Organic Compounds and the Atomic Properties of Carbon

Draw correct structures, by making a single change for any that are incorrect:

(a)  

(b)

(c)

(d)

Question: Draw all possible skeletons for a 7-C compound with

(a) A 6-C chain and 1 double bond

(b) A 5-C chain and 1 double bond

(c) A 5-C ring and no double bonds

Explain how a polarimeter works and what it measures.

Among alkenes, alkynes and aromatic hydrocarbons, only alkenes exhibit cis-trans isomerism. Why don’t the others?

Define each type of isomer: (a) constitutional; (b) geometric; (c) optical. Which types of isomers are stereoisomers?

(a) What structural feature is associated with each type of hydrocarbon; an alkane; a cycloalkane; an alkene; an alkyne? (b) Give the general formula for each type.(c) Which hydrocarbons are considered saturated?

Which of these bonds to carbon would you expect to be relatively reactive: $\mathbf{C}\mathbf{-}\mathbf{H}\mathbf{,}\mathbf{C}\mathbf{-}\mathbf{C}\mathbf{,}\mathbf{C}\mathbf{-}\mathbf{I}\mathbf{,}\mathbf{C}\mathbf{=}\mathbf{O}\mathbf{,}\mathbf{C}\mathbf{-}\mathbf{Li}$? Explain.

What is the range of oxidation states for carbon? Name a compound in which carbon has its highest oxidation state and one in which it has its lowest.

Silicon lies just below carbon in Group 4A (14) and also forms four covalent bonds. Why aren’t there as many silicon compounds as carbon compounds?

Carbon bonds to many elements other than itself.(a) Name six elements that commonly bond to carbon in inorganic compounds. (b) Which of these elements are heteroatoms?(c) Which of these elements are more electronegative than carbon? Less electronegative?(d) How does bonding of carbon to heteroatoms increase the number of organic compounds?

Explain each statement in terms of atomic properties:(a) Carbon engages in covalent rather than ionic bonding. (b) Carbon has four bonds in all its organic compounds.(c) Carbon forms neither stable cations, like many metals, nor stable anions, like many nonmetals.(d) Carbon bonds to itself more extensively than does any other element. (e) Carbon forms stable multiple bonds.

Give the names and formulas of two carbon compounds that are organic and two that are inorganic.

Write equations for the following: (a) an addition reaction between ${\mathbf{H}}_{\mathbf{2}}\mathbf{O}$ and 3-hexene ( ${\mathbf{H}}^{\mathbf{+}}$ is a catalyst); (b) an elimination reaction between 2-bromopropane and hot potassium ethoxide, ${\mathbf{CH}}_{\mathbf{3}}\mathbf{-}{\mathbf{CH}}_{\mathbf{2}} \mathbf{-}\mathbf{OK}$( KBr and ethanol are also products); (c) a light-induced substitution reaction between and ethane to form 1,2-dichloroethane.

Determine the type of each of the reactions:

Is the organic reactant oxidized, reduced, or neither in each of the following reactions?

Question: Is the organic reactant oxidized, reduced, or neither in each of the following reactions?

What linkage joins the monomers in each strand of DNA? 

Draw the R group of (a) alanine; (b) histidine; (c) methionine.

Draw the R group of (a) glycine; (b) isoleucine; (c) tyrosine.

Write the sequence of the complementary DNA strand that pairs with each of the following DNA base sequences: 

(a) TTAGCC 

(b) AGACAT

Write the sequence of the complementary DNA strand that pairs with each of the following DNA base sequences:

(a) GGTTAC 

(b) CCCGAA

Write the base sequence of the DNA template from which this RNA sequence was derived: UGUUACGGA. How many amino acids are coded for in this sequence?

Write the base sequence of the DNA template from which this RNA sequence was derived: GUAUCAAUGAACUUG. How many amino acids are coded for in this sequence?

Protein shapes are maintained by a variety of forces that arise from interactions between the amino-acid R groups. Name the amino acid that possesses each R group and the force that could arise in each of the following interactions:

(a)

(b)

(c)

(d)

Some of the most useful compounds for organic synthesis are Grignard reagents (general formula , where X is a halogen), which are made by combining an alkyl halide, , with. They are used to change the carbon skeleton of a starting carbonyl compound in a reaction similar to that with :

(a) What is the product, after a final step with water, of the reaction between ethanal and the Grignard reagent of bromobenzene? 

(b) What is the product, after a final step with water, of the reaction between 2-butanone and the Grignard reagent of 2-bromopropane? 

(c) There are often two (or more) combinations of Grignard reagent and carbonyl compound that will give the same product. Choose another pair of reactants to give the product in (a). 

(d) What ±OH group at the end of the carbon chain? 

(e) What Grignard carbonyl compound must react with a Grignard reagent to yield a product with the reagent and carbonyl compound would you use to prepare 2-methyl-2-butanol?

Some of the most useful compounds for organic synthesis are Grignard reagents (general formula$\mathbf{R}\mathbf{-}\mathbf{MgX}$ , where X is a halogen), which are made by combining an alkyl halide,$\mathbf{R}\mathbf{-}\mathbf{X}$ , with. They are used to change the carbon skeleton of a starting carbonyl compound in a reaction similar to that with $\mathbf{R}\mathbf{-}\mathbf{Li}$:

(a) What is the product, after a final step with water, of the reaction between ethanal and the Grignard reagent of bromobenzene? 

(b) What is the product, after a final step with water, of the reaction between 2-butanone and the Grignard reagent of 2-bromopropane? 

(c) There are often two (or more) combinations of Grignard reagent and carbonyl compound that will give the same product. Choose another pair of reactants to give the product in (a). 

(d) What carbonyl compound must react with a Grignard reagent to yield a product with the ±OH group at the end of the carbon chain? 

(e) What Grignard reagent and carbonyl compound would you use to prepare 2-methyl-2-butanol?

Question: Which features of the retinal make it so valuable as a photon absorber in the visual systems of organisms?

Question: Pyrethrins, such as jasmolin II (below), are a group of natural compounds synthesised by flowers of the genus Chrysanthemum (known as pyrethrum flowers) to act as insecticides. 

(a) Circle and name the functional groups in jasmolin II. 

(b) What is the hybridization of the numbered carbons? 

(c) Which, if any, of the numbered carbons are chiral centers?

Question: Ibuprofen is one of the most common anti-inflammatory drugs. 

(a) Identify the functional group(s) and chiral center(s) in ibuprofen. 

(b) Write a four-step synthesis of a racemic mixture of ibuprofen from 4-isobutyl benzaldehyde, using inorganic reactants and one organometallic reactant (see Problem 15.107).

Which features of the retinal make it so valuable as a photon absorber in the visual systems of organisms?

Ibuprofen is one of the most common anti-inflammatory drugs. 

(a) Identify the functional group(s) and chiral center(s) in ibuprofen. 

(b) Write a four-step synthesis of a racemic mixture of ibuprofen from 4-isobutyl benzaldehyde, using inorganic reactants and one organometallic reactant (see Problem 15.107).

Pyrethrins, such as jasmolin II (below), are a group of natural compounds synthesised by flowers of the genus Chrysanthemum (known as pyrethrum flowers) to act as insecticides. 

(a) Circle and name the functional groups in jasmolin II. 

(b) What is the hybridization of the numbered carbons? 

(c) Which, if any, of the numbered carbons are chiral centers?