1. Read Chapter 1 in M&B

CHE 300 Homework # 1

1. Read Chapter 1 in M&B.

2. Do problems: 1.1 (a,b,c,d) page 5

1.2 (a,b,c,d)

1.3 (b,c) page 8

3. Define the following terms:

organic chemistry

chemical bond

ionic bond

covalent bond

atomic orbital

Pauli exclusion principle

Atomic number

isotopes

atomic weight

4. For the following molecules, give the hybridization used in the bonding and the bond angles.

BeCl2 BCl3 CCl4 BF4-

5. Give the spectral notation (1s2 2s2 etc.) for a neutral atom of Bromine (atomic number 35. How many valence elctrons?

CHE 300 Homework # 2

1. Define:

hydrogen bonding

Lowry-Bronsted acid

Lowry-Bronsted base

Lewis acid

Lewis base

isomers

2. In M&B do the following problems:

1.6 p. 26

1.9 (a,b) p. 35

1.10 (a,b,c,d)

1.11 (a,b)

5 (a thru f) p.37

9 (a,d) Note: (aq) stands for an aqueous solution. This

problem asks for the actual acids and bases

involved, i.e., HCl(aq) is actually H3O+ and Cl-

dissolved in water.

3. Predict the shape of each of the following. Indicate the hybridization of the central atom and the approximate bond angles:

NH4+ NH3 H3O+ CH3+ CH3:- H2S

CHE 300 Homework # 3

1. Name the following structures:

CH4 CH3Cl CH2Cl2 CHCl3

2. Complete the following reactions showing all important products. It is not necessary to balance the equations. If no reaction takes place with the reagents or under the conditions shown, write N.R.

flame

A) CH4 + (xs) O2 ----->

1500o

B) (xs) CH4 + O2 ----->

850o

C) CH4 + H2O ----->

D) CH4 + Br2 ----->

heat

E) CH4 + Cl2 ----->

F) CH4 + I2 ----->

heat

G) CH4 + (xs) Br2 ----->

3. Write out the complete mechanism for the reaction of methane with chlorine. Label the initiating, propagating, and terminating steps.

4. Calculate the delta H for the overall reaction in question 3.

5. Calculate the delta H for each step in the mechanism in 3.

CHE 300 Homework # 4

1. In M&B do problems:

2.1 (a) p.50

2.2 (a)

11 (e) p.76

12 (a)

2. Graph the potential energy changes for the rate determining step (RDS) in 2.2 (a) above. Label both axes, Eact, delta H, reactants, products, etc.

3. What are the three factors that influence the rate of a chemical reaction?

4. Eact may be estimated from a known delta H. If the delta H is -13 Kcal/mole, estimate the Eact.

If delta H is +13 Kcal/mole?

5. Draw a probable structure for the transition state of the RDS in 2.2 (a) above.

6. Draw and give the names for the nine isomeric heptanes (C7H16).

7. In M&B do problem 1 (a,b,d) p. 122

8. Name the following structures:

CH3 CH3

| |

CH3CHCH3 CH3CH2CH2CH2CH2CH3 CH2CH2CH3

CH3

CH2 CH3 CH2CH3

| | |

CH3CHCH3 CH3C-CH2-C-CH2CH2CH3

| |

H CH2CH3

CHE 300 Homework # 5

1. Draw Newman projections for all STABLE conformations about the C2-C3 bond in This was Font/Pitch 1,10 - Off.This was Font/Pitch 4,10 - On.nThis was Font/Pitch 4,10 - Off.This was Font/Pitch 1,10 - On.-butane.

2. In M&B do problems:

3.1 p. 84

3.9 p. 101

3.10

3.11 (a)

2 (f,l) p. 123 (hint: longest chain?)

3. Complete the following reactions:

A) ethyl bromide + Mg ---->

B) Product of A + water ---->

C) ethyl bromide + Zn + acid ---->

D) isopropyl bromide + Li ---->

E) product from D + CuI ---->

F) product from E + ethyl bromide ---->

4. Make a table listing the names of the methods that can be used in the synthesis of an alkane (hydrogenation of an alkene, etc.) and an example set of reactions for each.

CHE 300 Homework # 6

1. In M&B do problems:

3.12 p. 105

3.13

p. 123

9 (a,b,c)

10 (circle the product(s) formed the fastest)

2. List all steps in the general mechanism for halogenation of an alkane. Label the initiating, propagating, and terminating steps. Label the RDS.

3. Make a table showing the names of all of the reactions that alkanes are expected to undergo (halogenation, etc.) and give an example reaction for each.

CHE 300 Homework # 7

1. In M&B do problems:

p. 162: 1 (all);

p. 136: 4.5 (a,b,c,d);

2. Specify R or S for the following:

CH3 CH2CH3

| |

A) CH3CH2--+--H B) CH3--+--Br

| |

Cl H

CH2Cl CH3

| |

C) H--+--CH3 D) Br--+--CH2CH3

| |

OH OH

Answer: All are S! Make models and see why!

