Chemistry 30A

Organic Chemistry I
Hung V. Pham
Spring 2016

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Syllabus
Chemistry 30A Syllabus - Spring 2016
Organic Chemistry I Structure and Reactivity
Instructor: Dr. Hung V. Pham

Office: Young Hall 4222A

E-mail: phamhv@chem.ucla.edu
Office Hours: M 2:30-3:30p; W 1:30-2:30p; by appointment, through email or in person

Lecture Times

Lecture 1: MWF 11:00-11:50am in CS 24

Lecture 2: MWF 12:00-12:50pm in CS 24

Course Materials
-

Organic Chemistry (Brown, Iverson, Anslyn, and Foote; 7th edition) and Study Guide (REQUIRED)
ISBN (textbook): 9781133952848; ISBN (study guide): 9781285052618
Any molecular model kit; one option: HGS Molecular Structure Model (STRONGLY RECOMMENDED);
ISBN: 9780716748229

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Syllabus
TAs and Discussion Sections
Section

Day

Time

Location

TA

1A

Tuesday

9:00

Boelter 5436

Song

1B

Tuesday

12:00

Broad 2100A

Cyndi

1C

Tuesday

2:00

Pub Aff 2242

Cyndi

1D

Wednesday

8:00

Boelter 4283

Juno

1E

Wednesday

12:00

Broad 2100A

Cyndi

1F

Thursday

8:00

PAB 2434

Peiyuan

1G

Thursday

9:00

PAB 2434

Song

1H

Thursday

12:00

Boelter 5419

Song

1I

Friday

1:00

Humanits A26

Rob

2A

Monday

2:00

MS 5225

Mike

2B

Monday

3:00

WGYoung 1044

Mike

2D

Tuesday

9:00

Boelter 5420

Mike

2E

Tuesday

1:00

Bunche 3164

Juno

2G

Wednesday

9:00

Boelter 9436

Juno

2H

Wednesday

1:00

Rolfe 3116

Peiyuan

2J

Thursday

1:00

Boelter 5419

Peiyuan

2K

Friday

9:00

Boelter 5419

Rob

2L

Friday

2:00

Lakretz 120

Rob

Cyndi He

Mike Nechay

Rob Thompson

Juno Van
Valkenburgh

Song Yang

Peiyuan Yu

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Syllabus
Grading
Assessment

Points

Exam 1

100

25%

Exam 2

100

25%

BACON Exercises

20

5%

Final Exam

180

45%

Total

400

100%

Grade Standards:

A+ 99.0%

99.0% > A 94.0%

94.0% > A- 90.0%

90.0% > B+ 86.0%

86.0% > B 83.0%

83.0% > B- 79.0%

79.0% > C+ 75.0%

75.0% > C 71.0%

71.0% > C- 66.0%

66.0% > D+ 60.0%

60.0% > D 54.0%

54.0% > D- 45.0%

Missed Exams
Regrade Policy

Academic Integrity

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How do I access BACON?

Visit learnbacon.com
Click Sign Up to create your account.
Follow the instructions and then register for the
appropriate course.
When prompted enter your own student ID # and this PIN:
UCLA$30A$1 Lecture 1 (11am)
UCLA$30A$2 Lecture 2 (12pm)

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Then what?
When each tutorial becomes available throughout the term, you
will receive an email notification (after you have created your
account).
The first tutorial will be available on April 15.
You will receive email reminders if you have not completed a
tutorial before its deadline.
After a tutorial deadline passes (and everyone has completed the
quiz), you will be able to access the content of the tutorial again.
Software issues / questions:
support@learnbacon.com

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Syllabus
Q&A On CCLE
You can ask questions during TA and instructor office hours, and also during discussions and even during
class! But if thats not enough time to ask all of your questions, try posting a question on CCLE (or check if someone
else has already gotten an answer to the same question). Simply log in, click on the Q&A tab on the left, and submit
your question in the correct forum (either chemistry or non-chemistry related). We will post an answer within 48
hours (or we will reply to you individually). Note that the question will be invisible until its been answered. We
encourage you to sign your name when you ask the question (but dont feel obligated to, if you prefer to be
anonymous). Please keep in mind that not all questions are easily answered online. If the answer to your question
requires more in-depth explanation or drawings, it would be better to ask your question in person during office hours
or discussion.

