Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Question
Chapter 24.6, Problem 11P
Interpretation Introduction
a)
Interpretation:
To describe how the
Interpretation Introduction
b)
Interpretation:
To describe how the amines to be prepared using reductive amination reactions
Interpretation Introduction
c)
Interpretation:
To describe how the amines to be prepared using reductive amination reactions.
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Show how to synthesize the following amines from the indicated starting materials below. Each of the final products may require several sequential steps. Draw the structure for each of the steps and show the reagents required.
Starting material
Final product
b)
Benzene
m-bromoaniline
c)
ethylbenzene
p-ethylaniline + o-ethylaniline
d)
benzene
p-bromoaniline + o-bromoaniline
Show how to prepare the following aromatic amines by aromatic nitration, followed by reduction. You may use benzene andtoluene as your aromatic starting materials. p-bromoaniline
a) What are the difficulties with the following reaction to synthesize an amine.
+ HBr
Br + NH3
NH2
b) Show a possible alternatives to this synthesis.
Chapter 24 Solutions
Organic Chemistry
Ch. 24.1 - Name the following compounds:Ch. 24.1 - Prob. 2PCh. 24.1 - Prob. 3PCh. 24.3 - Prob. 4PCh. 24.3 - The benzylammonium ion (C6H5CH2NH3+) has pKa =...Ch. 24.4 - Prob. 6PCh. 24.5 - Prob. 7PCh. 24.6 - Prob. 8PCh. 24.6 - Prob. 9PCh. 24.6 - Show two methods for the synthesis of dopamine, a...
Ch. 24.6 - Prob. 11PCh. 24.6 - Prob. 12PCh. 24.6 - Prob. 13PCh. 24.7 - Prob. 14PCh. 24.7 - Prob. 15PCh. 24.8 - Prob. 16PCh. 24.8 - Propose syntheses of the following compounds from...Ch. 24.8 - How would you prepare the following compounds from...Ch. 24.8 - Prob. 19PCh. 24.9 - Draw an orbital picture of thiazole. Assume that...Ch. 24.9 - Prob. 21PCh. 24.9 - Prob. 22PCh. 24.9 - Which nitrogen atom in the hallucinogenic indole...Ch. 24.9 - Prob. 24PCh. 24.10 - Prob. 25PCh. 24.SE - Name the following amines, and identify each as...Ch. 24.SE - The following compound contains three nitrogen...Ch. 24.SE - Name the following amine, including R, S...Ch. 24.SE - Prob. 29VCCh. 24.SE - Predict the product(s) for each reaction below and...Ch. 24.SE - Predict the product(s) and provide the complete...Ch. 24.SE - Prob. 32MPCh. 24.SE - Predict the product(s) and provide the mechanism...Ch. 24.SE - The diazotization of aniline first involves the...Ch. 24.SE - Prob. 35MPCh. 24.SE - Prob. 36MPCh. 24.SE - Prob. 37MPCh. 24.SE - Prob. 38MPCh. 24.SE - Choline, a component of the phospholipids in cell...Ch. 24.SE - Prob. 40MPCh. 24.SE - -Amino acids can be prepared by the Strecker...Ch. 24.SE - Prob. 42MPCh. 24.SE - Prob. 43MPCh. 24.SE - Prob. 44MPCh. 24.SE - Propose a mechanism for the following reaction:Ch. 24.SE - Prob. 46MPCh. 24.SE - Name the following compounds:Ch. 24.SE - Prob. 48APCh. 24.SE - Prob. 49APCh. 24.SE - Prob. 50APCh. 24.SE - Histamine, whose release in the body triggers...Ch. 24.SE - Prob. 52APCh. 24.SE - Prob. 53APCh. 24.SE - Prob. 54APCh. 24.SE - Prob. 55APCh. 24.SE - Prob. 56APCh. 24.SE - Prob. 57APCh. 24.SE - Prob. 58APCh. 24.SE - Prob. 59APCh. 24.SE - Prob. 60APCh. 24.SE - Show the products from reaction of p-bromoaniline...Ch. 24.SE - Prob. 62APCh. 24.SE - How would you prepare the following compounds from...Ch. 24.SE - Prob. 64APCh. 24.SE - Phenacetin, a substance formerly used in...Ch. 24.SE - Prob. 66APCh. 24.SE - Draw the structure of the amine that produced the...Ch. 24.SE - Fill in the missing reagents a-e in the following...Ch. 24.SE - Prob. 69APCh. 24.SE - Prob. 70APCh. 24.SE - Deduce the structure of the compound with formula...Ch. 24.SE - Prob. 72APCh. 24.SE - Prob. 73APCh. 24.SE - Prob. 74APCh. 24.SE - Prob. 75APCh. 24.SE - Prob. 76APCh. 24.SE - Propose a structure for the product with formula...Ch. 24.SE - Prob. 78APCh. 24.SE - Prob. 79APCh. 24.SE - Prob. 80APCh. 24.SE - Prob. 81APCh. 24.SE - Prob. 82APCh. 24.SE - Prob. 83APCh. 24.SE - Prob. 84AP