3. In M&B do problems:

4.12 (a,b,h); p. 147

4.13

CHE 300 Homework # 8

1. In M&B do the following problems:

p. 211

4 (a thru f)

5 (a,c)

2. Show the stereochemistry of the product of the following reaction:

C6H13

| NaOH

H---+---Br ------>

| SN2

CH3

3. Outline all steps in syntheses of each of the following from your choice of starting material. Use a different method in each case.

Ethyl chloride

isopropyl bromide

n-propyl iodide

isobutyl bromide

4. Make a table showing all of the ways that you can synthesize an alkyl halide and give an example of each.

5. Make a table showing all of the reactions of alkyl halides.

CHE 300 Homework # 9

In M&B do problems:

5.8;

p. 212:

6; 7; 8;

p. 271:

4 (i,j);

Outline all steps in each of the following mechanisms:

a) SN2

b) SN1

label the RDS in each of the above mechanisms.

Show the stereochemistry of the product of the following reaction:

C6H13

| dil. NaOH

H---+---Br ------>

| SN1

CH3

Predict the product(s) of the following reaction:

dil. NaOH

neopentyl bromide ------>

SN1

CHE 300 Homework #10

Predict the products of the reactions of isopropyl alcohol with:

a) cold, conc. sulfuric acid

b) con. HBr

c) NaBr,H2SO4

d) P,I2

e) PBr3

f) K (Potassium metal)_

g) methyl magnesium bromide

h) sodium hydroxide

i) sodium bicarbonate

j) H2/Ni

k) Br2,CCl4

l) K2CrO7

m) NaOCl

n) acetic acid (CH3COOH),H+

o) CH3COCl

p) CH3SO2Cl

Read "All about syntesis" p. 247;

Problem 17;

Outline all steps in the mechanisms of the following. Label the RDS in each:

Reaction of a primary alcohol with HX.

Reaction of a tertiary alcohol with HX.

Complete the following reaction:

3,3-dimethyl-2-butanol + HCl ----->

CHE 300 Homework # 11

p. 245 2;3;7;18

8.1(a);

8.3(a);

______

CHE 300 Homework # 12

In M&B do problems:

8.5 (a,b,c,d);

8.6 (a,b,c,d), note the word PURE!

8.9;

Outline all steps in each of the following general mechanisms. Label the RDS's.

1) E2

2) SN2

3) SN1

CHE 300 Homework # 13

1. Outline all steps in each of the following mechanisms. Label RDS.

A) E2

B) E1

2. Complete the following reactions. Circle major product.

A) CH3CH2CH2CH2OH + H2SO4 ---->

B) CH3CH2CH2CH2Br + KOH(alc.) ---->

3. In M&B do problems:

p. 316:

5 (a,b,c,e);

6 (a,c,d,e);

4. How do you account for the products of the following reaction?

H+

neopentyl alcohol ----> 2-methyl-1-butene + 2-methyl-2-butene

5. Outline all steps in a possible laboratory synthesis of ethylene from ethane.

6. Make a table showing all of the ways to make an alkene and give one example of each.

CHE 300 Homework # 14

In M&B do problems:

p. 363

1 (a thru j);

3 (a,b,c,d,e,g);

20 (a,b,c);

21 (a,b,e);

Outline all steps in the mechanism for the addtion of HX to an alkene. Label the RDS.

CHE 300 Homework # 15

1. In M&B do problems:

p. 363:

1 (k thru t);

16 (a,b,c);

20 (d,e,f);

21 (c,d,f,g);

2. Reactions:

A) 2-methyl-1-butene + Br2,H2O ----->

B) 3-methyl-1-butene + H2O,H+ ----->

C) 2-methyl-2-butene + HCl ----->

3. Mechanisms.

A) Addition of water to an alkene in the presence of an acid.

B) Addition of HBr to an alkene in the presence of peroxides.

4. Make a table showing all of the reactions of alkenes with examples for each.

CHE 300 Homework # 16

10.1;

10.3;

10.4.

______

CHE 300 Homework # 17

1. In M&B do problems:

11.11;

11.16;

p. 422:

3 (a,b,c,d,e,g);

4 (a,c,e).

2. Nomenclature:

CH2=CH-CH=CH-CH=CH2

3. Reactions:

A) CH2=CH-CH=CH2 + Br2,H2O ----->

B) CH2=CH-CH=CH2 + HBr ----->

C) CH2=CH-CH=CH2 + HBr,peroxides ----->

CHE 300 Homework # 18

In M&B do problems:

p. 441:

1 (a,b,c);

2( a,b,c,d,f);

4 (all).

CHE 300 Homework 19

In M&B do problems:

13.1;

13.6 (e);

p. 489:

1 (a,b,c,d);

2 (a thru s).

CHE 300 Homework # 20

In M&B:

p. 489:

2 (t-cc);

13.27;

13.25;

16 (a,b,c,g,h,j).