HARAMAYA UNIVERSITY

College of Health and Medical Sciences

Medical Laboratory Sciences Students Year-II, Semester-II

Module name: Chemistry

Module Code: Chem-M2162

Course Title: Organic Chemistry

Miscellaneous questions prepared from Chapters 1-3

Prepared by: Tsegu K. (PhD)

2024 @ CMHS, Haramaya University

Part-I: Multiple choice questions
Q1. Which one of the following is not true about the relationship between the single, double and
triple bonds and the SP3, SP2 and SP hybridized orbitals?

A) Singles bonds have a SP3 hybridized orbital

B) Double bonds have a SP hybridized orbital

C) Triple bonds have a SP hybridized orbital

D) Double bonds have a SP2 hybridized orbital

Q2. The inductive effect of an electron withdrawing group (EWG) on the acidity of a given
molecule depends on the following factors, except one.

A) The type of electron withdrawing group (EWG)

B) The proximity of the EWG to the acidic functional group of the molecule

C) The numbers of the EWG

D) None

Q3. Which one of the following is a polar molecule with a dipole moment value of greater than
zero (µ > 0)?

Q4. Which one of the following compounds is not organic compound?

Q5. Which one of the following functional groups is not a member of the hydrocarbon functional
group?

Q6. Of the following functional groups, which is different from the others?

Q7. Nitrogen containing amino functional groups can be found in different forms based on their
alkyl substituents. Which one of the following groups is a tertiary amine?

Q8. Hydroxyl functional group containing alcohols can be synthesized through interconversion
of different functional groups using various reaction types. Which one of the following reaction
types is not an appropriate reaction to synthesize alcohols?

A) Catalytic hydrogenation reduction of alkenes

B) Hydride reduction of aldehyde or ketone carbonyl groups

C) Hydration of alkenes

D) Hydroxyl substitution of alkyl halides

Q9. All, except one, of the following factors lead to the preference for S N1 over SN2 substitution
reaction

A) Steric effect

B) Effect of conjugation

C) Neighboring group participation or effect of adjacent nucleophic substituents

D) Effect of adjacent carbonyl groups

Q10. Aldehydes and ketones can be synthesized from alcohol starting materials by oxidation
reaction using different oxidizing agents. Which one of the following is not appropriate oxidation
reaction and/or oxidizing reagent to synthesize aldehydes from primary alcohols?

A) PCC oxidizing reagent

B) Swern oxidation reaction

C) Jones oxidizing reagent

D) A & B

Q11. Of the following functional groups, which one is not derived from carboxylic acid
functional group?

Q12. Which one of the following is not a characteristic of SN1 type of substitution reaction?

A) The first rate determining step depends on the concentration of the nucleophile

B) It has two transition states

C) The reaction proceeds through the formation of a tricoordinated carbocation containing

intermediate product

D) The reaction involves only a single or unimolecular species at its first step
Q13. Which one of the following is not a logical combination of nucleophilic substitution
reaction?

A) Cationic electrophile and cationic nucleophile

B) Cationic electrophile and neutral nucleophile

C) Cationic electrophile and anionic nucleophile

D) Neutral electrophile and neutral nucleophile

Part-II. Write-up questions

Q1. Write all the numbers of sigma (σ) and pi (π) bonds of the following chemical structures.

Q2. Write the percentage of the S- character and P-character of the following hybridized
orbitals.

(a) SP3 (b) SP2 (c) SP

Q3. Define cleary the following four quantum numbers of an electron of a given atom.

a) n

b) l

c) ml

d) ms

Q4. Write the values of the four quantum numbers (n, l, ml, and ms) of the fifth electron of 3d5.
Q5. Which one of the molecules in each of the following pair is more acidic and why?

Q6. The following morphine compound has many different functional groups. Indicate all the
functional groups with an asterisk (*) and write their names.
Q7. Amide functional groups can be synthesized directly from carboxylic acid derivatives using
alkyl amines. But, it is difficult to synthesize amides (B) directly from the carboxylic acid (A)
itself as shown in the following reaction. Explain why it is impossible and deduce another
reaction type used to convert carboxylic acid to amide in indirect way.

Q8. Write the appropriate reagents used to synthesize the products from the given starting
materials or reactants shown in each of the following reactions.
Q9. Write the reasonable products which can be synthesized from the corresponding starting
materials and reagents shown in each of the following reactions

Q10. As it is shown in the following reaction, it is not possible to introduce an alkyl group into
the alpha-position of a carboxylic acid by using a strong base like LDA and alkyl halides by
deprotonating the hydrogen atom shown in red. Explain the reason and propose another option
which can solve such problem.
Q11. Esters with different alkyl groups (R) can be synthesized using carboxylic acid and its
derivatives as starting materials. But, if we want to introduce only methyl group into the
carboxylic acid (A) to synthesize methyl ester (B) using the reaction shown below, what
appropriate reagent (C) can we use?

Q12. Propose an appropriate starting material to synthesize the following corresponding products
using the given reagents.
Q13. Write the products of the epoxide ring opening reactions using S N1 or acidic condition (a)
and SN2 or basic condition (b) substitution reactions shown below.

Q14. Elimination reaction

- Definition of elimination reaction

- Types of elimination reactions and their differences

- Types of ß-elimination and their differences

- Write the two products of the following elimination reaction based on the Saytzeff and
Hoffmann rules.

- Write the two products of the following elimination reaction type (Hint: ester is thermally
decomposed to two products which is known as pyrolysis).

-Write the product of the following elimination reaction (Hint: it is a type of Cope elimination
reaction)
Q15. Addition reactions
- Definition of addition reaction

- Types of addition reactions (hydration, hydrohalogenation, dihalogenation)

- Write the product of the following addition reaction according to the Markovnikov’s rule.

- The order of reactivity of halogens toward alkene addition reaction and which one of the
halogen atoms is and/or more preferred? Why?

- Write the product of the following addition reaction (Hint: addition of hypohalous acid to
alkene)

-Write the product of the following reaction (Hint: Michael or conjugate addition reaction)

Q16. Rearrangement reactions

- Definition of rearrangement reaction

- In the following Beckmann rearrangement reaction, why the ethyl group anti to the hydroxyl
group of the oxime is migrated to the electron deficient nitrogen to produce the substituted amide
shown?
- The following pinacol to pinacolone rearrangement reaction provides two ketone products (A
and B). Which one of the two products (A or B) is more stable and why?