The infrared spectrum of an orkap +6vwc 3an*k.ypy3 ganic compound is shown.

What are the units of the variable X, shown on the $x$-axis of the infrared spectrum?

  What is the correct IUp(exvk*l,uxw4:be a tb*x o**PAC name of this molecule?

  Which of the following represent saturaj ,zu7h:m kz7lted compounds?
I. 3-methyl-1-butyne
II. Propanol
III.

  Which of the following statements is not correct for the clas1s1 97xbacx/2z ouo lss of organic moleculeoa1 s2x7 l/c19obxuzs s?

  Which functional groups are prese,isa51,d xu urnt in this molecule?

I. Amine
II. Ester
III. Ether

  Which molecule is comg.fs6 pxk7(ut k;dl :rrectly identified as an amide?

  What functional groups are both present in the following organic moleculed g5zj-ah;qq2 ?

1.Determine the missing name and structag pfu.la4z);: 8i ry :m;tbxxure using IUPAC naming rules.
IUPAC Name Structural formula
2,3-dimethylbutane


2.Determine whether the following molecules are primary, secondary or tertiary halogenoalkanes.
Molecule Primary, secondary or tertiary
$CH_3CHClCH_2CH_3$
2-bromo-2-methylbutane

  The electromagnetic spectrum is divided into different types of radiation t6 i wv,-lr ( u78jzezgu3c8zias shoz civu,z3 zwu i7r t(e6-g88jlwn.

In one spectroscopic technique, electromagnetic radiation is used to identify functional groups based on the vibrational frequencies of their chemical bonds. Which of the following wavelengths of electromagnetic radiation would be most useful for this technique?

  A 3D model of a molecule tkew-p+z*p j+c. 8yo bwith two chiral centers is shown.

Which structural formula correctly illustrates the arrangement of bonds in this molecule?

1.Complete the table below with the mi1cayck6) 1wvxrvbc+ 5p.rr,op,0 aeussing formulae or structures.

Molecular name	Empirical formula	Molecular formula	Structural formula
Ethene
Butanoic acid

2.Name and give correct structural formula for 2 isomers of $C_3H_6O_2$ hat contain a carbonyl group.

  Which of the following is an example of uc4p:ivzs .8kvnsaturated hydrocarbons?

I. $CH_4$​
II. $CH_3Cl$
III. $C_2H_4$​
IV. $C_2H_2$​

  Compound X has a molecular mass of 148.
The mass spectrum of compound X contains a peak at m/z = 117.
Which of the following spectral fragments is lost from compound X to produce this peak in the mass spectrum?
Atomic masses (amu) C=12C=12, H=1H=1, O=16O=16

  The respective names of the monomer and polymer in the below polymerization r c2v 6bg0ewol-eaction argeo-bv2w c60le:

Compounds X and Y have the following structural formulas.


1.The IR spectrum of compound Y features a signal that is not present in the IR spectrum of compound X. Using section 26 (section 20- 2025 Syllabus) of the data booklet, state the range of wavenumbers in which this IR signal occurs.
2.The $^1H$NMR spectrum of compound X was recorded using electromagnetic radiation with a wavelength of $1m$.
The spectrum contains two signals with chemical shifts of 3.47 and 1.21 $ppm$. The integral of the signal at $1.21ppm$ is set to a value of 1.
(1)State the type of electromagnetic radiation used in this experiment, using section 3 (section 5- 2025 Syllabus) of the data booklet.
(2)Calculate the integral of the signal at $3.47ppm$.
(3)Suggest two features that would be present in the $^1H$NMR spectrum of Y but not in the spectrum of X, using section 27 (section 21 NS) of the data booklet.
3.The mass spectrum of one of the compounds is shown.



1.State the $m/z$ value of the molecular ion peak.
2.Explain how the identity of the compound can be determined from the peak at $m/z$ = 43, using section 28 ($section 22- 2025 Syllabus$) of the data booklet.

  Which of the following molecun.w2ydr 1a+wsles contains a tertiary amine?

The IR and $^1H$ NMR spectra of compound C are shown.



Compound C contains one $CH_3$ group and one functional group. The $^1H$ NMR signals of the compound do not change if a base is added to the NMR sample.
1.Using section 27 ($section 21- 2025 Syllabus$) of the data booklet, determine the number of $CH_2$ groups in compound C.
2.Using sections 26 and 27 (sections 20 and 21- 2025 Syllabus) of the data booklet, identify the functional group in compound C. 3.Give two reasons for your answer.
4.Draw the full structural formula of compound C.
The empirical formula of compound C was confirmed by measuring its elemental composition. Using your answer to (c) and section 6 (section 7- 2025 Syllabus) of the data booklet, calculate the expected abundance of carbon as a percentage of the molar mass.

  A carboxylic acid has the following structural formula clbqc) f,bg p.0wx85i.



The $^1H NMR$ NMR spectrum of the carboxylic acid is measured. Which of the following correctly describes the pattern of signals in the $NMR$ spectrum?

  Which pairs of molecules are structural ibq yq;l:eq4hx0 61 rmt+gbdqgpu8-n1somers of each other?

  Which of the following compoundunhk k,:+wtnu wmm63. s could form a racemic mixture with (+)-menthol? unn,k6hm tw.k3mu:+ w

  Which row gives the correct number of peaks and integration va86xle2 4g9;xzk jxqww+h*yx ilues for the structure bel i26ywj*g;w9e4 xx +zxlqh8kx ow?

  The $^1H$ NMR spectrum of compound A is shown.

