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HL Paper 1

Which statement is correct for a pair of enantiomers under the same conditions?

A.  A racemic mixture of the enantiomers is optically active.

B.  They have the same chemical properties in all their reactions.

C.  They have the same melting and boiling points.

D.  They rotate the plane of plane-polarized light by different angles.




Which molecule has an enantiomer?

A.  CH3CH2CH(OH)CH2CH3

B.  CH2(OH)CH2CH2CH=CH2

C.  CH3CH2CH2CH=CHBr

D.  CH3CHBrCH2CH2CH3 




Which is correct for the conversion of propanal to propyl methanoate?




What will be the major product in the reaction between but-1-ene and Hbr?

A.  2-bromobut-1-ene

B.  1-bromobut-1-ene

C.  2-bromobutane

D.  1-bromobutane




Which molecule is chiral?

A.     2-chlorobutane

B.     2,2-dichloropentane

C.     Propan-2-amine

D.     4-hydroxybutanoic acid




Which is most likely to hydrolyse via a SN1 mechanism?

A.  CH3CHBrCH2CH3

B.  (CH3)2CHBr

C.  (CH3)3CBr

D.  CH3CH2CH2CH2Br




Which compound rotates the plane of plane-polarized light?

A.  CH3C(CH3)ClCH3

B.  CH3CH2CHClCH3

C.  CH3C(Cl)2CH3

D.  CH3CClBrCH3




In which order should the reagents be used to convert benzene into phenylamine (aniline)?




Which compound shows cis-trans isomerism?

A.  CH3CH=CCl2

B.  CCl2=CH2

C.  

D.  




What is the product of the reaction of benzene with a mixture of concentrated nitric and sulfuric acids?




Which reagents are needed to convert nitrobenzene to phenylamine in 2 steps?

M18/4/CHEMI/HPM/ENG/TZ1/37




Which molecule contains a chiral carbon?

A.     CH3CH2CHBrCH2CH3

B.     CH3CH2CHBrCH3

C.     CH2BrCH(CH3)CH2Br

D.     CH3CH2CH2CH2CH2Br




Propene is reacted first with hydrogen chloride to produce X which is then reacted with aqueous sodium hydroxide to give Y. Finally, Y is reacted with excess acidified potassium dichromate solution.

C H 3 CHC H 2 HCL X NaOH(aq) Y H + / C r 2 O 7 2 (aq) Z

What is the major product, Z? 

A.     CH3CH(OH)CH3

B.     CH3COCH3

C.     CH3CH2CHO

D.     CH3(CH2)2COOH




Which statement is correct about configurational isomers?


A.  Configurational isomers can only be interconverted by breaking and reforming bonds.

B.  Configurational isomers have different molecular formulas but the same structural formulas.

C.  Configurational isomers are not distinct compounds.

D.  Configurational isomers always have identical physical properties.




Which is the correct combination of substitution reaction mechanisms?

M18/4/CHEMI/HPM/ENG/TZ2/35




Which product is formed when CH3COCH2CH3 is reduced with sodium borohydride?


A.  CH3CH2CH2CHO

B.  CH3CH2CH2CH2OH

C.  CH3CH(OH)CH2CH3

D.  CH3CH2CH2COOH




What is the major product of the reaction of HBr with but-1-ene?

 

A.   1-bromobutane

B.   2-bromobutane

C.   1,2-dibromobutane

D.   2,2-dibromobutane




Which statement about the reaction of a hydroxide ion with the organic reagent is correct?

 

A.   1-bromopentane predominantly follows an SN1 mechanism.

B.   2-bromo-2-methylbutane predominantly follows an SN2 mechanism.

C.   Reaction with 1-bromopentane occurs at a slower rate than with 1-chloropentane.

D.   Reaction with 1-bromopentane occurs at a slower rate than with 2-bromo-2-methylbutane.




What is the product of the reaction of propanal with lithium aluminium hydride, LiAlH4?

A.  Propanoic acid

B.  Propanone

C.  Propan-1-ol

D.  Propan-2-ol




Which attacking species is matched with its mechanism of reaction?





What are the E/Z designations of these stereoisomers?




Which is a major product of the electrophilic addition of hydrogen chloride to propene?

A. ClCH2CH=CH2

B. CH3CH(Cl)CH3

C. CH3CH2CH2Cl

D. CH3CH=CHCl




Which class of compound is formed when a ketone is reduced?

A. primary alcohol

B. secondary alcohol

C. ether

D. carboxylic acid




Which compound exists as two configurational isomers?

A. CBr2=CH2

B. CH2=CHBr

C. CHBr2CH2Br

D. CHBr=CHBr




Which can show optical activity?

A.  CHBrCHCl

B.  CH3CH2CHBrCH2CH3

C.  (CH3)2CBrCl

D.  CH3CH2CH(CH3)Br




Which pair of isomers always shows optical activity?

A.     Cis-trans

B.     Enantiomers

C.     Conformational

D.     E/Z




Which can be reduced to an aldehyde?

A. Butanone

B. Butan-1-ol

C. Butanoic acid

D. Butan-2-ol




Which isomers exist as non-superimposable mirror images?

A.     cis-trans isomers

B.     diastereomers

C.     enantiomers

D.     structural isomers




What is name of this compound applying IUPAC rules?

M18/4/CHEMI/HPM/ENG/TZ1/X35

A.     E 1-bromo-1-chlorobut-1-ene

B.     Z 1-bromo-1-chlorobut-1-ene

C.     E 1-bromo-1-chloro-2-ethylethene

D.     Z 1-bromo-1-chloro-2-ethylethene




Propene reacts separately with H2O/H+ and H2/Ni to give products X and Z respectively. 

What are the major products of the reactions?




What is the product of the reaction between pentan-2-one and sodium borohydride, NaBH4?

A. Pentan-1-ol

B. Pentan-2-ol

C. Pentanoic acid

D. Pentanal




Which is the electrophile in the nitration of benzene?

A.  HNO3

B.  NO2+

C.  NO2-

D.  NH4+




What is molecule Z that is formed in step 1 of this synthetic route?




What is the product of the reduction of 2-methylbutanal?

A.     2-methylbutan-1-ol

B.     2-methylbutan-2-ol

C.     3-methylbutan-2-one

D.     2-methylbutanoic acid




Which solvent is aprotic?

A. H2O

B. C6H5CH3

C. CH3OH

D. CH3NH2




What is the number of optical isomers of isoleucine?

A. 0

B. 2

C. 4

D. 8




How many chiral centres are there in the following molecule?

A.  2

B.  3

C.  4

D.  6




Which sequence of reagents converts propene to propanone?




Which compound can exist as cis- and trans-isomers?




In which compound is the halogen substituted the most rapidly by aqueous hydroxide ions?

A. (CH3)3CCl

B. (CH3)3CI

C. CH3CH2CH2CH2Cl

D. CH3CH2CH2CH2I




How many chiral carbon atoms are present in one molecule of (CH3)2CHCHClCHBrCH3?

 

A.   0

B.   1

C.   2

D.   3




Which statement is not correct regarding benzene?

A. It is planar.

B. The ring contains delocalized electrons.

C. It always reacts in the same way as alkenes.

D. The carbon–carbon bond has a bond order of 1.5.




What are the type of reaction and role of the nitronium ion, NO2+, in the following reaction?

C6H6 + NO2+ → C6H5NO2 + H+