{
"cells": [
{
"cell_type": "markdown",
"metadata": {},
"source": [
"$\\require{mhchem}$"
]
},
{
"cell_type": "markdown",
"metadata": {},
"source": [
"\n",
" Amines"
]
},
{
"cell_type": "markdown",
"metadata": {},
"source": [
""
]
},
{
"cell_type": "markdown",
"metadata": {},
"source": [
"#### Quaternary ammonium salts have 4 alkyl or aryl bonds to a nitrogen atom"
]
},
{
"cell_type": "markdown",
"metadata": {},
"source": [
""
]
},
{
"cell_type": "markdown",
"metadata": {},
"source": [
"### Trimethylamine shows less angle compression than ammonia. Why?"
]
},
{
"cell_type": "markdown",
"metadata": {},
"source": [
""
]
},
{
"cell_type": "markdown",
"metadata": {},
"source": [
""
]
},
{
"cell_type": "markdown",
"metadata": {},
"source": [
"#### Amines have large dipole moment. Why?\n",
"#### Amines form weaker hydrogen bonds than do alcohols of similar molecular weights. Why?"
]
},
{
"cell_type": "markdown",
"metadata": {},
"source": [
""
]
},
{
"cell_type": "markdown",
"metadata": {},
"source": [
"### Amines can act as both nucleophile and base. Stronger bases have smaller pKb value"
]
},
{
"cell_type": "markdown",
"metadata": {},
"source": [
""
]
},
{
"cell_type": "markdown",
"metadata": {},
"source": [
""
]
},
{
"cell_type": "markdown",
"metadata": {},
"source": [
"### Amino groups are strong activating groups and ortho, para-directors."
]
},
{
"cell_type": "markdown",
"metadata": {},
"source": [
""
]
},
{
"cell_type": "markdown",
"metadata": {},
"source": [
"### The --NH3+ group is strongly deactivating (and meta-allowing)"
]
},
{
"cell_type": "markdown",
"metadata": {},
"source": [
""
]
},
{
"cell_type": "markdown",
"metadata": {},
"source": [
"### Pyridine resembles a strongly deactivated benene"
]
},
{
"cell_type": "markdown",
"metadata": {},
"source": [
""
]
},
{
"cell_type": "markdown",
"metadata": {},
"source": [
"### Why attack at the 2-position (or 4-position) is not observed?"
]
},
{
"cell_type": "markdown",
"metadata": {},
"source": [
""
]
},
{
"cell_type": "markdown",
"metadata": {},
"source": [
"### Syntheses Limited to Primary Amines"
]
},
{
"cell_type": "markdown",
"metadata": {},
"source": [
""
]
},
{
"cell_type": "markdown",
"metadata": {},
"source": [
"
"
]
},
{
"cell_type": "markdown",
"metadata": {},
"source": [
"
"
]
},
{
"cell_type": "markdown",
"metadata": {},
"source": [
"What is a benzyl group? \n",
"Answer: \n",
"
C6H5CH2-
" ] }, { "cell_type": "markdown", "metadata": {}, "source": [ "Draw the structure of butyric acid with representation of alpha, beta and gamma carbon. \n", "Answer::\n", "The alpha carbon (Cα) in organic molecules refers to the first carbon atom that attaches to a functional group, such as a carbonyl. The second carbon atom is called the beta carbon (Cβ),[1] and the system continues naming in alphabetical order with Greek letters.
" ] }, { "cell_type": "markdown", "metadata": {}, "source": [ " Why N-H bond of phthalimide is a lot more acidic than it normally would be?\n", " Hint: How to know the acidity of a molecule? \n", " Answer: \n", "because the resulting anion will be resonance stabilized.