Study Advice
Chemistry is not a spectator sportreading the book and watching the professor work out problems will
likely not be sufficient. Learn how to do problems by working them yourself (without looking at the solutions)
continuously and never falling behind.
Additionally,
- Read the appropriate chapter sections and work on problems as we cover them in lecture.
- Do not wait until the last minute to practice problems.
- Skim the chapter before we cover it in lecture.
- If you have difficulty with a problem, try rereading the appropriate section(s) or your lecture notes and/or the
book, looking at worked-out problems of the same type, etc. If you get totally frustrated with a problem,
dont get hung up on itgo on to something else for a while.
- Use your available resources! This includes (but is not limited to) discussion sections, office hours, and Q&A.
Study strategies that students have found useful in the past include study groups, flashcards, working questions
from old tests and quizzes, reworking assigned problems and examples, and reviewing their tests before the final
exam. Most importantly, dont give up!

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Chapter 1

Covalent
Bonding &
Shapes of
Molecules

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What is Organic Chemistry?

Study of matter
Structure Properties Reactions

Chemistry

Organic

The

vs. Inorganic?

study of the compounds of carbon

Glucose

Adenine

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Schematic View of an Atom

A small dense nucleus,
diameter 10-14 - 10-15 m,
which contains positively
charged protons and
most of the mass of the
atom
An extranuclear space,
diameter 10-10 m, which
contains negatively
charged electrons

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Electron Configuration of Atoms

Aufbau

Principle:

Orbitals fill in order of increasing energy from lowest

energy to highest energy
Pauli

Exclusion Principle:

Only two electrons, with opposite spins, can occupy

an orbital
Hunds

Rule:

When orbitals of equal energy are available but there

are not enough electrons to fill all of them, one
electron is added to each orbital before a second
electron is added to any one of them

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Electron Configuration of Atoms

Table

1.3 The Ground-State Electron

Configuration of Elements 1-18

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Lewis Dot Structures

Valence

shell:

the outermost occupied electron shell of an atom

Valence

electrons:

electrons in the valence shell of an atom; these

electrons are used to form chemical bonds and in
chemical reactions
Lewis

dot structure:

the symbol of an element represents the nucleus and

all inner shell electrons
dots represent valence electrons

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Lewis Model of Bonding

Atoms

bond together so that each atom acquires

an electron configuration the same as that of the
noble gas nearest it in atomic number
an atom that gains electrons becomes an anion
an atom that loses electrons becomes a cation
the attraction of anions and cations leads to the
formation of ionic solids
an atom may share electrons with one or more atoms
to complete its valence shell; a chemical bond formed
by sharing electrons is called a covalent bond
bonds may be partially ionic or partially covalent;
these bonds are called polar covalent bonds
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Electronegativity
Electronegativity

a measure of an atoms attraction for the electrons it

shares with another atom in a chemical bond
Pauling

scale

generally increases left to right in a row (period)

generally increases bottom to top in a column (group)

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Types of Bonds
We

divide bonds into

Ionic bonds
Nonpolar covalent bonds
Polar covalent bonds
Although

all covalent bonds involve sharing of

electrons, they differ widely in the degree of
sharing
Difference in
Electronegativity
Between Bonded Atoms
Less than 0.5
0.5 to 1.9
Greater than 1.9

Type of Bond
Nonpolar covalent
Polar covalent
Ions form

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Polar Covalent Bonds

An example of a polar covalent bond is that of H-Cl
The difference in electronegativity between Cl and H is
3.0 - 2.1 = 0.9
We show polarity by using the symbols d+ and d-, or by
using an arrow with the arrowhead pointing toward the
negative end and a plus sign on the tail of the arrow at
the positive end

d+ dH Cl

d+ dH Cl

Cl

Cl

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Lewis Structures
To

draw a Lewis structure:

