Combo of Homework/Review assignments: Organic Chemistry I - Final Exam Study Guide"

Name the following compound:

3 bromo, 6 cyclooctamine

How many σ-bond and π-bond are present in acetylene (C2H2) molecule?

3 sigma; 2 pi bonds

Name the following compound:

3, 7 Diethene-2-octanoll

Name the following compound:

3, Bromo 6, cyclopropane 2, hexanone

The carbonyl carbon in acetic acid contains______ % s-character whereas the carbon in methanol contains ______ % s-character.

33.3%, 25%

Name the following compound:

4-Bromo-6-Chloro cycloctamine

How many σ-bond and π-bond are present in ethylene (C2H4) molecule?

5 sigma; 1 pi bond

Name the following compound:

6 Bromo, N Hydroxy, 4 oxo, 9 Aminohexanoic Acid

Name the following compound:

6 methane, 2 octyn, 1 nitrile

What is electronegativity?

A measure of how strongly the atoms attract electrons in a bond. The bigger the elctronegativity difference the more polar the bond

Describe with suitable diagram the hybridization of carbon in methane

As seen in methane (CH4), carbon can form 4 bonds. The rationale behind this phenomenon is hybridization. Supporting evidence shows that 1 s and 3 p orbitals are being combined to form hybrid orbitals, allowing polyatomic molecule to have 25% s character and 75% p character. Thus, we call methane a sp3-hybridized molecule.

NH3 is a polar molecule but BF3 is non-polar—justify.

Because F is evenly distributed around B but H is not evenly distributed around N

The IUPAC name of Cyclobutyl bromide is _______

Bromocyclobutane

The compound CH3—CH2—CH2—CH3 is the structure of what?

Butane

Write the structure of Oxirane

C 2H 4O Ethylene oxide

Write the structures of benzophenone

C13H10O

Write the structures of acetone

C3H6O

Write the structure cyclobutanol.

C4H8O

Write the structure of Oxolane

C4H8O Tetrahydrofuran

Write the structures of valeric acid.

C5H10O2

Write the structure of Hex-3-yne.

C6H10

Write the structure of Cyclohexane.

C6H12

Write the structure of hexanal.

C6H12O

Write the structure of Iodobenzene

C6H5I

Write the structures of benzaldehyde

C7H6O

Write the structure of ortho-Xylene.

C8H10

Write the structures of meta-Xylene.

C8H10

Write the structures of para-Xylene.

C8H10

Write the structures of vanillin

C8H8O3

Write the structure of n-Hexane

CH3(CH2)4CH3

Why is chloroform (CHCl3) polar whereas carbon tetrachloride (CCl4) is non-polar?

Carbon tetrachloride doesnt have a dipole moment but chloroform has a H and so the electrons will be focused on the Cl, not the H.

The IUPAC name of methyl chloride is _______

Chloromethane

Name the following compound:

Cyclopropoxybutane

Write the structure of Oxetane

C₃H₆O

Write the structure of 2-bromobutanoic acid.

C₄H₇BrO₂

Write the structure of neopentyl alcohol.

C₅H₁₂O or (H₃C-)₃C-CH₂OH

Write the structures of acetophenone

C₆H₅C(O)CH₃

The common name of Methoxymethane is _______

Dimethyl ether

Write the name and structure of a secondary amine.

Dimethylamine

What do you mean by dipole moment? Explain, considering water molecule as an example.

Dipole moment a measure of polarity of a molecule due to the difference of charge on either end of the molecule. Example> H2O has a permanent dipole moment due to H being much less electronegative than O creating a partial negative charge on the O's and a partial + on H's.

What makes resonance structure have decreased stability?

Electron delocalization, an increased amount of potential energy or resonance

The IUPAC name of Cyclohexyl fluoride is _______

Fluorocyclohexane

The IUPAC name of anisole is __________

Methoxybenzene

Name the following compound:

Methoxycyclopropane

Write the name of an ester which is widely used as a solvent in organic chemistry.

Methyl butanoate (fruity pineapple odor).

Name the following compound:

N-Methyl-N-Propyl-butamide

Name the following compound:

N-Methyl-N-Propylbutanal

Name the following compound:

N-methyl-N-ethylpropane

Explain the terms "resonance contributor" and "resonance hybrid" considering benzene as an example.

RC: diff. structures of same molecule each representing a different form that a molecule can take RH: a dipiction of a molecule showing an intermediate form of all the RC in one model Benzene can have 2 different configurations of 3 double bonds and Benzenes res. hybrid would be drawn with 6 dotted lines representing possible double bonds.

Isopropyl fluoride is a _______ alkyl halide.

Secondary

Carbon is ___________ hybridized in acetylene.

