Organic Chemistry
Organic Chemistry
4th Edition
ISBN: 9780073402772
Author: Janice G. Smith
Publisher: MCG
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Chapter 21, Problem 21.45P
Interpretation Introduction

(a)

Interpretation:

The product formed on treatment of phenylacetaldehyde with given reagent is to be predicted.

Concept introduction:

Sodiumborohydride is a metal reducing agent. It reduces ketones and aldehyde into secondary alcohols and primary alcohols respectively.

Expert Solution
Check Mark

Answer to Problem 21.45P

The product formed on treatment of phenylacetaldehyde with given reagent is,

Organic Chemistry, Chapter 21, Problem 21.45P , additional homework tip  1

Explanation of Solution

In the presence of sodium borohydride and methanol, phenylacetaldehyde gets reduced to 2-phenylethanol. The corresponding chemical reaction is shown below.

Organic Chemistry, Chapter 21, Problem 21.45P , additional homework tip  2

Figure 1

Conclusion

The product formed on treatment of phenylacetaldehyde with given reagent is shown in figure 1.

Interpretation Introduction

(b)

Interpretation:

The product formed on treatment of phenylacetaldehyde with given reagent is to be predicted.

Concept introduction:

Lithium aluminum hydride is a strong reducing agent. Treatment of carbonyl compounds with lithium aluminum hydride followed by water yields alcohols. It reduces aldehyde into primary alcohol.

Expert Solution
Check Mark

Answer to Problem 21.45P

The product formed on treatment of phenylacetaldehyde with given reagent is,

Organic Chemistry, Chapter 21, Problem 21.45P , additional homework tip  3

Explanation of Solution

In the presence of lithium aluminium hydride followed by hydrolysis, phenylacetaldehyde gets reduced to 2-phenylethanol. The corresponding chemical reaction is shown below.

Organic Chemistry, Chapter 21, Problem 21.45P , additional homework tip  4

Figure 2

Conclusion

The product formed on treatment of phenylacetaldehyde with given reagent is shown in figure 2.

Interpretation Introduction

(c)

Interpretation:

The product formed on treatment of phenylacetaldehyde with given reagent is to be predicted.

Concept introduction:

Grignard reagents are organometallic compounds which are prepared using alkyl halides in presence of magnesium metal in dry ether. These reagents act as strong nucleophiles and bases.

Expert Solution
Check Mark

Answer to Problem 21.45P

The product formed on treatment of phenylacetaldehyde with given reagent is,

Organic Chemistry, Chapter 21, Problem 21.45P , additional homework tip  5

Explanation of Solution

In the presence of Grignard reagent followed by hydrolysis, phenylacetaldehyde forms primary alcohol. The corresponding chemical reaction is shown below.

Organic Chemistry, Chapter 21, Problem 21.45P , additional homework tip  6

Figure 3

The product formed is 1-phenylpropan-2-ol.

Conclusion

The product formed on treatment of phenylacetaldehyde with given reagent is shown in figure 3.

Interpretation Introduction

(d)

Interpretation:

The product formed on treatment of phenylacetaldehyde with given reagent is to be predicted.

Concept introduction:

Nucleophilic addition reaction is a type of organic reaction in which the nucleophile is added to an electrophilic site. In case of carbonyl compounds, the carbonyl carbon acts as an electrophilic site.

Expert Solution
Check Mark

Answer to Problem 21.45P

The product formed on treatment of phenylacetaldehyde with given reagent is,

Organic Chemistry, Chapter 21, Problem 21.45P , additional homework tip  7

Explanation of Solution

Phenylacetaldehyde reacts with sodium cyanide followed by protonation to form 2-hydroxy-3-phenylpropanenitrile. The corresponding chemical reaction is shown below.

Organic Chemistry, Chapter 21, Problem 21.45P , additional homework tip  8

Figure 4

Conclusion
Interpretation Introduction

(e)

Interpretation:

The product formed on treatment of phenylacetaldehyde with given reagent is to be predicted.

Concept introduction:

In Wittig reaction, aldehyde can be directly converted to alkene using triphenyl phosphonium ylide. The geometry of the alkene formed, depends on the stability of the ylides.

Expert Solution
Check Mark

Answer to Problem 21.45P

The product formed on treatment of phenylacetaldehyde with given reagent is,

Organic Chemistry, Chapter 21, Problem 21.45P , additional homework tip  9

Explanation of Solution

Phenylacetaldehyde on reaction with Wittig reagent Ph3P=CHCH3 yields alkene. The corresponding chemical reaction is shown below.

Organic Chemistry, Chapter 21, Problem 21.45P , additional homework tip  10

Figure 5

The products formed are (E)-but-2-en-1-ylbenzene and (Z)-but-2-en-1-ylbenzene.

Conclusion

The product formed on treatment of phenylacetaldehyde with given reagent is shown in figure 5.

