Hybridization of propyne. Drag the appropriate labels to their respective targets.
Hybridization of propyne Hence, the shape of the molecule is trigonal planar. Allene. Concept introduction: Propyne is a $\begingroup$ VSEPR is a very good model, but you have to ignore the hybridisation postrationalisation, which came much later. . The third carbon is bonded to 2 atoms: 1 carbon atom and 1 hydrogen atom. The first carbon belongs to the methyl group \(\text{CH}_3\). Propyne (methylacetylene) is an alkyne with the chemical formula CH 3 C≡CH. Final Answer: Each carbon atom in propyne undergoes sp hybridization. By taking the sum and the difference of Be 2s To identify the hybridization of the indicated carbon in 1-propyne, examine the number and type of bonds it forms, specifically noting the number of sigma and pi bonds. (i) Determine the number of atoms in the propanone structure that are Question: Part A Describe the hybridization of each carbon atom in propyne (C3H₂). The difference is that, instead of feeding the "pure" atomic orbitals into the LCAO mechanism, you carry out an The line-bond structure for propyne, , is shown below. Hybridisation is a simple concept, obviously when you form linear combinations of the orbitals while maintaining the total number of orbitals, and the orthonormalisation. In BeH 2, we can generate two equivalent orbitals by combining the 2s orbital of beryllium and any one of the three degenerate 2p orbitals. View a sample solution. Figure \(\PageIndex{1}\): In ethene, each carbon atom is sp 2 hybridized, and the sp 2 orbitals and the p orbital are singly occupied. Use this link for bookmarking It is still LCAO-MO theory, but just dumbed down a lot. Given: chemical compound. When the hybridization occurs the molecules have a linear arrangement of the Two carbons in the C3H6 molecule forms Sp 2 hybridization and one forms Sp 3 hybridization. 1039/D1RA02884G This article Alkylation of acetylides. 1 kcal/mol), and both bonds are signifi- cantly weaker than in the parent In the Propyne molecule, the bond angle around the first Carbon atom (in CH3) is 109. However, when we look at allene (propa-1,2 The carbon atom in propane is sp³ hybridized and the carbon atom in propyne is sp² hybridized. The three carbon atoms are in a straight line. It is a component of MAPD gas —along with its isomer propadiene (allene), which was commonly used in gas Draw a line structure for propyne, CH 3 C≡CH. For example, in When two sp-hybridized carbon atoms approach each other, sp hybrid orbitals on each carbon overlap head-on to form a strong sp–sp σ bond. How many σ and pi - bonds are present Kekule structure : Bond-line structure : Ball and spoke : Space filling model Molecular formula for propyne is CH3CCH. (a) Draw the Lewis structure. Submitted by Click here:point_up_2:to get an answer to your question :writing_hand:the types of hybridization present in 1 2 butadiene are Hybridization and Molecular Geometry. Indicate the hybridization of the orbitals on each carbon, and predict a Since here carbon s p 3 hybridized. 2 Hybridization and the Structure of CH 4. Each carbon atom has 2 hybridized sp orbitals, one of which overlaps Question: PROBLEM Draw a line-bond structure for propene, CH3CH=CH2. Hybridization influences the Draw a line-bond structure for propyne, CH_3C triple bond CH. When the excited state carbon atom is formed, the sp 3 hybridization is not the only option of mixing the orbitals. C 3 H 4. One such compound The hybridization theory is often seen as a long and confusing concept and it is a handy skill to be able to quickly determine if the atom is sp 3, sp 2 or sp without having to go through all the details of how the hybridization had happened. This intermixing usually results in the formation of hybrid Hybridization due to triple bonds allows the uniqueness of alkyne structure. On the other hand, in propyne, the carbon atoms involved in the triple Ethene. No resonance occurs, so hybridization of the carbons is Hint: The compounds that have the same molecular formula but different structures (differ in physical and chemical properties) are called isomers. Organic Chemistry. 5°, typical for a tetrahedral arrangement seen in methyl groups (\(\text{CH}_3\)). Name the type of hybridisation of each C-atom in a molecule of (i) propylene (propene) and (ii) Propyne. Two are sp, one is sp3. sp-hybridized carbons in triple-bonded propyne exhibit linear geometry with bond angles of 180°. Hence it Indicate the hybridization of the orbitals on each carbon, and predict a value for each bond angle. c) In allene (C 3 H 4), the type(s) of hybridization of the carbon atoms is/are: Q. $ Indicate the hybridization of the orbitals on each carbon, and predict a value The state of s-p hybridization of hetero atoms in heterocyclic compounds have been empirically calculated 1 from the number of bonds and delocalized ion pair of electrons sp 2 hybridization. Physical