CHEM1020 INTRODUCTORY CHEMISTRY-ORGANIC CHEMISTRY

SEMESTER II, 2009-2010 Dr. J. Badenock

UNIVERISTY OF THE WEST INDIES - CAVE HILL CAMPUS

DEPARTMENT OF BIOLOGICAL AND CHEMICAL SCIENCES
QUIZ #2 – MARCH 3, 2010

N NAME: ______ ANSWERS_____________________ ID NUMBER: __________________

1. Aspartame, shown below, is a low-calorie sweetener found primarily in the artificial

sweeteners NutraSweet® and Equal®. Circle and label the functional groups in the following
structures (do not include alkanes).

Amide

Carboxylic acid O
HO OCH3 Ester
N
O NH2 H O

Amine
[4 marks]

2. O is the structure of a

A. carbonate
B. lactol
C. lactam
D. cyclic anhydride
E. lactone

3. O has the following name:

A. diethyl carbonate
B. ethoxyethyl ketone
C. 3-oxopentanone
D. ethyl propionate
E. ethyl ethanoate (or ethyl acetate)

4. When Procaine, shown below, is treated with one equivalent of hydrogen chloride, the salt
formed is Novocain, a local anesthetic. Circle the site of reaction i.e. the most basic site.

O CH3
N
O CH3

H2N tertiary amine is most basic

Procaine
CHEM1020 INTRODUCTORY CHEMISTRY-ORGANIC CHEMISTRY
SEMESTER II, 2009-2010 Dr. J. Badenock

NAME: ______ ANSWERS_______________________ ID NUMBER: __________________

5. Circle the more acidic from the following pairs? Please explain your choice briefly.

O O
a. H Cl
OH
H Cl
H Cl
EWGs esp. α to the carboxylate cabon
OH
stabilize the conjugate base by induction

O Carboxylic acids are more acidic than

alcohols (hence their name) mainly because
OH the conjugate base carboxylate has two
b. OH
equivalent resonance forms. NB This has
not much really to do with the benzene ring.

O O

O O

[2 x 3 marks]

6. Draw SIX (6) of the NINE (9) compounds named in the boxes below. Where appropriate
give a specific example (i.e. no R groups allowed). Please place the appropriate number on
the line next to the box with your attempt.

ii. 18-Crown-6
O
iv. Tetrahydrofuran (THF)
N O O
OH O O
NC
O O O
i. An imine (any O
variation will do!) O vi. Acetic anhydride
iii. A cyanohydrin
(any variation will do!)
O
O O NH
N N
H HO OH
ix. A β -lactam
v. Pyridine or Pyrrole vii. A vicinal diol (any variation will do!)
viii. A ketal (any variation will do!)
[6 marks]

7. Circle the least reactive and box the most reactive compounds towards nucleophiles.

O O O O O O O

H3C CH3 H3C Cl H3C OCH3 H3C H H3C N(CH3)2 H3C O CH3
CHEM1020 INTRODUCTORY CHEMISTRY-ORGANIC CHEMISTRY
SEMESTER II, 2009-2010 Dr. J. Badenock

NAME: __ANSWERS____________________________ ID NUMBER: __________________

8. Choose the most appropriate reagent for the following transformations. Place the letter
corresponding to the best choice in the blank to the left of the conversion.

N A. NaBH 4, EtOH N
C O OR C OH
i. A
B. LiAlH4,
H
then H3O+

O A. MeBr OH

Cl OR Me
ii. B Me
B. MeMgBr

A. LiAlH4, H+
O O
OR
iii. B OEt H
B. DIBAL, H+

A. MnO2 O
iv. A OH
OR H
H3C B. Na2Cr2O7,
H2SO4 H3C
[4 x 2 marks]

9. Write a detailed reasonable mechanism for the following reaction.

+
H

O + O18
+ H2O 18 H cat + H2O
H3C H H3C H
HO18
H2O
+
H H3C H
OH2
OH OH
H3C H
H3C H H3C H OH
OH
18
18

18 H
H2O
[7 marks]
CHEM1020 INTRODUCTORY CHEMISTRY-ORGANIC CHEMISTRY
SEMESTER II, 2009-2010 Dr. J. Badenock

NAME: ______ ANSWERS_______________________ ID NUMBER: __________________

10. Draw the missing reagent and conditions or principle organic product expected from each of
the following reactions. Indicate stereochemistry where appropriate!

SOCl2
Me Me O Me Me O H2N Me Me O
Me OH Me Cl Me N
H

O O excess OH O
NaBH4
H OH H OH
H2O
O OH

O +
O
CH3CH2OH, H
OH O

H2N H2N

O + NHPh
PhNHNH2, H N
H3C CH3
H3C CH3

Br COOH

1. Mg, Et2O
2. CO2
+
(H3C)3C O 3. H3O (H3C)3C O
O

[7 x 2 marks]