Interpretation Introduction

(f)

Interpretation:

The product formed on treatment of phenylacetaldehyde with given reagent is to be predicted.

Concept introduction:

Aldehyde or ketone on reaction with primary amine forms imine. Imine is also known as Schiff base. The nucleophilic attack of primary amine on carbonyl carbon results in the formation of intermediate carbinolamine. This intermediate loses water to form an imine.

Expert Solution
Check Mark

Answer to Problem 21.45P

The product formed on treatment of phenylacetaldehyde with given reagent is,

Organic Chemistry, Chapter 21, Problem 21.45P , additional homework tip  11

Explanation of Solution

Phenylacetaldehyde reacts with (CH3)2CHNH2 in presence of mild acid to form imine. The corresponding reaction is as follows,

Organic Chemistry, Chapter 21, Problem 21.45P , additional homework tip  12

Figure 6

The product formed is N-(2-phenylethylidene) propan-2-amine.

Conclusion

The product formed on treatment of phenylacetaldehyde with given reagent is shown in figure 6.

Interpretation Introduction

(g)

Interpretation:

The product formed on treatment of phenylacetaldehyde with given reagent is to be predicted.

Concept introduction:

Aldehyde or ketone on reaction with secondary amine forms enamine. The nucleophilic attack of secondary amine on carbonyl carbon results in the formation of intermediate carbinolamine. This intermediate loses water to form an enamine. In this case, the elimination occurs across two adjacent carbon atoms to form new carbon-carbon double bond.

Expert Solution
Check Mark

Answer to Problem 21.45P

The product formed on treatment of phenylacetaldehyde with given reagent is,

Organic Chemistry, Chapter 21, Problem 21.45P , additional homework tip  13

Explanation of Solution

Phenylacetaldehyde reacts with (CH3CH2)2NH in presence of mild acid to form enamine. The corresponding reaction is as follows,

Organic Chemistry, Chapter 21, Problem 21.45P , additional homework tip  14

Figure 7

The products formed are (E)-N,N-diethyl-2-phenylethanamine and (Z)-N,N-diethyl-2-phenylethanamine.

Conclusion

The product formed on treatment of phenylacetaldehyde with given reagent is shown in figure 7.

Interpretation Introduction

(h)

Interpretation:

The product formed on treatment of phenylacetaldehyde with given reagent is to be predicted.

Concept introduction:

Aldehydes or ketones on reaction with one equivalent of alcohol form hemiacetal and on reaction with two equivalents of alcohol it forms acetals. This is nucleophilic addition reaction. These reactions take place in presence of acids.

Expert Solution
Check Mark

Answer to Problem 21.45P

The product formed on treatment of phenylacetaldehyde with given reagent is,

Organic Chemistry, Chapter 21, Problem 21.45P , additional homework tip  15

Explanation of Solution

Phenylacetaldehyde reacts with excess of ethanol in presence of acid to form acetal. The corresponding reaction is as follows,

Organic Chemistry, Chapter 21, Problem 21.45P , additional homework tip  16

Figure 8

The product formed is (2,2-diethoxyethyl) benzene.

Conclusion

The product formed on treatment of phenylacetaldehyde with given reagent is shown in figure 8.

Interpretation Introduction

(i)

Interpretation:

The product formed on treatment of phenylacetaldehyde with given reagent is to be predicted.

Concept introduction:

Aldehyde or ketone on reaction with secondary amine forms enamine. The nucleophilic attack of secondary amine on carbonyl carbon results in the formation of intermediate carbinolamine. This intermediate loses water to form an enamine. In this case the elimination occurs across two adjacent carbon atoms to form new carbon-carbon double bond.

Expert Solution
Check Mark

Answer to Problem 21.45P

The product formed on treatment of phenylacetaldehyde with given reagent is,

Organic Chemistry, Chapter 21, Problem 21.45P , additional homework tip  17

Explanation of Solution

Phenylacetaldehyde reacts with piperidine in presence of mild acid to form E and Z isomers of 1-styrlpiperidine. The corresponding reaction is as follows,

Organic Chemistry, Chapter 21, Problem 21.45P , additional homework tip  18

Figure 9

Conclusion

The product formed on treatment of phenylacetaldehyde with given reagent is shown in figure 9.

Interpretation Introduction

(j)

Interpretation:

The product formed on treatment of phenylacetaldehyde with given reagent is to be predicted.

Concept introduction:

Aldehydes or ketones on reaction with one equivalent of alcohol form hemiacetal and on reaction with two equivalents of alcohol it forms acetals. This is nucleophilic addition reaction. These reactions take place in presence of acids.