" ] }, { "cell_type": "markdown", "metadata": {}, "source": [ "Identify and name the nucleophile, electrophile and leaving group in the SN2 reaction of Gabriel Synthesis." ] }, { "cell_type": "markdown", "metadata": {}, "source": [ "Can you say why we can only prepare primary ammines in Gabriel Synthesis?" ] }, { "cell_type": "markdown", "metadata": {}, "source": [ "The conversion of primary aromatic amines into diazonium salts in known as______. \n", "\n", "**Connection**: \n", "Elaborate Sandmeyer's reaction and diazotization reaction." ] }, { "cell_type": "markdown", "metadata": {}, "source": [ "Write the IUPAC name of the given compound?" ] }, { "cell_type": "markdown", "metadata": {}, "source": [ "" ] }, { "cell_type": "markdown", "metadata": {}, "source": [ "**Answer**: \n", "2,4,6-Tribromoaniline
" ] }, { "cell_type": "markdown", "metadata": {}, "source": [ "**Connection**: \n", "What the name of given compound?" ] }, { "cell_type": "markdown", "metadata": {}, "source": [ "" ] }, { "cell_type": "markdown", "metadata": {}, "source": [ "**Answers**: \n", "Aniline
\n" ] }, { "cell_type": "markdown", "metadata": {}, "source": [ "Give the IUPAC name and structure of the amine obtained when 3-chlorobutanamide undergoes Hoffmann-bromamide reaction." ] }, { "cell_type": "markdown", "metadata": {}, "source": [ "**Connection**: \n", "What is an amide? " ] }, { "cell_type": "markdown", "metadata": {}, "source": [ "Draw the structure of 3-chlorobutanamide?" ] }, { "cell_type": "markdown", "metadata": {}, "source": [ "" ] }, { "cell_type": "markdown", "metadata": {}, "source": [ "** Hoffmann-bromamide reaction **" ] }, { "cell_type": "markdown", "metadata": {}, "source": [ "$$ \\ce{RCONH2 +Br2 + 4NaOH -> R-NH2 + Na2CO3 + 2NaBr + 2H2O} $$\n", "\n", "Remember carbonyl group is removed, so there is decrease in C number in $\\ce{R-NH2}$" ] }, { "cell_type": "markdown", "metadata": {}, "source": [ "**Answer**:\n", "3-Chloropropanamine
" ] }, { "cell_type": "markdown", "metadata": {}, "source": [ "Complete the following reaction equation: \n", "$$ \\ce{C6H5N2Cl + H3PO2 + H2O -> } $$\n" ] }, { "cell_type": "markdown", "metadata": {}, "source": [ "What is the name of $\\ce{C6H5N2Cl}$ ? \n", "**Answer**:Benzenediazonium chloride (Diazonium salt)
" ] }, { "cell_type": "markdown", "metadata": {}, "source": [ "### Aryl diazonium salts as intermediates\n", "Aryl diazonium salts are important intermediates. They are prepared in cold (0 º to 10 ºC) aqueous solution, and generally react with nucleophiles with loss of nitrogen. Some of the more commonly used substitution reactions are shown in the following diagram. Since the leaving group ($\\ce{N2}$) is thermodynamically very stable, these reactions are energetically favored. Those substitution reactions that are catalyzed by cuprous salts are known as Sandmeyer reactions. The top reaction with hypophosphorus acid, $\\ce{H3PO2}$, is noteworthy because it achieves the reductive removal of an amino (or nitro) group. Unlike the nucleophilic substitution reactions, this reduction probably proceeds by a radical mechanism." ] }, { "cell_type": "markdown", "metadata": {}, "source": [ "" ] }, { "cell_type": "markdown", "metadata": {}, "source": [ "What is the name of $\\ce{H3PO2}$? State whether its oxidising or reducing agent? \n", "Answer: \n", "Hypophosphorous acid, reducing agent
" ] }, { "cell_type": "markdown", "metadata": {}, "source": [ "" ] }, { "cell_type": "markdown", "metadata": {}, "source": [ "Can you say which carbon of diazonium salt under go reduction when treated with hypophosphorous acid? Explain the complete reduction process using oxidation states of carbon." ] }, { "cell_type": "markdown", "metadata": {}, "source": [ "Question: \n", "Arrange the following in increasing order of basic strength: Aniline, p-Nitroaniline and p-Toluidine" ] }, { "cell_type": "markdown", "metadata": {}, "source": [ "What is the structure of p-Toluidine? Can you recall the structure of Aniline and p-nitoraniline?" ] }, { "cell_type": "markdown", "metadata": {}, "source": [ "Ammoinium ions
" ] }, { "cell_type": "markdown", "metadata": {}, "source": [ "Write down the base dissociation constant along with the reaction." ] }, { "cell_type": "markdown", "metadata": {}, "source": [ "Specify which of the substitute are electron withdrawing and electron donanting in the question." ] }, { "cell_type": "markdown", "metadata": {}, "source": [ "Draw the ammonium ion of each structure given, and arrange according to their stability giving reasons." ] }, { "cell_type": "markdown", "metadata": {}, "source": [ "Question: Arrange the following in the increasing order of their basic strength in aqueous solutions:\n", "CH3NH2, (CH3)2NH, (CH3)3N and NH3" ] }, { "cell_type": "markdown", "metadata": {}, "source": [ "Answer:\n", "\n", "An isocyanide (also called isonitrile or carbylamine) is an organic compound with the functional group -N≡C. It is the isomer of the related cyanide (-C≡N), hence the prefix iso
" ] }, { "cell_type": "markdown", "metadata": {}, "source": [ "The reaction with aniline:" ] }, { "cell_type": "markdown", "metadata": {}, "source": [ "