All the answers should be written on the exam form.

Answers should be written just in black/blue pen.

No other aids allowed except the periodic table.
Time allotted for the exam is not more than 55 minutes.

NSU-CHEM 2400 - Organic Chemistry 1

Exam 1
Dr. Carmit Alexenberg
October 2021
Name:
1) (18 points)
a. (12 points – 3 points for each structure) For each of the following compounds (1,
2 and 3) show 2 other resonance structures, including any lone pairs and charges.
b. (3 points) For compound #3 write on each of the 3 structures form if it will be the
largest or major or minor contributor.
c. (3 points) For compound #2 draw the resonance hybrid.

+
H3C
O : CH2
:

H2C
Compound #1
CH2

Compound #2
:O:
:

S
CH3
N
:

CH3
Compound #3 largest/major/minor largest/major/minor
largest/major/minor
 Resonance hybrid for
Compound #2

2) (9 points) Show the acid-base reaction between the following molecules (both written
as acids). Show arrow pushing (2 points), write products (2 points), include the pKa
values (2 points), predict equilibrium (1 point), and write under each molecule if
function as acid/base/conjugated acid/conjugated base (2 point).
HINT: One molecule needs to be written as acid and to react with the other molecule
that needs to be written as a base.

SH NH2

H3C CH3

CH3
 3) (14 points) For each of the pairs below, circle the more acidic compound (the indicated
hydrogen - 1 point for each) and determine the effect responsible for such observation
using ARIO methods, or if it is an exception to the rule (1 point for each).

CH3
CH3
NH2 OH
Br A/R/I/O/exception
F F CH3
I

H3C H3C
SH A/R/I/O/exception
OH
H2C H2C
O

CH3
H3C NH2 H A/R/I/O/exception
CH3

O O
H3C H2C CH3 A/R/I/O/exception
CH3
H

H H
A/R/I/O/exception
CH3 H3C

H3C H3C
CH3

F OH F OH
Br H3C A/R/I/O/exception
CH3 F
CH3 Br

SH OH
H3C H3C A/R/I/O/exception
CH3
O
 4) (4 points) Which of the following function as Lewis Acid, but NOT as Brønsted-Lowry
acid?
a. HCl
b. H3O+
c. BCl3
d. H2O

5) (4 points) Which of the following chair conformation represent the most stable
conformations of the FOLLOWING molecule?

Br

CH3
H3C CH3

Br

CH3 CH3 Br
H3C H3C
H3C H3C
H3C Br
Br
H3C
CH3
H3C CH3 CH3
A B C D

6) (4 points) Which of the following is the least stable conformations?

H3C CH3
Cl H3C CH3
Cl

Cl Cl
H3C
H3C

CH3 b c d
a CH3
7) (4 points) What is the IUPAC name of the following compound?
H3C

Br

Br

a. 1,3-dibromo-4-ethylcycloheptane
b. 2,4-dibromo-1-ethylcycloheptane
c. 1,6-dibromo-2-ethylcycloheptane
d. 1,6-dibromo-5-ethylcycloheptane

8) (4 points) What is the IUPAC name of the following compound?

Cl

a. 2-chloro, Bicyclo[5.4.3]octane
b. 6-chloro, Bicyclo[3.2.1]octane
c. 2-chloro, Bicyclo[3.2.1]octane
d. 6-chloro, Bicyclo[5.4.3]hexane

9) Which of the following structures represents a different compound from the other
three?
CH3 CH3 CH3
CH3
H
H
CH3

H3C H H CH3
CH3
H H

b c d
a
10) (4 points) Which of the following Newman projections represents the most stable
conformation of 3-bromopentane (Hint: first draw the molecule)

H Br
H H H H
Br CH3

H H H H Br H CH3
Br
CH3 H CH3 CH3

a b c d

11) (4 points) Which of the following Newman projections represents the most stable
conformation of 1-fluoro-4-methylpentane (Hint: first draw the molecule)
F F
CH2 H CH2
H CH3 H H
H H

H H H H H H
H H
CH2 H CH2
F F
a b c d

12) (3 points) Circle ALL the right statement regarding the following interactions?
a. Anti interactions is lower in energy than Gauche interactions
b. Anti interactions is higher in energy than Gauche interaction
c. Eclipsed conformation is lower in energy than Staggered conformation
d. Eclipsed conformation is higher in energy than Staggered conformation
e. Eclipsed interactions is higher in energy than Gauche interactions
f. Eclipsed interactions is lower in energy than Gauche interaction
13) (10 points) For the molecule below, answer questions a-c:
a. (4 points) What type of functional group is NOT present?
i. Amide
ii. Ester
iii. Ketone
iv. Ether
v. Amine
vi. alcohol

b. (4 points) What is the geometry of carbon #4?

i. Tetrahedral
ii. Trigonal planar
iii. Trigonal pyramidal
iv. Bent

c. (4 points) What is the hybridization of the carbon/nitrogen atoms indicated with

arrows 1, 2, 3 and 4.
i. 1 – sp2, 2 – sp3, 3 – sp, 4 – sp3
ii. 1 – sp, 2 – sp3, 3 – sp3, 4 – sp2
iii. 1 – sp, 2 – sp3, 3 – sp2, 4 – sp2
iv. 1 – sp, 2 – sp2, 3 – sp3, 4 – sp2
3
2
H3C
OH
O
Br
NH Cl
O S
O 4

H3C
Cl

O O
CH3
CH3

1
 14) (8 points) For the molecule below, answer questions a-b:
a. (5 points) Using the indicated letters, identify and circle (on the structure below)
the most acidic hydrogen (A), one vinyl carbon (V), one allylic carbon (L), a t-
butyl GROUP (T), isopropyl GROUP (IP), and an isobutyl GROUP (IB).

b. (3 points) How many Pi-bonds does this molecule have?

a. 5
b. 4
c. 2
d. 3

H3C
H3C CH3
CH3

HC
H3C CH3 NH
CH3
H3C CH3
H3C

CH3

15) (4 points) Which structure(s) contain(s) an oxygen that bears a formal charge of +1, a
neutral nitrogen, and a carbon that bears a formal charge of +1. All lone pairs of
electrons are drown.
+ +
OH
:

OH2 OH2 OH
:

:
:

:
:

– – –
:

H3C CH2 H3C CH2 H3C CH3 H3C CH2

+
: NH2 : NH2 : NH2 NH3

a b c d
Extra credit (5 points):
Draw the gauche conformer of the following compound looking down the indicated bond .