10th list: Isomery and Organic reactivity

1. Which of the substances are isomers?

(A) b / c / d

(B) a / c / d

(C) b / a

(D) a / c

(E) a / b / d

Answer (B)

a. C3H8O

b. C3H6O

c. C3H8O

d. C3H8O

2. Below there are two organic compounds and their molecular formula is C3H8. Which is

the isomery that happens between them?

(A) position

(B) function

(C) chain

(D) tautomerism

(E) optical

Answer(A): The first thing is to identify that hydroxyl is in different positions for each

specie. So, if the formula is the same, the organic function is the same, just can be

position isomerism.

3. What or which of the following substances below has geometric isomery?

(A) I, IV

(B) I, III

(C) II, IV

(D) I, II, III

(E) III, IV

(E) Let’s look to the structure of each molecule

What makes a molecule have geometric isomerism? We don’t have any cyclic

compounds, so what we need is the presence of a double bond between carbons and

each carbon in the double must have different ligands, right?

So, let’s see which compounds have what we need!

Just III and IV!! NOTE THAT THE QUESTION DOES NOT SPECIFY THE TYPE OF

GEOMETRIC ISOMERISM (CIS OR TRANS)

4. For compounds are given below! Identify them as cis or trans in order: a, b, c and d

Analyzing this chain, we can classify it into:

(A) trans, cis, cis, trans

(B) trans, cis, trans, trans

(C) trans, cis, cis, cis

(D) cis, trans, trans, cis

(E) cis, trans, cis, trans

Answer (A): Let’s first identify the hydrogens in the double bond.

Now, identify the carbon ligands that make the double bond and realize if they are cis

(same side) or trans (opposite side)

5. In order for the structure below to indicate a compound that has optical activity, we must

replace the R and R’ groups by:

(A) Methyl, ethyl

(B) Ethyl, propyl

(C) hydroxyl, methyl

(D) methyl, methyl

 (E) methyl, hydrogen

Answer (B): To be active, the carbon must be chiral, this means this carbon must be

linked/bonded with 4 different groups, hence ethyl and propyl.

6. Four organic compounds can be found in nature. What/Which is/are the acid(s) that

has/have optical isomers?

(A) I, II

(B) III

(C) II, IV

(D) IV

(E) II

Answer (E) What a carbon must have to present optical isomerism? FOUR DIFFERENT

LIGANDS!!! So, let’s search for it. Only the acid II has 4 different ligands in the carbon,

hence is a chiral carbon, so has optical isomerism

 7. The amphetamine molecule has optical isomerism. What is the carbon’s number that

represent the motivation for this optical isomerism behavior?

(A) 1

(B) 3

(C) 5

(D) 6

(E) 8

Answer (E) For optical isomerism, the molecule must have a chiral carbon, that means

this carbon must be linked/bonded with 4 different ligands. The only one carbon that has

this property in the amphetamine molecule is the carbon number 8

 8. In the saponification reaction CH3COOCH2CH2CH3 + NaOH  X + Y, the products are:

(A) Ethyl alcohol and sodium propionate

(B) Acetic acid and sodium propoxide

(C) Sodium acetate and propyl alcohol

(D) Sodium ethoxide and propanoic acid

(E) Acetic acid and propyl alcohol

Answer: (C) Looking to the organic compound

Remembering the esterification reaction, we know that the ester comes from the addition

of an acid and an alcohol. In saponification, the part that comes from the alcohol

becomes alcohol again and the part that comes from the acid becomes SALT.

Applying this to propyl ethanate we have to:

Look that the only alternative that there is a SALT is letter C and D, but the green part

turns into the alcohol, so this is the propyl alcohol.

9. A given compound was found in nature and has a double bond between two carbons

and it’s an alkene. After some experiments, the researcher realized that just
 transforming this double bond in a simple bond that the properties of this compound

should be applied in humans. What is the organic reaction that the research can do?

(A) Substitution

(B) Addition

(C) Nitration

(D) Sulphonation

(E) Reductive

Answer (B): A double bond for alkene just can be transformed (among the

alternatives given) by addition.

10. The following reaction is given

Which type is this reaction?

(A) Elimination

(B) Addition

(C) Nitration

(D) Sulphonation

(E) Reductive

(A) When a simple bond becomes a double bond this can occur by elimination reactions.