Organic Chemistry: Nomenclature Assignment

Name the following '"1)

H3C- C-CH311o

H3C-0-CH35)

8) CH3- CH2-OH

H3C-C-OH11

12) 0H H

1 IH-C-C-H

1 I15) HO OH

<O>-C1'O O~3 6:~31) 628} 'OH 29) . 30)

H H H Br H H HI I I I I I IH-C- C-C-C- H H-C-C=C-C-HI /I f f I I32) H o H H 33) H H

H3C-CH-C~I

2) OH 3)0 4) 0H3C-CH _c1'O

6) Z 'H

qOH-C'0-CHz-CH

37)

9) H3C-CH2- 0 -CH310) U 11) <D>

H3C-C-CH3 ,.:011 H C-Cr

13) 0 14) 3 'H

CH3IH3C-CHZ-CHZ-C-CHZ-CH3

I34) CH3

C~f .

HzC-CHZ-CH-CHz-CHZI I~C C~

H3C-C=C-CH2ICH3

H3C- C- CHZ- CHZ-OH11o

1'0·CH C=CH'-C

43); 'H

Ci Cl, //C=C,

H CH346)

Cl CH3

'C=C// ,

H Cl

H3C CH3I IHC-CH-CH-CH3I I

35) H3C CH3

CH3IHZC-CH -CH -CH3

I ICH3 CHZ-CH336)

CH3IH3C-C-CHZ-CH

Z-CH

3I38) H3C-CH -CH3

1'0HO- CHr CHr CHrC

40) 'H

1'0H3C-CHz-CHz-C,

42) OH

44)

~oH3C-CHz-C'0_CH

3

37)

H H H H H H HH OH H

I 1 1 I I I 1H-C-C-C-C-H I 1 I I H-C-C-C-H

I I I I H-C-C-C-OH 1 1 1H H CH3H

1 1 1 H CH H16) 17) H H H 18) 3

39)

H H H H H H

<D>--t-OHI' I I I I /,-0

H-C-C-C-H H-C-C-C1 1 1 1 1 'OH 41)

19) H 20) H OH H 21) H H

H H H HI I HZC-CH I I

H-C-C- Br' I 11 H-C-C-C- Br1 1 23) HZC-C- Br

1 11 1

22) H H 24) H 0 H

H H , H H'C/ H H H 1 1 1'0/'" I I / H-C-C-C

H C-C- Br H-C-C=C 1 1 'OHZ I 1 1 -,

25) H 26) H Br H 27)H CH3

50)

H Cl'c::::'c// \.

47) H H

H H"'C=C// '"

HOOC COOH

HZC=C-HI -,

45) 0-CH3

H H\=c// '\

48) H Cl

Organic Problem Solving

1. Suggest a way (either physical or chemical) to distinguish between ethanol andmethoxymethane.

'""""'1=f~j!.

£!-P

tI(}

1'--'L]i.JJrJZ«:Jg

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8. When pentan-Zsol and pentan-S-ol are each heated with an acidified solution ofpotassium permanganate (VII). the colour ofthe solution changes from purple to nearlycolourless.

2. Compound A, of formula C,H,O. is oxidized to compound B of formula C,H,O. B isfurther oxidized to compound C of formula C,H,O,. C reacts with A to produce acompound D of formula C,R,O,. Give the names of structures A, B, C, and D, explainyour reasoning, and write out one of the mechanisms.

a) What is the oxidation stated of the manganese product?b) Name another reagent which would have the same effect upon the a!cohols as

potassium permanganate (VII)c) Draw the structural formulae of the two alcohols and the products of their reactions

with potassium permanganate (VII). (IB exam 1990).

9. The chemical formula C,H,01ias two isomers. Draw each isomer and identity thefunctional group in each case. Predict how the boiling points and solubility in waterwill differ. Explain the basis for your predictions.

10. Predict the reagents (3) necessary to produce the following:a) methylmethanoateb) ethylbutanoatec) propylethanoate

3. A compound offonnula CJR,O exists as two isomers, A and B. With a strong oxidizingagent, A forms a compound C of formula CJR,O, while B forms compound D offormula C,H,O,. D turns blue litmus red. Give names and structures of the fourcompounds, linking compounds that are related.

4. The compounds butanone, l-butanol, ethoxyethane, and butane have boiling points of272 K, 307 K, 352 K and 390 K, though not in that order. Match the compound with theboiling points, explaining your reasoning.

5. Discuss the chemical reagents and reaction conditions necessary to complete each of thethree steps in the reaction sequence shown below.

step I step 2 step 3CH,CH;CH, -------> CH, CH CH, ------> CHJ-C-CH, ------> CH,CHCH,

I II IOH ° OH

6. An aliphatic compound, X, is known to have a molecular formula C,HIOO.a) Compound X reacts with sodium metal to produce hydrogen gas. To what class of

compounds may compound X be assigned? Write 3 possible structural formulae for'compound X.

b) Dehydration of compound X by hot, concentrated sulphuric acid yields a gaseouscompound, Z, of formula C,H,. Write a balanced equation which describes thisprocess. (IB exam 1993)

7. Compound A, CJR,O, is a liquid which reacts with an oxidizing agent such asCr,O, ., and is thereby oxidized to B, CJR,O" a strongly smelling liquid.

Compound' A also reacts with LiAIH, (a strong reducing agent) to form compound C,CJR,o. This is easily dehydrated to give a gas, CJR" which reacts with hydrogenbromide to form D.

The compounds Band C react together in the presence of concentrated R,SO, e'q) to formE, C,HI2O" a liquid with a pleasant, fruity smell.

Write structural formulae and names for the compounds A, B, C, D and E.

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11. Liquid A on standing with silver nitrate solution gives a cream precipitate and a solutionof'B. When B is boiled with concentrated sulphuric acid, it gives a colourless gas C.C reacts with bromine to give a liquid D which 0 boiling with hot, concentrated, a!coholicsodium hydroxide gives a gas E. E reacts with an oxidising agent such as acidified

KMnO/OR", to form ethan-I,2-dioic acid, (aka: oxalic acid). If;l\contains two carbon atoms,identify A to E, explain your reasoning and write equations for all the reactions occun·ing.

12. A solid P bums with a very smoky flame and a solution ofP is very slightly basic. When asolution of P in water is treated with bromine water, a white precipitate, Q, forms. WhenP is treated with concentrated nitric acid a yellow solid, R forms. Identity P, Q, and Randgive equations for the reactions.

13. Show by means of equations and essential reaction conditions only, how you would carry outthe following transformations, (using reactions you have already met):

(a)(b)(c)(d)

H,C;CH,CH,CH,OHC,H,C,H,

into'intointointo

CHJCH,CH,OH(OH)CH,CH, (OH)C,H,CIC,H,COOH

2