CHM 380

Fall 2013

Homework #1 Due September 12th

Please answer all questions on additional paper

1. For the following acids & bases with the given pKas i) ii) iii) draw the acid and base (protonated and deprotonated) forms and label them use Henderson Hasselbalch to calculate the ratio of the two forms at pH 7.86 calculate the concentration of the base form if the acid form is 0.1 M at pH 7.86. NOTE: The concentration may be extremely large or small. ), pKa = 4.86

A) Propanoic Acid ( a. Acid: Base: a. pH = pKa + log

[CH 3CH 2COO ] [CH 3CH 2COOH ] [CH 3CH 2COO ] [CH 3CH 2COOH ]

7.86 = 4.86 + log

3.00 = log

[CH 3CH 2COO ] [CH 3CH 2COOH ] [CH 3CH 2COO ] [CH 3CH 2COOH ]
[CH 3CH 2COO ] (0.1M )

1.0 x 103 =

b. 1.0 x 103 =

CH3CH2COO- =1.0 x 103 x 0.1 M = 1.0 x 102 M or 100 M

CHM 380

Fall 2013

B) Isobutylamine (

), pKa = 10.56

a. Acid:

+
3

Base: [C4 H 9 NH 2] [C4 H 9 NH 3+ ] [C4 H 9 NH 2] [C4 H 9 NH 3+ ]

b. pH = pKa + log

7.86 = 10.56 + log

-2.70 = log

[C4 H 9 NH 2] [C4 H 9 NH 3+ ] [C4 H 9 NH 2] [C4 H 9 NH 3+ ]

2.0 x 10-3 =

c. 2.0 x 10-3 =

[C4 H 9 NH 2] (0.1M )

C4H9NH2 =2.0 x 10-3 x 0.1 M = 2.0 x 10-4 M 2. Draw hydrogen bonding between the following pairs of molecules. Draw a dashed line from the hydrogen being donated and the hydrogen bond acceptor a. Two water molecules

HOH HOH

CHM 380

Fall 2013

b. Water & 3-Pentanone (

HOH

c. Phenylacetic acid (

) and 1-propylamine (

)(Draw two

possible answers to this question; remember, a carboxylic acid can be a hydrogen bond donor OR acceptor)
H
O CH2

H CH2 CH2 CH3 CH2 O H N CH2 CH2 CH3

OH

OH

3. For the following pairs of compounds, draw the product formed by their acid catalyzed condensation. Identify the category of organic compound the product falls into:

A.

Ester
B. +

Amide (primary)

CHM 380

Fall 2013

C.

Amide (secondary)

D.

+ 1

Hemiacetal

CHM 380

Fall 2013

4.

Identify the following structures as:

A.

Fatty acid Triacylglycerol Steroid B.

Sphingolipid Phospholipid

Steroid
C. D.

Phospholipid

Sphingolipid
E

Triglyceride

Fatty Acid

CHM 380

Fall 2013

5. Draw the structure of the a phosphatidylethanolamine containing oleic acid and lauric acid

oleic acid

lauric acid
H

ethanolamine
CH2 O
-

OH

P O-

O-

CH

OH

CH2

OH

Phosphate

Glycerol

CH2

O O

O O H2N OP O

CH CH2