2. Molecular Representations

Functional Groups

2. Molecular Representations

Functional Groups

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Why we need functional groups.

Recognizing different types of hydrocarbons.

How to assign degrees to carbons and hydrogens.

Determine the degree of the indicated carbons and hydrogens.

Recognizing alkyl halides.

Assigning Degrees to Alkyl Halides

How to recognize alcohols, amines and ethers.

How to recognize carboxylic acids, amides and esters.

The difference between aldehydes and ketones.

How to write the condensed structures for aldehydes and ketones.

How to recognize nitriles.

The difference between phenyl and benzyl groups.

Identifying Functional Groups

Recognizing acyl chlorides and anhydrides.

Recognizing sulfur compounds

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Practice this topic

Multiple Choice

PRACTICE:The following molecule contains several functional groups. Of the choices given, select the most appropriate answer (not all functional groups may be listed).

PRACTICE:Identifying functional groups. Select the most appropriate answer.

PRACTICE:Identifying functional groups. Select the most appropriate answer.

How many secondary carbon atoms are in the following molecule?

Which of the following is an alkene?

Which functional group is an ether?

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Textbook Question

Draw a Lewis structure, and classify each of the following compounds. The possible classifications are as follows: alcohol ether ketone aldehyde carboxylic acid alkene a. CH2CHCHO b. CH3CH2CH(OH)CH3 c. CH3COCH2CH3

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Textbook Question

Circle the functional groups in the following structures. State to which class (or classes) of compounds the structure belongs. a. CH2=CHCH2COOCH3 b. CH3OCH3 c. CH3CHO

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Textbook Question

Circle the functional groups in the following structures. State to which class (or classes) of compounds the structure belongs. d. CH3CONH2 e. CH3NHCH3 f. RCOOH

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Textbook Question

Draw a Lewis structure, and classify each of the following compounds: m.

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Textbook Question

Draw a Lewis structure, and classify each of the following compounds: k.

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Textbook Question

Draw a Lewis structure, and classify each of the following compounds: i.

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Textbook Question

Draw a Lewis structure, and classify each of the following compounds. The possible classifications are as follows: alcohol ether ketone aldehyde carboxylic acid alkene h.

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Textbook Question

Circle the functional groups in the following structures. State to which class (or classes) of compounds the structure belongs. g. h. i.

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Textbook Question

Draw a Lewis structure, and classify each of the following compounds: e. (CH3CH2)2O f. CH3CH2CH2CN

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Textbook Question

Draw a Lewis structure, and classify each of the following compounds: c. (CH3)2CHCOOCH3 d. CH3CHCHCOCl

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Textbook Question

Draw a Lewis structure, and classify each of the following compounds: a. CH3CH2CONHCH3 b. (CH3CH2)2NH

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Textbook Question

Draw a Lewis structure, and classify each of the following compounds. The possible classifications are as follows: alcohol ether ketone aldehyde carboxylic acid alkene f. g.

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Textbook Question

Draw a Lewis structure, and classify each of the following compounds. The possible classifications are as follows: alcohol ether ketone aldehyde carboxylic acid alkene d. CH3CH2OCHCH2 e.

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Textbook Question

Classify the following hydrocarbons, and draw a Lewis structure for each one. A compound may fit into more than one of the following classifications: alkane alkene alkyne cycloalkane cycloalkene cycloalkyne aromatic hydrocarbon g. h. i.

a. How many primary carbons does each of the following compounds have? b. How many secondary carbons does each one have? c. How many tertiary carbons does each one have? 1.

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Textbook Question

Are the following compounds primary, secondary, or tertiary? a.

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Textbook Question

(•••) Identify the functional groups in each of the following molecules. [The number of functional groups has been given to assist you.] (d) [Two]

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Textbook Question

(•••) Identify the functional groups in each of the following molecules. [The number of functional groups has been given to assist you.] (b) [Two]

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Textbook Question

(•••) Identify the functional groups in each of the following molecules. [The number of functional groups has been given to assist you.] (a) [Three]

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Textbook Question

When we begin studying reactive intermediates, the designation of substitution will be especially important. Label the following carbocations as 1° , 2°, 3°, or 4° or based on the carbon bearing the positive charge. (c)

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Textbook Question

(•) 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°? (h)

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Textbook Question

(•••) Identify the functional groups in each of the following molecules. [The number of functional groups has been given to assist you.] (c) [Three]

Classify each hydrogen atom in the following compounds as primary (1°), secondary (2°), or tertiary (3°). c. 2-methylbutane d. cyclohexane

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Textbook Question

Label each hydrogen atom in the following compounds as primary (1°), secondary (2°), or tertiary (3°). e. f.