Which of the following is a possible structural formula of compound A?

  The structural formulae of thrkqkhd+ z6wx6jd n bb,7c4 0;vcee compounds are shown.

A student measures the optical activities of the three compounds using a polarimeter. Which of the following results are they most likely to obtain?

  The structural formulas of two compounds in a ho,v3zuc 6dabw 8mologous series are shown.

Why does the boiling point of compound Y differ from that of compound X?

Properties and behaviors of organic movt+ uss *.xa,wlecules can be inferred using intermolecular forca*xst ,.uw+v ses.
Explain, giving a reason, which of the following pairs will have a higher boiling point:
1.Propane, butane.
2.Ethanol, ethanoic acid.
3.Propanol, propanone.

Compound A is a drug historically used for the treatment of insomnia. It consists only of carbon, hydrogen and oxygen atoms.
1.The IRIR spectrum of compound A contains a weak signal at $−12116\,cm^{−1}$ and a strong broad signal at $13450\,cm^{−1}$. There are no strong signals between 1500 and $12000\,cm^{−1}$.
State the names of the two functional groups present in compound A, using section 26 ($Section 20- 2025 Syllabus$) of the data booklet.
2.The mass spectrum of compound A is shown.

(1)State the $m/z$ value of the molecular ion peak.
(2)Using section 28 ($Section 22- 2025 Syllabus$) of the data booklet, suggest how the fragment ion peaks with $m/z$ values of 69 and 83 are formed.
3.The $^1H\,NMR$ spectrum of compound A is shown.


(1)Using section 27 ($Section 21- 2025 Syllabus$) of the data booklet, explain the relative sizes of the integrals for the signals at 0.96 and $2.86\, ppm$.
(2)Explain the splitting patterns of the signals centred around 0.96 and $1.64ppm$. 4.Based on your answers to (a), (b) and (c), draw the full structural formula of compound A.

A polymer P has a repeat unv*k: 8to1ovl a 3sv/d8nny zf-it with the following structural formula.


1.State whether the carbon atom labelled with an asterisk (*) is primary, secondary or tertiary, giving a reason for your answer.
2.Polymer P is produced via the addition polymerisation of compound A.
(1)Draw the full structural formula of compound A.
(2)Compound A has two structural isomers that contain the same functional groups. State the IUPAC names of compound A and both structural isomers.
(3)State the observation when compound A is mixed with aqueous bromine.
(4)An organic compound can also be identified by measuring the mass of carbon dioxide and water produced when each gram of the compound undergoes complete combustion. The equation for the combustion of another compound B is shown.
$B$ +12 $O_2$ →8 $CO_2$+8 $H_2O$Explain why compound A could not be distinguished from compound B using this method.

  Compound Y has the molecular formula C4H8O2CX​HX​OX​ and bgm vm2; x(tl(produces the following IR sv(b(t ;xl2gmmpectrum.
Which gives a possible structure for Y?
($IR\,absorptions: C=O: 1700−1750\,cm^{−1}$;
O−H ($alcohol$): 3200−3600 $cm^{−1}$ ($broad$);
O−H ($carboxylic acid$): 2500−3000 $cm^{−1}$ ($very broad)$)

  The mass spectrum of an alcohol was founwplb1 8 b-//guq-mjg;4d drdnd to contain major peaks at m/z 102, 57, and 4d1b j/8/w n;qmg-g 4dlrup-d b5.

Which of the following compounds could this spectrum belong to?

  The mass spectrum of compound X features a fragment ion peak azh0;k (fbkdmc n -d4mi 1)mkt2t an $m/z$value 31 units lower than the molecular ion peak.
The $^1H$ NMR spectrum of the compound is shown.


Which of the following is the most likely structural formula of compound $X$?
Atomic masses ($amu$):C=12, H=1H=1, O=16O=16

  The $^1H$ MR spectrum of alkane A is shown.

Which of the following is a possible condensed structural formula of alkane A?.

  When pentan-2-one undergoes co;:/tl,g: ndvcls/x7 xemav gx4-:ltf mplete combustion, carbon dioxide and water are the only products. The equation for this reaction is showg c slv /xag-t/n , 4xm;t::dxv7elf:ln.
Pentan-2-one+a $O_2$ →b$ CO_2$+$b H_2O$
What are the values of a and b in this equation?

Compound X contains carbon, hydrogen,5 .tvu 1yynmawo ib+17 and oxygen only.
1.Combustion of 50.0 $g$ of compound X in excess oxygen produced 107.8 $g$ $CO_2$, and 44.1 $g$ $H_2O$. Determine the empirical formula of compound X.


2.Using the mass spectrum above, state and explain the molecular formula of compound X.
3.A high-resolution mass spectrum of the same compound revealed a major peak at m/z = 57. Refer to section 28 ($Section 22- 2025 Syllabus$) of the Data Booklet to deduce the identity of the ion responsible.

4.Use Section 26 ($Section 20- 2025 Syllabus$) of the Data Booklet to identify the bonds responsible for peaks I and II on the IR spectrum above.
5.The peaks and relative intensities for the 11H NMR spectrum are given in the table below. Use Table 27 ($Section 21- 2025 Syllabus$) of the Data Booklet and your answers to (b), (c) and (d) to deduce the structure of X.
Chemical shift (ppm) is 0.9 ; Relative peak intensity is 6
Chemical shift (ppm) is 1.5 ; Relative peak intensity is 1
Chemical shift (ppm) is 2.2 ; Relative peak intensity is 2
Chemical shift (ppm) is 11.5 ; Relative peak intensity is 1