The infrared spectrumfkx ks,c9:b x 1c6wqi)mz0dj 4 of an organic compound is shown.

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

  What is the correct IUPAC name of d:ck yu hyj pqi*/d) )/(y f-aeu4)5cno+rggrthis molecule?

  Which of the following represent savcn j5tqy jtiw7-:l4tt ).+iny3 fq3 xturated compounds?
I. 3-methyl-1-butyne
II. Propanol
III.

  Which of the following statements is not cor;ags9 ao6;(samlm h;s rect for the class of organic molecule9s slh s;(gm oa6ma;;as?

  Which functional grouprl ye(l,+kz h4s are present in this molecule?

I. Amine
II. Ester
III. Ether

  Which molecule is correctly identified/rc qah3b .(wd as an amide?

  What functional groups are bo3 h50(dzq scyzth present in the following organic molecule?

1.Determine the missing name and structure xah(:n qc/ cnm,1/(a p vqun(tusing 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 9u cek bw:5s-s()ex zjof radiation as shown.-szx( :9euske)b jc5 w

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 wq 0c7*fjuvh/7ag+b agith two chiral centers is shown.

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

1.Complete the table below wit5gd vxel095nkh the missing 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 unsaturaua gv3k7x,t,k q -n.txted 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 hyr(me9q,qri.gic ua9a;6g4reaction are: h u96c i9ryqr ;.,qg( eg4imaa

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 molecxukq rrqe-/k0 z3,pn8k uvy28 ules 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 fo 3zs7+,kzgsp*u 2othv:l2u7v irp8jk llowing structural formula.



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 moleculewoevj4l6z c ,h4,ek;ms are structural isomers of each other?

  Which of the following compounds could rm;.r,qflyuzr-( s4o form a racemic mixture with (+)-menthol? o(y.srz;qrlr, f4um-

  Which row gives the correcoe3v6 c 5psdmp hn)/a5t number of peaks and integration values for the struc 5esp dan /hc5o)v6mp3ture below?

  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 ,u i+sjpg xq kz c5x;7,5y+ut7t bhy2cthree 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 compounpy ./f l1,1kn+viies-)ibcz q ds in a homologous series are shown.

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

Properties and behaviors of organic mo70wfp4k cy/4tv7g ur4x k-noklecules can be inferred using intermolecular cufkrw- ypno/ 7v4k 7xgkt044forces.
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 unit with the following structural fo)ipr4lr,n/c9 b7 pcv j12zcc prmula.


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 produces the following t 71e*hehn/kjIR spectrum. * 1/ntkhej e7h
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 found to contain major peaks at m/z jyhbpxrjv(, sm7k: ;t o9 8u2z2hx 3av102, 57, and 453vsh7o x hxr(: 92 2bkyzmp,jjtv;ua8.

Which of the following compounds could this spectrum belong to?

  The mass spectrum of compound X features a fragment sakzx-8ut fd uvs j5g :1z*q53ion peak at 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 complete combustion, carbon dioxide and water are ng y)po( 6b dpt,+ci/zthe only products. The equation for this reacti ndcg )6 +biy,tpp(/ozon is shown.
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, and oxygen ow+pf;ziu9s0b o) k ib)nly.
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