Chemistry 101 Practice EXAM ANSWERS

7/23/2019 Chemistry 101 Practice EXAM ANSWERS

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Practice exam

ANSWERS

The answers provided are a rough guide only, in many cases more will beexpected from you in the exam to justify the marks associated with eachquestion.

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Question 1 [11 marks](a) Amprenavir is a drug used to treat HIV. The structure given below is ananalogue of amprenavir; on the structure below please circle and name eachof the functional groups present.

(3 marks

(b)!androlone is an anabolic steroid sometimes taken b" athletes to buildmuscle mass; on the structure below label the indicated atoms as #o$ %o$ 3oor&o.

(% marks

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(c) 'raw the skeletal structures of the following molecules(i) %)bromopropane

(ii) etho*ide ion

(iii) 3)amino)%)meth"lpropanoic acid

(iv) %$&)diaminotoluene

(& marks(d) +lease name the following structures.

Answer!!!!!!

Answer (% marks

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Question " [1" marks](a) ,ighting along the -%)-3 bond of %)chloropentane$ there are fourpossible !ewman conformations. +lease draw the most and the least stableand e*plain "our choice.

Steric hindrance

(3 marks

(b) or each of the substituted c"clohe*ane/s below$ please draw its ring)0ipisomer$ circle the most stable conformation and indicate if the structure is a

cis or transisomer.

Isomer111111111111111111111111111111111111111

Isomer111111111111111111111111111111111111111

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(& marks(c) 2ank the following alkenes in order of increasing reactivit"; from leastreactive (# to most reactive (&. +lace the number corresponding to thecompounds rank below the compound.

(% marks

(d)n the structures provided below$ please draw the arrows showing thecomplete stepwise mechanism for this reaction.

(3 marks

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Question # [1" marks](a) +lease draw the mechanism (including an" relevant resonancestructures to show the formation of the ma4or product for the reaction of thefollowing diene with h"drobromic acid in ether.

(b)5abel the following pairs of compounds as either; constitutional isomers$enantiomers$ diastereomers$ meso or none of the above.

.

(3 marks

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(c) 6sing an" combination of the following reagents$ to show how "ou woulds"nthesise thefollowing products from ben7ene b" 8lling in the blank s9uares with both thereagents and an" intermediates as indicated. Assume that "ou can separateorthoandparaisomers as necessar".

(a:n&$ H3F

(3 marks

(b)-hlorambucil is a s"nthetic drug mainl" used in the treatment of chronicl"mphoc"tic leukemia. It has onl" one p:a under ph"siological conditions.Ehat is the degree of ioni7ation of -hlorambucil at pH >.B$ if its p$ais B.K

D K3.3>L

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(% marks

(c)5abel the diagram of the peptide shown below to identif")

(i each amide bond

(ii each primar" h"dro*"l group

(iii each ester

(iv each chiral carbon

(& marks

(d)There are three isomeric forms of tartaric acid (molecular formula H%-)-HH)-HH)-%H. Erite ischer pro4ections for each of these three forms inthe space below. Also indicate on "our diagram which two of these areenantiomers$ and which is a meso compound. M3N

(& marks

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(e) +hosphoric acid (see the structural formula below is an e*ample of atriprotic acid$ with

p$a# D %.#%$ p$a%D F.%# and p$a3D #%.>F.

(i @*plain what is meant b" a triprotic acid.

Three protons can be lost

(ii ,ketch below the form of the titration curve (i.e. pH against volume of

base added "ou might e*pect to obtain in a titration of phosphoric acid with!aH. Indicate clearl" on "our diagram where the pH coincides with thethree p:avalues of phosphoric acid.

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(3 marks

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3.is 4a5e ma6 be removed

Su440ementar6 7ata

8u9ersAcetic Acid p$a D &.F>+"ridine p$a D B.%3H@+@, p$a D F.>>+henol p$a D J.KJ1 N:R c.emica0 s.i&t data

;R s4ectra0 data

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Chemistry 101 Practice EXAM ANSWERS

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