MASSEY UNIVERSITY Institute of Fundamental Sciences Chemistry

123.101 Chemistry and Living Systems 2011 Semester Test (20%)

NAME ID NUMBER:

TEST INFORMATION This test covers material presented in Units 1 and 2. Marks: This test will be marked out of FORTY (40). SECTION A - contains FIFTEEN (15) short answer questions worth FIFTEEN (15) marks. SECTION B - contains TWO (2) questions worth TWENTY FIVE (25) marks. Time: Answers: You should be able to complete this test in about 60 minutes, but you will be given 90 minutes. Please enter the answers in the spaces provided below the questions.

Totals Section A Section B Total

_________ _________ _________

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1101 123.101 Sem Test SECTION A (15 marks) All questions are of equal value.

1.

Draw the skeletal formula of 2-chloropropanal.

2.

Circle any trigonal planar sp 2 carbon atoms on the diagram you have drawn.

( )

3.

Draw the Newman projection for the anti staggered conformation of 1,2dibromoethane.

4.

Draw the resonance form resulting from the electron shift shown:
O

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1101 123.101 Sem Test The next five questions are based on the following two molecules:
O OH

5.

What kind of isomers are A and B?

6.

Give the major peaks in the IR spectra for A and B. (Use the correlation table given in the appendix).

7.

How many sets of chemically equivalent hydrogens are there in A? Draw them on the diagram.

8.

Mark any stereocentre(s) in A or B with an *.

9.

Compound B is more water soluble than A; why?

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1101 123.101 Sem Test 10. Provide the missing reagent(s) for the following reaction:
OH + O

11.

Give the major product of the following reaction:

HBr

12.

Provide the missing reagent(s) for the following reaction:

+ NO2

13.

Provide the missing reagent(s) for the following reaction:

O + H OH

14.

Provide the missing reagent(s) for the following reaction:

+ NH2 N H O

15.

Give the product of the following reaction:

1) NaNH2 2) I

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1101 123.101 Sem Test SECTION B (25 marks) 16. [15 marks in total]
O Y A O B Y Cl

(a)

[2 marks] The mass spectrum of one of the molecules, A or B, displays two peaks at 172.03 and 174.03 in a ratio of 3:1. Which compound is it and why?

b)

[2 marks] What atom(s) are represented by the letter Y? = 1, C = 12, N 14, O 16, C1 35 / 37, Br 79 / 81) = = = = (H

(c)

[4 marks] The 1H NMR spectrum of one of the compounds is given below. Which one is it? On the drawing of the molecule, circle the chemically equivalent hydrogens to show how you arrived at your answer.

Question 16 continued over page

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1101 123.101 Sem Test

Question 16 continued from previous page

(d)

[5 marks] Draw TWO different chair conformations of A. Label the substituents axial or equatorial. Circle the most stable conformation and justify your answer.

(e)

[2 marks] Draw a resonance structure of A.

17.

[10 marks in total] For the following scheme of the synthesis of the antispasmodic drug Bietamiverine:

O OH Cl Step 1 Cl

O Cl

HO

N Step 2

Step 3

O O N N

(a)

[1 mark] Provide the missing reagent(s) for Step 1.

Question 17 continued over page

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1101 123.101 Sem Test

Question 17 continued from previous page

(b)

[1 mark] Give the product for Step 2.

(c)

[1 mark] Provide the missing reagent(s) for Step 3.

(d)

[4 marks] Provide a mechanism for Step 2 and explain the role of the reagents.

(e)

[3 marks] Provide a mechanism for Step 3 bearing in mind that the rate of reaction is dependent on the concentration of both reagents.

++++++++

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1101 123.101 Sem Test

APPENDIX Typical Stretching Frequencies

Bond type single bonds to hydrogen

Group

Class of compound alkanes alkenes and aromatic compounds alkynes alcohols and phenols carboxylic acids

C H
C H

Frequency range 1 (cm ) 2850-3000 3030-3140

C H

3300 3500-3700 (free) 3200-3500 (hydrogen-bonded) 2500-3000 3200-3600 2550-2600 1600-1680 1500-1650 1600-1780

broad

N H S
double bonds

amines, amides thiols alkenes imines, oximes aldehydes, ketones, esters, acids, amides alkynes nitriles

C C C N C O

triple bonds

C C

2100-2260 2200-2400

C N

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1101 123.101 Sem Test

This page is for rough working only and will not be marked unless specifically requested.

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1101 123.101 Sem Test

This page is for rough working only and will not be marked unless specifically requested.

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