Sp

In benzene, the carbons are ___________ hybridized.

Sp2

In carbonyl compounds the carbonyl carbon is ________ hybridized.

Sp2

The state of hybridization of carbon in ethylene is ___________.

Sp2

The carbonyl carbon in acetic acid is ______ hybridized whereas the carbon in methanol is______.

Sp2, Sp3

Describe with suitable diagram the hybridization of carbon in ethylene

Sp2: Unlike methane, ethylene is shaped differently, despite the fact that the carbon in ethylene has the same electron configuration. What accounts for this difference? Supporting evidence shows that the carbon in an ethylene molecule is sp2 hybridized. This means that 1 s orbital is being mixed with 2 p orbitals.

Carbon is ___________ hybridized in ethane.

Sp3

The state of hybridization of carbon in methane is ___________.

Sp3

Describe with suitable diagram the hybridization of carbon in acetylene.

Sp: Supporting evidence shows that acetylene is an sp molecule. This means that 1 s orbital is being mixed with 1 p orbital

tButyl iodide is a ___________ alkyl halide.

Tertiary

Write the structure of Oxane

Tetrahydropyran

Write the structures of maleic acid and fumaric acid. What is their relation to each other?

They are both cis-trans isomers with maleic is the (cis) and fumaric is the (trans), unsaturated dicarboxylic acids. Although these two acids have the same structural formula and differ only in the three-dimensional geometry of their molecules, their properties are very different.

Write the name and structure of a tertiary amine.

Trimethylamine

The ester ethyl methanoate is present in ______

Used in raspberries artificial flavorings and smells like rum

The common name of ethanoic acid is ______

acetic acid

Triethylamine is widely used as an organic _________ in laboratory.

base

Phenol is also known as ___________ acid.

carbolic acid

β-lactam is a four-membered ______ amide whereas ______ lactam is ______ membered cyclic ______

cyclic , gamma, 5, amide

The reverse reaction of esterification is known as ester______

ester"hydrolisis"

As the number of nearly equivalent resonance contributors ___________, the resonance energy ___________

increases, increases

Write the name and structure of primary amine.

methylamine

Higher the electronegativity difference between two bonded atoms, more ___________ is the covalent bond.

polar

Glycerol is an example of _________ alcohol.

polyhydric ("polyol") alcohol

Ethyl bromide is a _______ alkyl _______.

primary, halide

What is rapid pyramidal inversion

rapid pyramidal inversion of the amine nitrogen prevents isolation of the enantiomers except where the nitrogen is part of a ring or has other geometrical constraint. switching between a pair enantiomers

What do you mean by (i) σ-bond and (ii) π-bond? Explain.

sigma bonds are two orbitals overlaping head on and pi bonds are the lobes overlapping

What is hybridization?

the idea that atomic orbitals fuse to form newly hybridized orbitals, which in turn, influences molecular geometry and bonding properties

Write the structure of Imidazole

(C3H4N2)

Write the structure of Pyrimidine

(C4H4N2)

Write the structure of Pyrrole

(C4H5N)

Write the structure of TBME.. "Tert-butyl methyl ether"

(C5H12O)

Write the structure of Pyridine

(C5H5N)

Write the structure of Aniline

(C6H5NH2)

Write the structure of p-Anisidine

(C7H9NO)

Write the structure of Indole

(C8H7N)

Write the structure of Quinoline

(C9H7N)

Write the structure of hexanol.

(CH₃(CH₂)₅OH)

In case of covalent non-polar bond the difference in electronegativity between two bonded atoms is what?

0.0 ≤non-polar covalent≤ 0.5

In case of covalent polar bond the difference in electronegativity between two bonded atoms is what?

0.5< covalent polar < 1.67

Name the following compound:

1 Amino, 5 Methylheptyne

Write the name and structure of two "symmetrical" ethers.

1. Dimethyl ether C2H6O IPUAC = "methoxymethane" 2. Diethyl ether (C2H5)2O IPUAC = "Ethoxyethane"

3 reasons atoms bond?

1. each atom wants a full outermost energy level 2. gain, lose, & share valence electrons to achieve the duet or octet rule "being happy" 3. Gives each atom an electron configuration similar to that of a noble gas

If the electronegativity difference between two bonded atoms is higher than ___________, the bond is called ionic bond.

1.67< ionic

Write the name and structure of two "non-symmetrical" ethers.

1.Ethyl methyl ether C3H8O IUPAC = Methoxyethane 2. cyclopropyl methyl ether C4H8O IUPAC = Methoxycyclopropane

Name the following compound:

2 amino, 3 chloro cyclohexanone

Name the following compound:

2 methylpropyl, 2 amine