copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved. [1]
(e(iii)) Deduce the identity of the unknown compound using the
previous information, the 1H NMR spectrum and section 27 of the data booklet. SDBS, National Institute of Advanced Industrial Science and Technology (AIST). [2] 2. [Maximum mark: 21] 21M.2.hl.TZ2.4 Organic chemistry can be used to synthesize a variety of products.
(a) Several compounds can be synthesized from but-2-ene. Draw
the structure of the final product for each of the following chemical reactions.
[2]
(b) Determine the change in enthalpy, ΔH, for the combustion of
(c) State the hybridization of the carbon I and II atoms in but-2-
ene.
[1] (d) Draw diagrams to show how sigma (σ) and pi (π) bonds are formed between atoms.
[2]
(e) Sketch the mechanism for the reaction of 2-methylbut-2-ene
with hydrogen bromide using curly arrows.
[3]
(f ) Explain why the major organic product is 2-bromo-2-
methylbutane and not 2-bromo-3-methylbutane. [2] Combustion analysis of an unknown organic compound indicated that it contained only carbon, hydrogen and oxygen.
(g(i)) Deduce two features of this molecule that can be obtained
from the mass spectrum. Use section 28 of the data booklet.
(g(iii)) Deduce the identity of the unknown compound using the
previous information, the 1H NMR spectrum and section 27 of the data booklet. SDBS, National Institute of Advanced Industrial Science and Technology (AIST).
[2]
(h(i)) Draw the stereoisomers of butan-2-ol using wedge-dash type
representations. [1]
(h(ii)) Outline how two enantiomers can be distinguished using a
polarimeter. [2] 3. [Maximum mark: 18] 19M.2.sl.TZ2.1 Ethyne, C2H2, reacts with oxygen in welding torches.
(a) Write an equation for the complete combustion of ethyne. [1]
(b(i)) Deduce the Lewis (electron dot) structure of ethyne. [1]
(b(ii)) Compare, giving a reason, the length of the bond between the carbon atoms in ethyne with that in ethane, C2H6. [1]
(b(iii)) Identify the type of interaction that must be overcome when
liquid ethyne vaporizes. [1]
Ethyne reacts with steam.
C2H2 (g) + H2O (g) → C2H4O (g)
Two possible products are:
(c(i)) Product A contains a carbon–carbon double bond. State the type of reactions that compounds containing this bond are likely to undergo. [1]
(c(ii)) State the name of product B, applying IUPAC rules. [1]
(c(iii)) Determine the enthalpy change for the reaction, in kJ, to
produce A using section 11 of the data booklet. [3]
(c(iv)) The enthalpy change for the reaction to produce B is −213 kJ. Predict, giving a reason, which product is the most stable. [1] (c(v)) The IR spectrum and low resolution 1H NMR spectrum of the actual product formed are shown.
Deduce whether the product is A or B, using evidence from
these spectra together with sections 26 and 27 of the data booklet.
Identity of product:
One piece of evidence from IR:
One piece of evidence from 1H NMR: [2]
Product B, CH3CHO, can also be synthesized from ethanol.
(d(i)) Suggest the reagents and conditions required to ensure a good
yield of product B.
Reagents:
Conditions: [2]
(d(ii)) Deduce the average oxidation state of carbon in product B. [1]
(d(iii)) Explain why product B is water soluble. [3]
4. [Maximum mark: 6] 18N.2.hl.TZ0.2 An organic compound containing carbon, hydrogen and oxygen has 62.02 % carbon and 10.43 % hydrogen by mass.
(a) Determine the empirical formula of the compound, showing
your working. [3]
(b) The infrared spectrum of the compound is shown. Deduce the
functional group of the compound.
[1]
(c) The mass spectrum of the compound is shown. Deduce the
relative molecular mass of the compound. [1]
(d) The compound could not be oxidized using acidifi ed
potassium dichromate(VI).
Deduce the structural formula of the compound. [1]
5. [Maximum mark: 1] 17M.1.sl.TZ2.29 What can be deduced from the following 1HNMR spectrum?
A. There is only one hydrogen atom in the molecule.
B. There is only one hydrogen environment in the molecule.
C. The molecule is a hydrocarbon.
D. There is only one isotope in the element. [1]
6. [Maximum mark: 10] 17M.2.sl.TZ1.5 This question is about carbon and chlorine compounds.
(a) Ethane, C2H6, reacts with chlorine in sunlight. State the type of this reaction and the name of the mechanism by which it occurs.
[1]
(b) Formulate equations for the two propagation steps and one termination step in the formation of chloroethane from ethane.
[3] (c.i) One possible product, X, of the reaction of ethane with chlorine has the following composition by mass:
carbon: 24.27%, hydrogen: 4.08%, chlorine: 71.65%
Determine the empirical formula of the product. [2]
(c.ii) The mass and 1HNMR spectra of product X are shown below. Deduce, giving your reasons, its structural formula and hence the name of the compound. [3]
(d) Chloroethene, C2H3Cl, can undergo polymerization. Draw a
section of the polymer with three repeating units. [1] 7. [Maximum mark: 14] 17M.2.hl.TZ1.6 This question is about carbon and chlorine compounds.
(a) Ethane, C H , reacts with chlorine in sunlight. State the type of
2 6
this reaction and the name of the mechanism by which it
occurs.
[1]
(b.i) Formulate equations for the two propagation steps and one termination step in the formation of chloroethane from ethane.
[3]
(b.ii) Deduce the splitting patterns in the 1H NMR spectrum of C2H5Cl. [1] (b.iii) Explain why tetramethylsilane (TMS) is often used as a reference standard in 1H NMR. [2]
(c.i) One possible product, X, of the reaction of ethane with chlorine
has the following composition by mass:
carbon: 24.27%, hydrogen: 4.08%, chlorine: 71.65%
Determine the empirical formula of the product. [2]
(c.ii) The mass and 1H NMR spectra of product X are shown below. Deduce, giving your reasons, its structural formula and hence the name of the compound. [3]
(c.iii) When the product X is reacted with NaOH in a hot alcoholic
solution, C2H3Cl is formed. State the role of the reactant NaOH other than as a nucleophile. [1]
(d) Chloroethene, C H Cl, can undergo polymerization. Draw a
2 3
section of the polymer with three repeating units. [1]
