Organic Chemistry
Organic Chemistry
4th Edition
ISBN: 9780073402772
Author: Janice G. Smith
Publisher: MCG
Question
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Chapter 10, Problem 10.68P
Interpretation Introduction

(a)

Interpretation: The synthesis of each product from the given starting material having more than one step is to be predicted.

Concept introduction: The reaction of alkene with halogen and water results in the formation of halohydrin product.

The addition of Halogens to alkenes is a stereospecific reaction. The resultant product is meso compound, if alkene is cis and addition of halogen is syn addition. If addition of halogen is anti, then the resultant products are racemic mixture. In case of trans alkene, the resultant product is meso, if addition of halogen is anti. The resultant products are racemic mixture, if the addition of halogen is syn.

Interpretation Introduction

(b)

Interpretation: The synthesis of each product from the given starting material having more than one step is to be predicted.

Concept introduction: Electrophilic addition reaction follows markovnikov rule.

According to markovnikov rule, the positive part of halogen acid attached to that carbon atom in C=C bond which carries higher number of hydrogen atoms and the negative part of halogen acid will attach to that carbon atom in C=C bond which has lesser number of hydrogen atoms.

Interpretation Introduction

(c)

Interpretation: The synthesis of each product from the given starting material having more than one step is to be predicted.

Concept introduction: Hydroboration reaction is a two step reaction, which involves conversion of alkene into alcohol. This type of reaction follows anti-markovnikov rule.

Anti-markovnikov rule states that the positive part of acid attached to that carbon atom in C=C bond which carries lesser number of hydrogen atoms and the negative part of acid will attach to that carbon atom in C=C bond which has higher number of hydrogen atoms.

Interpretation Introduction

(d)

Interpretation: The synthesis of each product from the given starting material having more than one step is to be predicted.

Concept introduction: The reaction of alkene with halogen and water results in the formation of halohydrin product.

The addition of Halogens to alkenes is a stereospecific reaction. The resultant product is meso compound, if alkene is cis and addition of halogen is syn addition. If addition of halogen is anti, then the resultant products are racemic mixture. In case of trans alkene, the resultant product is meso, if addition of halogen is anti. The resultant products are racemic mixture, if the addition of halogen is syn.

Interpretation Introduction

(e)

Interpretation: The synthesis of each product from the given starting material having more than one step is to be predicted.

Concept introduction: The reaction of alkene with halogen and water results in the formation of halohydrin product.

The addition of Halogens to alkenes is a stereospecific reaction. The resultant product is meso compound, if alkene is cis and addition of halogen is syn addition. If addition of halogen is anti, then the resultant products are racemic mixture. In case of trans alkene, the resultant product is meso, if addition of halogen is anti. The resultant products are racemic mixture, if the addition of halogen is syn.

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Chapter 10 Solutions

Organic Chemistry

Ch. 10 - Linolenic acidTable 10.2 and stearidonic acid are...Ch. 10 - Prob. 10.12PCh. 10 - Prob. 10.13PCh. 10 - Prob. 10.14PCh. 10 - Prob. 10.15PCh. 10 - Prob. 10.16PCh. 10 - Prob. 10.17PCh. 10 - Prob. 10.18PCh. 10 - Prob. 10.19PCh. 10 - Which compounds A-D in Figure 10.12 are formed by...Ch. 10 - What two alkenes give rise to each alcohol as the...Ch. 10 - Prob. 10.22PCh. 10 - Problem 10.23 Draw the products of each reaction,...Ch. 10 - Problem 10.24 Draw all stereoisomers formed in...Ch. 10 - Prob. 10.25PCh. 10 - Prob. 10.26PCh. 10 - Borane is sold for laboratory use as a complex...Ch. 10 - What alkylborane is formed from hydroboration of...Ch. 10 - Draw the products formed when each alkene is...Ch. 10 - What alkene can be used to prepare each alcohol as...Ch. 10 - Prob. 10.31PCh. 10 - Draw the products of each reaction using the two...Ch. 10 - Problem 10.31 Devise a synthesis of each compound...Ch. 10 - Give the IUPAC name for each compound. a.b.Ch. 10 - a Label the carbon-carbon double bond in A as E or...Ch. 10 - Prob. 10.36PCh. 10 - Calculate the number of degrees of unsaturation f...Ch. 10 - Prob. 10.38PCh. 10 - The fertility drug clomiphene trade name Clomid is...Ch. 10 - Give the IUPAC name for each compound. a....Ch. 10 - Give the structure corresponding to each name. a....Ch. 10 - 10.40 (a) Draw all possible stereoisomers of, and...Ch. 10 - Prob. 10.43PCh. 10 - 10.42 Now that you have learned how to name...Ch. 10 - Prob. 10.45PCh. 10 - Prob. 10.46PCh. 10 - Prob. 10.47PCh. 10 - Prob. 10.48PCh. 10 - By using the bond dissociation energies in...Ch. 10 - Prob. 10.50PCh. 10 - Repeat Problem 10.50 with CH32C=CH2 as the...Ch. 10 - What alkene can be used to prepare each alkyl...Ch. 10 - Prob. 10.53PCh. 10 - Draw the constitutional isomer formed in each...Ch. 10 - Prob. 10.55PCh. 10 - Draw all stereoisomers formed in each reaction....Ch. 10 - Prob. 10.57PCh. 10 - Prob. 10.58PCh. 10 - Prob. 10.59PCh. 10 - Draw a stepwise mechanism for the following...Ch. 10 - Draw a stepwise mechanism for each reaction. a.b.Ch. 10 - Draw a stepwise mechanism that shows how all three...Ch. 10 - Less stable alkenes can be isomerized to more...Ch. 10 - Prob. 10.64PCh. 10 - Prob. 10.65PCh. 10 - Bromoetherification, the addition of the elements...Ch. 10 - Devise a synthesis of each product from the given...Ch. 10 - Prob. 10.68PCh. 10 - Prob. 10.69PCh. 10 - Prob. 10.70PCh. 10 - 10.66 Explain why A is a stable compound but B is...Ch. 10 - Prob. 10.72PCh. 10 - Prob. 10.73PCh. 10 - 10.69 Lactones, cyclic esters such as compound A,...Ch. 10 - 10.70 Draw a stepwise mechanism for the following...Ch. 10 - 10.71 Like other electrophiles, carbocations add...Ch. 10 - 10.72 Draw a stepwise mechanism for the...
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