1. A Review of General Chemistry

In 1934, Edward A. Doisy of Washington University extracted 3000 lb of hog ovaries to isolate a few milligrams of pure estradiol, a potent female hormone. Doisy burned 5.00 mg of this precious sample in oxygen and found that 14.54 mg of CO₂ and 3.97 mg of H₂O were generated.

b. The molecular weight of estradiol was later determined to be 272. Determine the molecular formula of estradiol.

Compound X, isolated from lanolin (sheep's wool fat), has the pungent aroma of dirty sweatsocks. A careful analysis showed that compound X contains 62.0% carbon and 10.4% hydrogen. No nitrogen or halogen was found.

b. A molecular weight determination showed that compound X has a molecular weight of approximately 117. Find the molecular formula of compound X.

Give the molecular formula of each compound shown

(a)

(b)

(c)

Some of the following molecular formulas correspond to stable compounds. When possible, draw a stable structure for each formula. Propose a general rule for the numbers of hydrogen atoms in stable hydrocarbons.

Convert the following hybrid structural formulas into the line-angle drawings.

(b)

Given the line-angle drawings shown, answer the following questions:

(i) How many carbons are in each molecule?

(ii) How many hydrogens are at the circled carbon?

(iii) Is the indicated (→) carbon or 1° , 2°, 3°, or 4°?

(f)

Identify the mistakes contained within the following structures.

(a)

How many hydrogens are attached to each of the indicated carbons in morphine?

How many hydrogens would you expect a 24-carbon compound from each of the following molecular classes to have?

(a) Alkane

For each of the following line-angle drawings,

(i) give the number of carbons,

(ii) label the carbons,

(iii) tell how many hydrogens are on each carbon, and

(iv) draw the hybrid structural formula.

(c)

For each of the following line-angle drawings, 

(i) give the number of carbons, 

(ii) label the carbons, 

(iii) tell how many hydrogens are on each carbon, and 

(iv) draw the hybrid structural formula.

(d)

Given the line-angle drawings shown, answer the following questions:

(i) How many carbons are in each molecule?

(ii) How many hydrogens are at the circled carbon?

(iii) Is the indicated (→) carbon or 1° , 2°, 3°, or 4°?

(c)

For each of the following line-angle drawings, 

(i) give the number of carbons, 

(ii) label the carbons, 

(iii) tell how many hydrogens are on each carbon, and 

(iv) draw the hybrid structural formula.

(b)

Draw the structure of a hydrocarbon that has six carbon atoms and

a. three vinylic hydrogens and two allylic hydrogens.

b. three vinylic hydrogens and one allylic hydrogen.

c. three vinylic hydrogens and no allylic hydrogens.