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Org Chem Test

1. An orange or red-brown precipitate is observed when aldehydes react with hydrocyanic acid in a nucleophilic addition reaction. The reaction forms a cyanohydrin. 2. Glycerol is identified as propan-1,2,3-triol. Soap is identified as a sodium salt of a long chain carboxylic acid. 3. Two structural isomers of an organic compound are identified. A racemic mixture is explained as an equal mixture of optical isomers that form due to planar attack from either side being equally likely.

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33 views4 pages

Org Chem Test

1. An orange or red-brown precipitate is observed when aldehydes react with hydrocyanic acid in a nucleophilic addition reaction. The reaction forms a cyanohydrin. 2. Glycerol is identified as propan-1,2,3-triol. Soap is identified as a sodium salt of a long chain carboxylic acid. 3. Two structural isomers of an organic compound are identified. A racemic mixture is explained as an equal mixture of optical isomers that form due to planar attack from either side being equally likely.

Uploaded by

Karen Julao
Copyright
© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
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Download as DOC, PDF, TXT or read online on Scribd
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4.4, 4.

5 TEST MS
1.

(a)

Observation

orange or red-brown precipitate (1)

Structure
CO O H

(b)

or

C O O

(N a + )

(1 )

RCHO + HCN RCH(OH)CN (1)

Equation

Type of reaction nucleophilic addition (1)


Mechanism

(1 )

:C N

(1 )

O :

C N

(1 )
(c)

Type of isomerism

optical (1)

Structural feature

atom with 4 different substituents


or asymmetric or chiral (1)

Isomer 1

Isomer 2

te tra h e d ra l (1 )
m ir ro r im a g e s (1 )

C O O H
C
H

CO O H
C

C H

O H

H O

Method of distinguishing

CH

opposite rotation of polaroid light (1)


[12]

2.

(a)

propyl methanoate;

HCOOC3H7 + OH HCOO + C3H7OH


OR
HCOOC3H7 + NaOH HCOONa + C3H7OH;

(b)

(i)
CH 2O H
CH O H
CH 2O H
propan(e)-1,2,3-triol
OR
1,2,3-propan(e)triol
OR
Glycerol;
(ii)

CH3(CH2)16COONa or C17H35COONa or C18H35O2Na;


(ignore 3 in front of formula but not if indicating
trimer)
(not just anion and penalise Na shown as covalently bonded) soap allow with detergent but not detergent alone;
[6]

CH
3.

(a)

C H 2C H

Structure of P:

H
Structures of Q and R:
CH 3
CH 3
C
C
CH 2CH
H

(1)

C H

C H

C H

and

C
C H (C H 3)2

N O T C 3H
(1 )

(1 )

Q and R in any order

(b)

(i)

Racemic mixture: equal mixture of optical isomers / enantiomers


OR in explanation

Explanation: planar ( >C=O) (1)


attack from either side is equally likely (1)
(ii)

Reagent S: HCN or (KCN / HCl or H2SO4) (1)


O H
Compound T: C H 3 C H

C
C N

C H

Compound U:

C
H

C H

CH

(1)

(1)

C
CN

[9]

4.

(a)

graphical structure for CH3CH2COOH (1)


allow CH3CH2 or C2H5

(b)

(i)

ethanol / CH3CH2OH / C2H5OH not just alcohol (1)


(concentrated or dilute) sulphuric acid / HCl / strong acid / H
not just acid solution

heat / reflux / warm / temperature < 100 C (1)


allow second and third marks if alcohol given
third mark is dependent on first and second marks
second mark is independent on first mark
(ii)

ethyl propanoate (1)

(iii)

CH3CH2COOH + CH3CH2OH CH3CH2COOCH2CH3 + H2O


C3H6O2 + C2H6O C5H10O2 + H2O (minimum for mark) (1)
CH3CH2COOCH2CH3 or C2H5CO2C2H5 (1)

(c)

(i)

compounds with the same molecular formula /


same numbers of same atoms (1)
but different structural formulae / structures or (1)
atoms joined / bonded / linked in different orders / C skeletons
not atoms arranged differently

(ii)

sodium ethanoate / CH3COONa (1)


propan-1-ol / CH3CH2CH2OH / propanol / propan-2-ol (1)
[11]

5.

(a)
(1 )
(1 )
(C H 3 )2 C

B r

C H C H 2C H

(C H 3 ) 2 C

C H 2 C H 2C H

(1 )

:B r

(1)

Br

2bromo2methylpentane (1)
tertiary carbonium ion more stable than secondary (1)
(b)

geometrical or cistrans isomerisation (1)


hex3ene or hex2ene (1)
R

R
C

R
(1 )

C
(c is )

H
C

C
(tra n s )

(C H 3) 2 C

(1 )

C H 2C H 2C H
(1 )

(c)

optical (1)

3methylpent1ene (1)

H
H 3C

H
C H
C H 2C H
(1 )

C H
3

H 2C

CH
H 3C C H

CH

(1 )
[15]

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