Expert Solution
Check Mark

Answer to Problem 21.45P

The product formed on treatment of phenylacetaldehyde with given reagent is,

Organic Chemistry, Chapter 21, Problem 21.45P , additional homework tip  19

Explanation of Solution

Phenylacetaldehyde reacts with ethane-1,2-diol in presence of acid to form cyclic acetal. The corresponding reaction is as follows,

Organic Chemistry, Chapter 21, Problem 21.45P , additional homework tip  20

Figure 10

The product formed is 2-benzyl-1,3-dioxolane.

Conclusion

The product formed on treatment of phenylacetaldehyde with given reagent is shown in figure 10.

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Chapter 21 Solutions

Organic Chemistry

Ch. 21 - Prob. 21.11PCh. 21 - Prob. 21.12PCh. 21 - Prob. 21.13PCh. 21 - Prob. 21.14PCh. 21 - Problem 21.15 Draw the product of each...Ch. 21 - Prob. 21.16PCh. 21 - Prob. 21.17PCh. 21 - Outline a synthesis of each Wittig reagent from...Ch. 21 - Draw the products including stereoisomers formed...Ch. 21 - Prob. 21.20PCh. 21 - Prob. 21.21PCh. 21 - Show two methods to synthesize each alkene: a...Ch. 21 - Problem 21.22 The product formed when reacts with...Ch. 21 - What 1 amine and carbonyl compound are needed to...Ch. 21 - Prob. 21.25PCh. 21 - Prob. 21.26PCh. 21 - Prob. 21.27PCh. 21 - Problem 21.28 Draw a stepwise mechanism for the...Ch. 21 - Problem 21.29 Draw the products of each...Ch. 21 - Problem 21.30 Label each compound as an acetal, a...Ch. 21 - Problem 21.31 Draw a stepwise mechanism for the...Ch. 21 - Problem 21.32 Draw the products of each...Ch. 21 - Problem 21.33 Safrole is a naturally occurring...Ch. 21 - Problem 21.35 How would you use a protecting group...Ch. 21 - Prob. 21.35PCh. 21 - Problem 21.37 Two naturally occurring compounds...Ch. 21 - Problem 21.38 Draw the products of each...Ch. 21 - Prob. 21.38PCh. 21 - Problem 21.40 (a) Give the IUPAC name for A and B....Ch. 21 - 21.41 Rank the following compounds in order of...Ch. 21 - Prob. 21.41PCh. 21 - Give the IUPAC name for each compound. a. d. g. b....Ch. 21 - Give the structure corresponding to each name. a....Ch. 21 - Including stereoisomers, draw the 11 aldehydes...Ch. 21 - Prob. 21.45PCh. 21 - Prob. 21.46PCh. 21 - What alkyl halide is needed to prepare each Wittig...Ch. 21 - 21.46 Draw the products of each reaction. a. e....Ch. 21 - Prob. 21.49PCh. 21 - Prob. 21.50PCh. 21 - Prob. 21.51PCh. 21 - Prob. 21.52PCh. 21 - Prob. 21.53PCh. 21 - Rank the following compounds in order of...Ch. 21 - Which compound forms the higher concentration of...Ch. 21 - Prob. 21.56PCh. 21 - What Wittig reagent and carbonyl compound are...Ch. 21 - Prob. 21.58PCh. 21 - What reagents are needed to convert each compound...Ch. 21 - What reagents are needed to convert each compound...Ch. 21 - Prob. 21.61PCh. 21 - Devise a synthesis of each alkene using a Wittig...Ch. 21 - Devise a synthesis of each compound from...Ch. 21 - Prob. 21.64PCh. 21 - Prob. 21.65PCh. 21 - Prob. 21.66PCh. 21 - Prob. 21.67PCh. 21 - Prob. 21.68PCh. 21 - Prob. 21.69PCh. 21 - 21.64 Draw a stepwise mechanism for the following...Ch. 21 - 21.65 Draw a stepwise mechanism f or the following...Ch. 21 - Prob. 21.72PCh. 21 - 21.67 Draw a stepwise mechanism for each...Ch. 21 - 21.68 Draw a stepwise mechanism for the following...Ch. 21 - Prob. 21.75PCh. 21 - Prob. 21.76PCh. 21 - Prob. 21.77PCh. 21 - Prob. 21.78PCh. 21 - Prob. 21.79PCh. 21 - 21.73 Although the carbonyl absorption of cyclic...Ch. 21 - 21.74 Use the and data to determine the...Ch. 21 - 21.75 A solution of acetone in ethanol in the...Ch. 21 - Compounds A and B have molecular formula ....Ch. 21 - 21.77 An unknown compound C of molecular formula ...Ch. 21 - 21.78 An unknown compound D exhibits a strong...Ch. 21 - Prob. 21.86PCh. 21 - -D-Glucose, a hemiacetal, can be converted to a...Ch. 21 - 21.81 Draw a stepwise mechanism for the following...Ch. 21 - Prob. 21.89PCh. 21 - Prob. 21.90PCh. 21 - Prob. 21.91PCh. 21 - 21.86 Draw stepwise mechanism for the following...
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