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- Show how to synthesize the following amines from the indicated starting materials below. Each of the final products may require several sequential steps. Draw the structure for each of the steps and show the reagents required. Starting material Final product h) 4-ethyl-3-methylhexan-1-ol 4-ethyl-3-methylhexan-1-amine i) 2-phenylacetyl chloride N-N-dimethyl-2-phenylethan-1-amine j) ethyl acetate N-ethylpropan-2-aminearrow_forward2262 Sat Aor 6 1 Which one of the following compounds is the strongest acid? CNH2 -NH2 -CO2H OH CI- СОН CH CH C A B 2. Which one of the following amines will not produce an amide when mixed with an acid chloride? NH PHCH,NH2 PHNH2 Et,NH A C 3. What is the major product of the following sequence of reactions? CH3 1) NBS, hv (excess) C(OH)3 CHO CO2H CH2O 2) NaOH, H20 (excess) A В C 4. What is the major product of the following intramolecular aldol condensation reaction? E NaOH H20 (dehydration) A C 3. D. Barrow_forward1. Rank the following amines A-D in order of decreasing basicity, where 1 is the most basic. NO2 A B :ZIarrow_forward
- Kindly draw each product for each reaction.arrow_forwardPropose a synthesis for this amine using only primary amines, aldehydes, ketones, carboxylic acid derivatives, or alkyl halides as starting materials. Show all starting materials, reagents, and conditions. oroarrow_forwardShow how to synthesize the following amines from the indicated starting materials byreductive amination. cyclohexylamine from cyclohexanonearrow_forward
- b) Fill in the boxes to synthesize the following primary amines i) ii) iv) Br ΝΗ 1) 2) 3) aqueous workup 1) KOH 2) 3) H2N-NH2 NH3, HOAc, NaCNBH3 1) NaN3 2) PPh 3, H₂O NH₂ NH₂arrow_forwardArrange the following amines in order of increasing basicity. For example, an answer of 1234 would indicate that you think 1 is least basic and 4 is most basicarrow_forwardIndicate whether the following statement is true or false. Aliphatic amines are more basic than ammonia, whereas aromatic amines are less basic than ammonia. When amines are reacted with bases, they form ammonium salts. Benzenesulfonyl chloride or p-toluenesulfonylchloride give N-substituted sulfonamides with primary and secondary amines. Derivative of primary amines is insoluble in dilute NaOHarrow_forward
- Which of the following statements is correct? An aldehyde can react with a secondary amine through a nucleophilic addition-elimination mechanism to give an enamine product. A ketone can react with a secondary amine through a nucleophilic addition mechanism to give an imine product. An ketone can react with a primary amine through a nucleophilic addition-elimination mechanism to give an enamine product. An aldehyde can react with a primary amine through a nucleophilic addition mechanism to give an imine product.arrow_forwardDraw the reactions for the following products (any or all) (include all products).arrow_forwardShow how to synthesize the following amines from the indicated starting materials byacylation–reduction. b) N-benzylaniline from anilinearrow_forward
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