1. Determine the number of valence electrons

2. Determine the arrangement of atoms
3. Connect the atoms by single bonds
4. Arrange the remaining electrons so that each atom
has a complete valence shell
5. Assign formal charges if necessary
**Watch for exceptions

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Formal Charge
Formal

charge: the charge on an atom in a

molecule or a polyatomic ion

To derive formal charge:

1. Write a correct Lewis structure for the molecule or ion.
2. Assign each atom all its unshared (nonbonding) electrons and one-half
its shared (bonding) electrons.
3. Compare this number with the number of valence electrons in the
neutral, unbonded atom.
Formal
charge

Number of
= valence electrons
in the neutral,
unbonded atom

All
One half of
unshared + all shared
electrons
electrons

4. The charge on a molecule is the sum of all the formal charges on the
atoms.

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Exceptions to the Octet Rule

Molecules containing atoms of Group 3A elements,

particularly boron and aluminum

Boron trifluoride

: Cl

Al
: Cl :

:F:

: Cl :

: :

: :

:F

6 electrons in the
valence shells of boron
and aluminum

:
: F:

Aluminum chloride

Atoms of third-period elements have 3d orbitals and may

expand their valence shells to contain more than 8
electrons
Phosphorus may have up to 10
Sulfur may have 8, 10, or 12

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Functional Groups
Functional

group: an atom or group of atoms

within a molecule that shows a characteristic set
of physical and chemical properties

Functional

groups are important for three

reasons;
1. the units by which we divide organic compounds into
classes
2. the sites of characteristic chemical reactions
3. the basis for naming organic compounds

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Alcohols
Alcohols

contain an -OH (hydroxyl) group

H H

:
-C-O-H

:
Functional
group

H-C-C-O-H
H H
Ethanol
(an alcohol)

Ethanol

may also be written as a condensed

structural formula
CH3 -CH2 -OH

or

CH3 CH2 OH

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Alcohols
There are two alcohols with molecular formula C3H8O
HHH
H-C-C-C-O-H
H HH
H
HOH
H C-C-C-H
HH H

or CH3 CH2 CH2 OH

a 1 alcohol

or

OH
CH3 CHCH3
a 2 alcohol

Constitutional isomers: molecules with the same

molecular formula, but different connectivity
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Amines
Amines

contain an amino group: a nitrogen

bonded to one, two, or three carbon atoms
Similar to alcohols, an amine may by 1, 2, or 3

Methylamine
(a 1 amine)

CH 3 N H
CH 3
Dimethylamine
(a 2 amine)

CH 3 N H

CH 3 N CH 3
CH 3
Trimethylamine
(a 3 amine)

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Aldehydes and Ketones

Aldehydes

and ketones contain a carbonyl (C=O)

group
O

C H
CH3 -C-H
Functional Acetaldehyde
group
(an aldehyde)

C
CH3 -C-CH3
Functional Acetone
group
(a ketone)

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Carboxylic Acids
Carboxylic

acids contain a carboxyl (-COOH)

group
O

:O:

Functional
group

CH3 -C-O-H

C O H

or CH3 COOH or CH3 CO2 H

Acetic acid
(a carboxylic acid)

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Carboxylic Esters
Ester:

a derivative of a carboxylic acid in which

the carboxylic hydrogen is replaced by a carbon
group
CH3 -C-O-CH2 -CH3

Functional
group

: O:

O
C O

Ethyl acetate
(an ester)

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Carboxylic Amides
Amide:

a derivative of a carboxylic acid in which

the -OH of the -COOH group is replaced by an
amine
O
C N
Functional
group

O
CH3 -C-N-H
H
Acetamide
(a 1 amide)

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VSEPR (Valence-Shell Electron-Pair Repulsion)

Based on the concepts that

Atoms are surrounded by regions of electron density
Regions of electron density repel each other

H H
H

H
H

O H C C H H C N

O C

: :

2 regions of e- density
(linear, 180)

3 regions of e- density
(trigonal planar, 120)

4 regions of e- density
(tetrahedral, 109.5)

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