A25) Which ONE OR MORE of the following structure are epimers of D-glucose? The
structure of D-glucose is provided below:
(A) I only
(B) I and II only
(C) I, II, and IV only
(D) II and III only
(E) IV only
A26) Which ONE of the following oligonucleotide double strand sequences will possess the
lowest value of the melting temperature, Tm? (Note: only a single strand is shown.)
(A) GTCGAATTGCGCTTAA
(B) GCGCATCGACTAGCGG
(C) AACGTTAAGCTGTTAC
(D) CCCCGGGGTTTTAAAA
(E) ATATGCTAGATAATGA Questions continue over the page
Page 16 of 27
A27) Which ONE of the following statements about amylopectin is INCORRECT? The
structure of amylopectin is provided below:
(A) Amylopectin is a polysaccharide and a major component of starch.

(B) Amylopectin is composed of unbranched chains of D-glucose units joined by
α-1,4-glycosidic linkages.
(C) Amylopectin contains α-1,6-glycosidic linkages between D-glucose units.
(D) Amylopectin is a reducing sugar.
(E) Amylopectin is a glucopyranose polymer.
A28) Which ONE of the following statements about RNA and DNA is CORRECT?
(A) A guanosine contains ribose, guanine, and a phosphate group.
(B) A terminal phosphate group is found at the 5´ end of DNA.
(C) The DNA “backbone” involves an alternating sequence of sugar and base groups.
(D) RNA is more stable than DNA because the 2´-OH group of ribose in RNA can
hydrogen bond to oxygens in the phosphate ester and protect the
phosphodiester bond from being cleaved.
(E) Each non-terminal phosphate group carries a 2– charge.
Page 17 of 27
A29) Which ONE of the following intramolecular or intermolecular interactions between

the hydrocarbon chains in amphiphilic molecules is responsible for the formation of
micelles in water?
(A) Ionic interactions
(B) Covalent bonds
(C) Hydrogen bonding
(D) Hydrophobic interactions
(E) Electrostatic charge screening
A30) Which ONE of the following structures is L-glucose? The structure of D-glucose is given
below:
END OF SECTION A
SECTION B BEGINS OVER PAGE
Page 18 of 27
SECTION B: SHORT ANSWER QUESTIONS

(Answer these questions in the spaces provided.)
Total of 20 marks for Section B.
There are four questions, each worth 5 marks. Do not write in red pen in this
section.
B1.
a) Draw in the boxes provided the respective organic product or products of each
reaction.
(1 mark)
(1 mark)
Question B1 continue over the page
Page 19 of 27
b) Draw an enol tautomer of the following molecule in the box provided.
(1 mark)
c) Complete the following reaction with the required reagent and intermediate product
in the boxes provided. (PCC in DCM = pyridinium chlorochromate in dichloromethane.)
(2 marks)
Total B1: ______/ 5 marks

Questions continues over the page
Page 20 of 27
B2.
Complete the mechanism diagram below with
i. ALL required electron pushing arrows for steps shown surrounded by dotted
boxes, and
ii. by drawing the missing intermediate in the box with the solid line.

Page 21 of 27
B3.
a) Draw the tripeptide Ser-Arg-Phe at physiological pH (pH 7.4).
(4 marks)
b) Calculate the charge of the tripeptide you drew above at physiological pH. Show your
working.
(1 mark)
Page 22 of 27
B4.
a) Complete the following reaction scheme by drawing ALL of the products that are
formed in the box provided below.
(2 marks)
Question B4 continues over the page
Page 23 of 27
b) Maltose is a disaccharide that contains two D-glucose subunits connected by an