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Textbook Question

Label each hydrogen atom in the following compounds as primary (1°), secondary (2°), or tertiary (3°). c. (CH3)2CHCH(CH3)CH2CH3 d.

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Textbook Question

Classify each hydrogen atom in the following compounds as primary (1°), secondary (2°), or tertiary (3°). e. norbornane (bicyclo[2.2.1]heptane)

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Textbook Question

How many carbons are in the planar double-bond system in each of the following compounds? a.

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Textbook Question

How many carbons are in the planar double-bond system in the following compound?

Label each sulfhydryl group asprimary (1°) secondary (2°) , or tertiary (3°)

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Textbook Question

Identify the substitution of carbons (a)–(d) comprising the ether functional group in the following molecules. (a) (b) (c) (d)

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Textbook Question

Label each hydroxyl group in Assessment 13.6 as primary (1°) secondary (2°) , or tertiary (3°)

In 2012, a group led by Professor Masayuki Satake of the University of Tokyo reported the isolation and structure determination of a toxin from a marine algal bloom that decimated the fish population off the New Zealand coast in 1998. Extensive mass spectrometry and NMR experiments ultimately led to the structure shown below, named Brevisulcenal-F. (See Journal of the American Chemical Society, 2012, 134, 4963–4968.) This structure holds the record for the largest number of fused rings, at 17.

(a) How many ether groups are present? (b) How many alcohol groups are present? Classify the alcohols as 1° or 2° or 3°. (c) Are there any other oxygen-containing functional groups? Which, if any?

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Textbook Question

Given the molecular formula, (i) what functional groups are possible in each of the following molecules? (b) C₆H₁₀O

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Textbook Question

Given the molecular formula, (i) what functional groups are possible in each of the following molecules? (a) C₆H₁₄O

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Textbook Question

Label the amines shown as a 1° amine, 2° amine, 3° amine, or 4° ammonium ion.

a. <IMAGE>

b. <IMAGE>

c. <IMAGE>

d. <IMAGE>

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Textbook Question

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

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Textbook Question

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

(b) Alkene

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Textbook Question

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

(a) Alkane

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Textbook Question

a. How many hydrogens does an alkane with 17 carbons have?

b. How many carbons does an alkane with 74 hydrogens have?

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Textbook Question

a. How many primary carbons does each of the following compounds have?

b. How many secondary carbons does each one have?

c. How many tertiary carbons does each one have?

2. <IMAGE>

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Textbook Question

Macrolide antibiotics all have large rings (macrocycle) in which

an ester makes the ring; a cyclic ester is termed a lactone.

One example is erythromycin A, first isolated from soil bacteria

in the 1950s. Over time, some pathogenic bacteria

have developed resistance to erythromycin by evolving

an enzymatic mechanism to cleave the macrocycle

at the ketone.

To counter this resistance, chemists modified the erythromycin

structure to replace the ketone with an amine that the bacteria

could not detoxify. This modified antibiotic, azithromycin,

trade name Zithromax®, is one of the most prescribed

drugs in the world for respiratory infections.

<IMAGE>

as the site for detoxification.

(d) Identify the amine in azithromycin. What type of amine is it?

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Textbook Question

Draw a Lewis structure, and classify each of the following compounds:

g. (CH3)3CCH2CH2COOH

h. <IMAGE>

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Textbook Question

Many naturally occurring compounds contain more than one functional group. Identify the functional groups in the following compounds:

a. Penicillin G is a naturally occurring antibiotic. <IMAGE>

b. Dopamine is the neurotransmitter that is deficient in Parkinson’s disease. <IMAGE>

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Textbook Question

Many naturally occurring compounds contain more than one functional group. Identify the functional groups in the following compounds:

d. Thyroxine is the principal thyroid hormone.

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Textbook Question

There are eight different five-carbon alkyl groups. c. In each case, label the degree of substitution (primary, secondary, or tertiary) of the head carbon atom bonded to the main chain.

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Textbook Question

When we begin studying functional groups, the designation of substitution will be especially important. Label the following bromoalkanes as 1° , 2°, 3°, or 4° based on the carbon to which the bromine is attached. (b)

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<p>Hydrocarbons</p>

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