CH 117: ORGANIC CHEMISTRY I

Revision and/or Quiz Questions: SET I

1. Organic chemistry is the chemistry of compounds of carbon except for a few inorganic
compounds such as carbonates (CO3-2, HCO3-1, CN-, CO2 and CO. Organic compounds
number in excess of 15 million. Account for the fact that unlike any other element in the
Periodic Table, carbon form millions of compounds.
2. Carbon forms both single and multiple bonds between its atoms and with other elements
through its ability to form different hybrid orbitals such as sp 3, sp2 and sp. Explain how each
of the set of hybrid orbitals is formed.
3. Carefully study the structure of the organic compound below, then answer questions that
follow.

i) What functional groups are present in the compound?

ii) Which atoms (indicate by numbers e.g. 13 & 14 etc ) have:
a) sp3-sp3 bonds? (3)
b) sp3-sp2 bonds? (5)
c) sp3-sp bonds? (1)
d) sp2-sp2 bonds? (2)
e) sp2-s bonds? (1)
f) p-p π-bonds? (3)
g) sp-s bonds? (1)
h) sp3-s bonds? (12)
4. For each of the molecular formulae below, give all possible structural isomers.
a) C6H12
b) C6H14
c) C7H14
d) C7H16
5. Briefly explain the following:
a) Electrophile b) Nucleophile c) Addition reaction d) Substitution reaction
e) Rearrangement reaction f) Elimination reaction.
6. Alkanes are used mainly as fuels and undergoes free radical substitution reactions with
halogens to form alkyl halides but not addition or elimination reactions.
a) Based on bonding principles explain the above chemical behavior of alkanes.
b) Give a detailed reaction mechanism for the free radical substitution reaction between
ethane and bromine under ultra-violet light irradiation. (Assume that the reaction stops at
formation of CH3CH2Br).
7. Organic Nomenclature involves following systematic set of Rules to name compounds. Use
the IUPAC rules to name compounds I to VIII below.

8. Derive structures of compounds A to H below from the given names.

A: 1,2,4-trimethylcyclohex-1-ene
B: 2-propyl-1-heptene
C: 1,4,6-trimethylcyclohex-1-ene
D; 2-isobutyl-1-heptene
E: (E)-6-ethyl-8-methylnon-4-ene
F: (Z)-4,6-diethyl-2-methylnon-4-ene
G: 1,5-dimethylbicyclo[2.2.2]oct-2-ene
H: bicyclo[4.1.0]hept-1(6)-ene
9. Alkenes are very reactive hydrocarbons mostly undergoing addition reactions. Study the
reactions below then answer questions that follow.

a) Name the type of each addition reaction which compound A is undergoing to form B, C,
D, and E.
b) Write a mechanism in each case to account for the formation of the given product.
10. Compound F (C6H12) reacted with Br2 in the presence of benzoyl peroxide while being
irradiated with a UV lamp to give product G (C6H11Br). Treatment of G with alcoholic
NaOH gave 2 isomeric products H and I in 19:1 ratio respectively (C6H10). On treatment with
ozone and dimethyl sulfide, whereas H gave a single product J (5-oxohexanal), I gave two
products K and L. Identify the structures of compounds F to L and explain the chemistry in
each step.

11. The reaction of compound M (shown below) gives 2 isomeric addition reaction products, N
and O. Identify the structures of products N and O and use mechanisms to explain their
formation.

12. Name compounds P to S below, clearly indicating the stereochemistry (E/Z) at all C=C
bonds.

13. In the Scheme below each of the letters T to X stand for either a structure of a compound or a
name of reagent/reaction conditions needed to complete the chemical conversions. Give the
structure or name represented by each letter.
14. Compounds IX and X are subjected to reactions as shown. Identify the products XI, XII,
XIII and XIV.

15. In an Electrophilic Aromatic Substitution (EAS) reaction, an Electrophile, E+ replaces an H+

in an aromatic compound as shown below. For the electrophile to be generated a catalyst is
needed.

In the reactions shown in the scheme below.

a) Identify the Electrophiles in reactions R1 and R2.

b) Show how each electrophile is formed by its interaction with the catalyst.
c) Write the complete mechanism for formation of each product.

16. Compound A, C3H8 was treated with bromine under UV light to form compound B, C 3H7Br.
Reaction of B with dilute NaOH gave product C, C3H8O which on treatment with KMnO 4
gave compound D, C3H6O. On reacting compound C with concentrated H2SO4 a product E,
C3H6 was obtained. Compound E was also formed when B was treated with alcoholic NaOH.
Acid catalyzed reaction of E with compound F, C6H6, resulted into compound G, C9H12.
Reaction of G with oxygen using a catalyst gave phenol and compound D.
a) Write reaction equations for all reactions described above and give structures of
compounds A to G.
b) Write reaction mechanisms for reactions leading to formation of:
i) B from A.
ii) G from E and F.
17. From the compounds named below give their structures including the indicated
stereochemistry where applicable.
1. (E)-3-(but-1-en-1-yl)cyclopentan-1-ol
2. trans-cyclohexane-1,3-diol
3. (2E,5E)-2-methylhepta-2,5-dien-1-ol
4. 5-ethylcyclohex-3-en-1-one
5. (E)-2,6-dimethyl-5-oxohept-2-enenitrile
18. Both 1-propanol and propene undergo acid catalyzed reactions with benzene to form cumene
as shown in the scheme. Write mechanisms which explain this observation.

19. In the scheme shown below, the arrow pushing is not shown. Draw the arrows in all places where
they are needed to complete the transformation.
20. Phenol is a weak acid which reacts with strong bases such as NaOH. The acidity of phenol is
explained by the resonance stability of its phenoxide ion shown below.

Use arrow pushing to show the formation of the different resonance forms of the phenoxide
ion.

21. Write the term or phrase which is described by each of the sentences.
____________________The mathematical constructional on the region of highest probability
of finding an electron around the nucleus.
____________________The various forms of the same compound which are due to
redistribution of electrons on sp2 hybridized orbitals.
_____________________ Molecular structural modification which transform a compound
into its constitutional isomer without changing its elemental composition.
_____________________A term which defines shared properties of a family of organic
compounds.
______________________A reaction of highly electron deficient compounds containing a
good leaving group ortho or para to an electron withdrawing group such as nitro group.
______________________Methyl groups of a tertiary carbocation stabilize it through this
type of electron donation.

22. a) Complete the scheme below by writing the correct structures of the compound or
formula for reagents A to E.

b) Identify each of the 5 reactions as addition, substitution, elimination or rearrangement

23. Study the bonding in the compound below, then, answer questions that follow.

Choose the most correct answer for items I - III

I) The compound has _____________ sp3 hybrid orbitals.
A) 16
B) 12
C) 8
D) 6
II) There are _______________ sp2 – sp2 bonds in this compound.
A) 4
B) 3
C) 2
D) 1
III) Overall the compound has ________________ π-bonds.
A) 3
B) 4
C) 6
D) 8

24. Study the structure of the organic compound below and answer the question
that follow.

Identify the overlapping orbitals, types and number of bonds involved in

each of the bonds 1 – 10