Question

2-methylocta-4,6-dien-1-amine

Assignment 1: Draw your molecule from IUPAC name

 Using the given IUPAC name, draw your molecule

 Complete the cover page (p.1) of your portfolio with the following:

o Structural formula of the molecule

o IUPAC name

 Use a thin, clear binder or report cover to protect the portfolio

 Submit the following in the binder:

o Cover page as described above (page 1)

Assignment 2: Formula, Molar Mass and Functional Groups

 On a page titled Expanded Structural Formula draw the expanded structure of the

molecule.

o Show every atom and every covalent bond in the molecule

o For every nonmetal atom, add electron pairs as needed so that the atom has eight

valence electrons

 On a page titled Molar Mass Calculation use the expanded structure to determine the

following.

o The molecular formula

o The molar mass (use atomic masses from the periodic table to the hundredths place

for each element)

 On a page titled Functional Groups draw/print the structural formula of your molecule

(expanded or condensed) and indicate the functional groups present by highlighting,

circling, or color-coding each and labeling the group.

Assignment 3: Chiral Carbons and Stereoisomers

 On a page titled Chiral Carbons print/draw the expanded structure of your molecule.

o Determine if your molecule contains any chiral carbons. If there are chiral carbons

in your molecule, circle or highlight all of them. If your molecule does not contain

any chiral carbons explain why none of the carbons are chiral.

 One a page titled Stereoisomers print/draw the expanded structure of your molecule.

o Calculate the maximum number of possible stereoisomers of your molecule using

the following formula:

 Maximum number of possible stereoisomers = 2n

(where n= the number of

chiral carbons in your molecule). This calculation does not include E- or Z isomers

for any compounds containing double bonds

o Draw the possible stereoisomers of the molecule.

 Note that E-, Z- isomers of each stereoisomer are also possible and

would not be accounted for by the formula above; draw any E- or Z isomers.

Assignment 4: Hydrogen Bonding, Polarity and Solubility

 On a page titled Hydrogen Bonding with Water print/draw the expanded structure of

your molecule. (If the structure already contains any dashed lines, make them solid (nondashed)

covalent bonds for this assignment so that they are not confused with hydrogen

bonds)

o Illustrate all the locations where your molecule could form hydrogen bonds with

water either as a hydrogen donor or as a target (receiver) of hydrogen bonds from

water. Do this by drawing bent water molecules as necessary and representing

hydrogen bonds between water and the molecule using dashed lines. Be sure it is

clear exactly which atoms on each molecule are involved in the hydrogen bonds.

o If your molecule is not capable of forming hydrogen bonds with water explain why

not.

o One example of how to represent hydrogen bonding is illustrated below. The

molecule is a receiver of hydrogen bonding from water at the oxygen of the

carbonyl group.

 On a page titled Polarity and Solubility Predictions draw/print the structural formula of

your molecule (expanded or condensed)

o Circle or highlight all polar portions of the molecule

o Make predictions whether your molecule will be soluble in water or not and explain

your rational. Note that there may be no correct answer as often solubility must be

tested. Therefore the explanation may be more important the prediction itself.

Assignment 5: Separation Scheme Correction

 On a page titled Incorrect Separation Scheme print the incorrect separation scheme

provided for your molecule on Blackboard. The top of the separation scheme shows what

other compound is mixed with your molecule. Assume for the purposes of this assignment

that both compounds are solid at room temperature. Also assume that both compounds are

soluble in ether, except ionic compounds. The goal of the separation is the isolate each of

the two compounds from the mixture.

o Below the incorrect separation scheme write a discussion of this incorrect scheme

identifying all of the mistakes in the separation scheme. Keep in mind that there

will be more than one mistake in the scheme.

o For each mistake, give a detailed, scientific explanation of why it is incorrect.

 On a page titled Correct Separation Scheme print/draw a correct separation scheme to

isolate your molecule from the provided second molecule. Make sure to indicate the phase

of each chemical in every step (s, l, g, aq) and write the separation technique used in each

step (ie: vacuum filtration). The list below gives the reagents available in the lab. Use any

of the reagents below to isolate the compounds. Remember that the simplest separation

scheme is the best one. Try to avoid unnecessary steps.

 10% aqueous NaOH  H2O

 5% aqueous NaHCO3  H3PO4

 6M HCl  anhydrous Na2SO4

 5% HCl  anhydrous MgSO4

 Diethyl ether (ether)  Saturated NaCl

 CH3OH  Sodium borohydride (NaBH4)

 lithium aluminum hydride (LiAlH4)  NaCl solid

Assignment 6: Mechanism Correction

 On a page titled Incorrect Mechanism print the incorrect mechanism provided for your

molecule on Blackboard. For the mechanism you will focus on the reaction of the portion

of the molecule drawn only (not the R part). The molecule will be drawn with R groups so

that you may ignore other reactive parts of the molecule. In fact, it is essential that the R

groups are ignored even if they may have an effect on the mechanism. This is not why the

mechanism is incorrect. For any corrections, disregard the parts of your molecule

represented by R-groups.

o Below the incorrect mechanism write a discussion of the incorrect

mechanism identifying all of the mistakes in the mechanism. Keep in mind

that there will be more than one mistake in the given mechanism and that

the product given is not necessarily the correct product of the reaction of

your molecule with the given reagent.

o For each mistake, give a detailed, scientific explanation of why it is

incorrect.

 On a page titled Correct Mechanism print/draw a correct mechanism to react your

molecule with the given reagent. Again, disregard any parts of the molecule represented

by R-groups and focus on the given portion of the molecule. Be sure the correct mechanism

arrives at the correct product of the reaction. The incorrect mechanism may or may not

have the correct product

Assignment 5 incorrect scheme:

Assignment 6 incorrect mechanism

Incorrect Separation Scheme NH NaCl distillation fraction 2 fraction 1 Na Cr NH

Answer 1

Solution:

The molecular structure based on given IUPAC name and other details are expressed below,