Instructions • Use black ink or ball-point pen. • Fill in the boxes at the top of this page with your name, centre number and candidate number. • Answer all questions. • Answer the questions in the spaces provided – there may be more space than you need. Information • The total mark for this paper is 90. • The marks for each question are shown in brackets – use this as a guide as to how much time to spend on each question. • In the question marked with an asterisk (*), marks will be awarded for your ability to structure your answer logically, showing how the points that you make are related or follow on from each other where appropriate. • A Periodic Table is printed on the back cover of this paper. Advice • Read each question carefully before you start to answer it. • Show all your working in calculations and include units where appropriate. • Try to answer every question. • Check your answers if you have time at the end. You must have: Scientific calculator, Data Booklet, ruler Chemistry International Advanced Level UNIT 4: Rates, Equilibria and Further Organic Chemistry Time 1 hour 45 minutes WCH14/01 Pearson Edexcel International Advanced Level *P70967A0232* 2  SECTION A Answer ALL the questions in this section. You should aim to spend no more than 20 minutes on this section. For each question, select one answer from A to D and put a cross in the box . If you change your mind, put a line through the box and then mark your new answer with a cross . 1 This question is about proton NMR spectroscopy. (a) How many peaks are there in the low resolution proton NMR spectrum of 2-methylpropan-2-ol? (1) A one B two C three D four (b) Which compound has three peaks with relative peak areas of 3:2:1 in its low resolution proton NMR spectrum? (1) A propanal B propane C propan-1-ol D propan-2-ol (c) Which compound does not have a singlet peak in its high resolution proton NMR spectrum? (1) A butanoic acid B butanone C butanal D butan-1-ol (Total for Question 1 = 3 marks) Use this space for any rough working. Anything you write in this space will gain no credit. *P70967A0332* Turn over    3  2 The high resolution mass spectrum of an organic compound X has a molecular ion peak with m/ z = 58.0417 and another peak with m/ z = 29.0390. Which compound is X? [Ar values: H = 1.0078 C = 12.0000 O = 15.9949] A CH3COCH3 B CH3CH2CHO C CH3CH2CH2CH3 D CH3CH(CH3)CH3 (Total for Question 2 = 1 mark) 3 A high performance liquid chromatography (HPLC) system used a column with a non-polar stationary phase and a solvent of methanol and water. A mixture of octane, octanal and octan-1-ol was placed into the HPLC column. What is the order of retention times? A B C D Shortest retention time Intermediate retention time Longest retention time octane octanal octan-1-ol octanal octan-1-ol octane octane octan-1-ol octanal octan-1-ol octanal octane (Total for Question 3 = 1 mark) Use this space for any rough working. Anything you write in this space will gain no credit.