α-1,4´-glycosidic linkage. Draw the structure of maltose. The structure of α-D-glucose
is provided below:
(3 marks)
END OF EXAMINATION
DATA SHEET AND PERIODIC TABLE ON FOLLOWING PAGES
Page 24 of 27
Data Sheet:
Data Sheet continues over page
Page 25 of 27
Periodic Table on next page
Page 26 of 27
1 2
H He
1.008 The Periodic Table of the Elements 4.003
3 4 5 6 7 8 9 10
Li Be B C N O F Ne
6.941 9.012 10.81 12.011 14.007 15.999 18.998 20.179
11 12 13 14 15 16 17 18
Na Mg Al Si P S Cl Ar
22.989 24.305 26.981 28.085 30.974 32.066 35.453 39.948
19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36
K Ca Sc Ti V Cr Mn Fe Co Ni Cu Zn Ga Ge As Se Br Kr
39.098 40.078 44.955 47.88 50.941 51.996 54.938 55.847 58.933 58.69 63.546 65.39 69.72 72.61 74.922 78.96 79.904 83.80
37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54
Rb Sr Y Zr Nb Mo Tc Ru Rh Pd Ag Cd In Sn Sb Te I Xe
85.468 87.62 88.906 91.224 92.906 95.94 (98) 101.07 102.905 106.42 107.868 112.41 114.82 118.710 121.757 127.6 126.904 131.29
55 56 57 72 73 74 75 76 77 78 79 80 81 82 83 84 85 86
Cs Ba La Hf Ta W Re Os Ir Pt Au Hg Tl Pb Bi Po At Rn
132.905 137.33 138.905 178.49 180.948 183.85 186.207 190.2 192.22 195.08 196.966 200.59 204.383 207.2 208.980 (209) (210) (222)
87 88 89 104 105 106 107 108 109 110 111 112 113 114 115 116 117 118
Fr Ra Ac Rf Db Sg Bh Hs Mt Ds Rg Cn Nh Fl Mc Lv Ts Og
(223) 226.025 227.028
58 59 60 61 62 63 64 65 66 67 68 69 70 71
Ce Pr Nd Pm Sm Eu Gd Tb Dy Ho Er Tm Yb Lu
140.12 140.908 144.24 (145) 150.36 151.96 157.25 158.925 162.50 164.930 167.26 168.934 173.04 174.97
90 91 92 93 94 95 96 97 98 99 100 101 102 103
Th Pa U Np Pu Am Cm Bk Cf Es Fm Md No Lr
232.038 231.036 238.029 237.048 (244) (243) (247) (247) (251) (252) (257) (258) (259) (260)
Page 27 of 27

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Semester Two Final Examinations, 2019 CHEM1221 General, Organic and Biological Chemistry

Seat Number ________

Student Number |__|__|__|__|__|__|__|__|

Family Name _____________________

School of Chemistry and Molecular Biosciences

CHEM1221 General, Organic and Biological Chemistry

Examination Duration: 120 minutes

This is a Closed Book Examination - specified materials permitted

This examination paper will be released to the Library

Materials Permitted In The Exam Venue: B3

(No electronic aids are permitted e.g. laptops, phones)

Calculators - Casio FX82 series or UQ approved (labelled) B4

One A4 sheet of handwritten notes double sided is permitted

A simple unassembled molecular model building kit in an unmarked container

Materials To Be Supplied To Students:

Additional exam materials (eg. answer booklets, rough paper) will be

PART A: Answer on multiple choice answer sheet

Instructions for Completing your MCQ Answer Sheet

4. Complete, in the space provided: COURSE CODE and DATE.

6. Do not leave any questions

• Is your Student Number

• Have you indicated the Course

SECTION A: MULTIPLE CHOICE QUESTIONS

A1) Which ONE of the following amines is the WEAKEST base?

A2) Which ONE of the following statements regarding esters is CORRECT?

Questions continue next page

A3) What would be the product of the following reaction?

Questions continue over the page

(A) The compound is an imine and can be prepared by the reaction of

A6) Consider the reaction shown below:

Which one of the following structures represents the MAJOR product?

(A) III, IV, II, V, I

Questions continue over the page

A8) Which ONE of the following statements is INCORRECT?

A9) Which statement most accurately describes delocalized electrons?

Questions continue over the page

A11) Which ONE of the following statements is INCORRECT?

A12) How many of the following compounds are S-enantiomers?

Questions continue over the page

Questions continue over the page

A15) Which of the following statements about epoxides is INCORRECT?

Questions continue over the page

(A) I will be the predominant species.

A18) Thymopeptin is a pentapeptide that was used as an immunostimulant drug provided

Questions continue over the page

Questions continue over the page

Questions continue over the page

(A) Amylopectin is a polysaccharide and a major component of starch.

Questions continue over the page

A29) Which ONE of the following intramolecular or intermolecular interactions between

SECTION B: SHORT ANSWER QUESTIONS

Question B1 continue over the page

b) Draw an enol tautomer of the following molecule in the box provided.

Total B1: ______/ 5 marks

Total B2: ______/ 5 marks

Question B4 continues over the page

b) Maltose is a disaccharide that contains two D-glucose subunits connected by an

Total B4: ______/ 5 marks

Data Sheet continues over page

Periodic Table on next page

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