Description

FOUNDATION IN SCIENCE

SUBJECT: CHEMISTRY 3

SUBJECT CODE: FIS0354

TIME ALLOWED: 24 HOURS

DUE DATE: 17 APRIL, 2020 before 9 a.m.

SUBMISSION METHOD: Send via Blackboard

This examination question paper consists of six (6) printed pages including the cover page.

INSTRUCTIONS TO CANDIDATE:

1.                 Answer ALL questions.

Question 1

A)               Compound A, C6H12, was found to be optically active.  On catalytic reduction over a palladium catalyst, one equivalent of hydrogen was absorbed, yielding compound B, C6H14.  When compound A was treated with KMnO4 in an acidic condition, CO2 bubbled out and compound C was formed.  Compound C has the formula C5H10O2 and it is an optically active carboxylic acid.  Draw the condensed structural formula and state the IUPAC name of compound A, B and C.                                                                                                               (9 marks)

B)                            Answer the following questions according to Molecule R.

i)                    In the box above, draw skeletal structure and write the IUPAC name of the major SN1 product from the reaction of molecule R.              (3 marks)

ii)                  Show the mechanism for the formation of the product you drew in i).

(5 marks)

iii)                Consider the effect on the rate of the reaction when the following changes are made to the SN1 reaction of molecule R.  Write either 'slower', 'faster', or 'no appreciable change' as appropriate.  Justify your answer.

a)   CH3OH changed to CH3CH2CH2OH                                      (3 marks)                  

b)      Ethyl group changed to phenyl group                                     (3 marks)

c)      Iodine changed to chlorine                                                      (3 marks)

iv)        Complete two (2) distinctly different reasons why the reaction of molecule R does not occur by an SN2 reaction.                                            (4 marks)

     (Total: 30 marks)

Question 2

A)                Answer the following questions according to the synthesis of compound 11.

i)       Draw a skeletal structure of the stereoisomer of alkene 6.                        (2 marks)

ii)      In compound 7, is the bromine bonded to a primary, secondary or tertiary carbon atom?                                                                                                           (2 marks)

iii)    Identify reagent A and B.                                                                         (2 marks)

iv)    Redraw compound 8 and indicate the α and β carbon atoms.                  (2 marks)

v)      Name and circle four (4) functional groups in compound 11.                 (4 marks)