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Tutorial 8

Part I - Multiple choice questions

1. Which of the following is called an acyl group?
B. R-CO2. Which of the following used as a suffix of carbaldehyde in naming?

D. all of these
3. When two molecules of acetaldehyde combine to yield the hydroxyaldehyde, the product is known
as _________.
C. Aldol
4. Aryl ketones are prepared by the following reaction. This reaction is called_________________.

B. Friedel-Crafts Acylation
5. Which of the following is an example of an enamine?
C. R2 C = C R NR2
6. Aldehydes and ketones are reduced by NaBH4 or LiAlH4 to yield ___________ and _________
A.10 (primary) and 20 (secondary)
7. Which of the following has the highest boiling point?
8. Which of the following is the most acidic?

9. Which of the following reagents is used for the following conversion?

KMnO4, H2O, heat

10. Alpha- bromination of carboxylic acid by a mixture of Br 2 and PBr3 is called _____________ .
Hell-Volhard Zelinskii (HVZ) reaction
11. Which of the following is an example of diazonium ion?
B. CH3N2+
12. The reaction of carboxylic derivatives by an organometallic reagent to yield an alcohol is called
C. Grignard reaction
13. Lactones are common names for:
C. cyclic esters
14. Which of the following carboxylic acids is not classified as dicarboxylic acid?
C. salicylic acid
15. Which of the following is not considered to be a carboxylic acid derivative?
D. alkylhalide
PART II Namenclature
a) Write the correct IUPAC names.

A. 2-methyl-2-cyclohexanone
D. m-hydroxybenzoic acid

B. N,N- diethylbenzamide
E. N-ethylpropanamide

C. 3-methylpentanenitrile

b) Write the correct structures .



1,4- butanedioic acid




What major product(s) would you expect from the following reactions?

acetic anhydride

What is the best procedure for preparing the following compound? (Requires more than one step)




d) An experiment was done by shaking a ketone containing at least one methyl group or any aldehyde
with a saturated solution of sodium hydrogen sulphite in water.
(i) Predict what will be seen if a reaction occurred?

A white crystalline precipitate

(ii) Write the equation for the reaction between propanone and sodium hydrogen sulphite showing
the essential structure of the product.

(ii) Manipulate this reaction so that it can be used during the purification of an aldehyde.

Shake the impure aldehyde with sodium hydrogen sulphite solution to produce the crystals.
Filter and wash the crystals, and then add a dilute acid or alkali to regenerate the aldehyde.

e) Study the starting materials displayed in the following table and complete it by distinguishing the
structures of the intermediate and final organic product(s) as required.

The intermediate product in the following table is formed when the starting material is treated with
Reagent 1 and the final product is formed when the intermediate product is treated with reagent 2.
Starting material

PART V- Road map

Intermediate product
Reagent 1: NaBH4 then H2O

Final product
Reagent 2: conc. H2SO4

Reagent 1: CH3MgBr

Reagent 2: CH3I

Identify the structures for compounds A, B, C, D, and E

A. CH3 CH2 Cl / AlCl3 , B. KMnO4 , H2O /heat ,

C. SOCl2 ,

D. CH3OH /pyridine ,

E. NH3

PART VI- Concept Understanding

a) Explain the differences between saturated and unsaturated carbon compounds.

b) Explain why alkenes tend to react with electrophiles.

The C=C bond has a high electron density to which electron seeking species are attracted.

c) Find the mechanisms for the following reactions:

I. Ethene with bromine

II. But-2-ene with hydrogen bromide

III. Ethene with concentrated sulphuric acid

d) Justify how bromine can behave as an electrophile.

The electrons in the Br-Br bond are distorted by the electron density on the C=C bond which
induce a temporary dipole on the Br-Br bond.

e) List the advantages and disadvantages of producing ethanol via fermentation process and via
hydration of ethene.

f) Study the following reaction and use the curly arrows to propose a mechanism for it.