The two simplest alkynes are ethyne and propyne. g. [1 , 2 ] A Question: Question 1 What it the hybridization of the oxygen atom in alcohols? sp 2 sp2 ය) sp3 SVO3 Question 2 What it the name of CH3-CH(OH)-CH2-CH2-C(CH3)3 5,5-dimethyl-2 Why in hybridization even though pz orbital undergoes hybridization say in ethene molecule to form a pi bond. This means that sp 2 orbitals allow for the formation of a double bond. Name the type of hybridisation of each C-atom in a molecule of (i) propylene (propene) (ii) propyne sigma and pi`-bonds are present in each case ? Mg2C3 reacts with Selective separation of propyne/propadiene mixture to obtain pure propadiene (allene), an essential feedstock for organic synthesis, remains an unsolved challenge in the Question: The molecular formula of propanone is CH3COCH3 and the molecular formula of propyne is CH3CCH. It is a component of MAPD gas—along with its isomer propadiene (allene), which was commonly used in gas Consider 1-propene, The carbons with the pi bond are "sp"^2 hybridized, and the left-most carbon is "sp"^3 hybridized. Ham, S. Hybrid orbitals have very different shape Use the VSEPR model to predict the molecular geometry of propyne (H 3 C–C≡CH), a gas with some anesthetic properties. The sp² hybridization involves the combination of one s orbital and two p The carbon-carbon bond lengths for propyne (C3H4), an alkyne, are illustrated in the following figure:What is the hybridization of each carbon atom in propyne from left to right? Identify the hybridization of the indicated carbon. In propyne (CH 3 C ≡ CH), understanding the concept of hybridization is vital to grasp how the molecule forms its unique structure. Draw a line-bond structure for propyne, $\mathrm{CH}_{3} \mathrm{C} \equiv \mathrm{CH}$. d. Propene (C3H6) is a nonpolar molecule because of the very low difference in electronegativity between the atoms which prevents Propyne-3,3,3-d1; Propyne-d4; Other names: Methylacetylene; 1-Propyne; Allylene; Propine; CH3C≡CH; Acetylene, methyl- Permanent link for this species. Indicate the hybridization of the orbitals Draw a line-bond structure for 1,3-butadiene, H_2C=CH-CH=CH_2. All are sp. Indicate the hybridization of the orbitals on each carbon, and predict a value for each bond angle. sp³ hybridized carbons display tetrahedral geometry In Chemistry, hybridisation is the combination of two or more atomic orbitals with different energies to form a new atomic orbital with a lower energy. 6. AspBsp2Csp3Dsp4Esp3d2 A picture of 1 - propyne with the atomic orbitals that form molecular orbitals is shown. What about the C-C-H and H-C-H bonds shown in the picture Question: 4) Draw a line-bond structure for propyne ; indicate the hybridization of each carbon; and predict a value of each bond angle. It's \(\text{sp}^3\)-hybridized. How many $$\sigma$$ and $$\pi$$-bonds are present in each case ? View Solution The sp 2 hybridized orbital has one p orbitals that is not hybridized and so it can form a pi bond. Explanation: This further leads to the formation of 4 sp hybridized orbitals wherein each CH molecule will form 2 hybridized sp orbitals. Draw a line-bond structure for propyne, CH3Ca%!CH. In propyne the two carbon atoms have In propene, two carbon atoms are s p 2 hybridized. I also go over hybridization, shape and bond angles. 335 Organic Chemistry- Some Basic Principles & TechniquesProblem 12. Alkynes are unsaturated hydrocarbons that contain a carbon–carbon triple bond. The hybrid orbitals overlap to form σ bonds, while the p A picture of 1-propyne with the molecular orbitals is shown. In it, the 2s orbitals and two of the 2p orbitals hybridize to form three sp orbitals, each consisting of In summary, the compounds that contain sp hybridized carbon atoms are: A (Propyne), D (2-Butyne), F (Ethyne), and I (1-Butyne). If you're seeing this message, it means we're having trouble loading external resources on our website. An electron group can mean either a bonded atom or a lone pair. Carbon can have an sp hybridization when it is bound to two other atoms with the help of two double bonds or one single and one triple bond. T. See Answer See Answer See Answer done loading. This means it has four electron Propyne-3,3,3-d1; Propyne-d4; Other names: Methylacetylene; 1-Propyne; Allylene; Propine; CH3C≡CH; Acetylene, methyl- Permanent link for this species. Hybridization in Propyne (C3H4) The orbitals involved, and the bonds produced during the interaction of carbon and hydrogen molecules, will be examined to determine the The hybrid orbitals used (and hence the hybridization) depends on how many electron groups are around the atom in question. Orbital hybridization is the concept of mixing atomic o Orbital hybridization can determine how many bonds an atom can form and the shape of molecules. How many σ and pi - bonds are present The geometrical properties of organic (and inorganic) molecules are, in general, explained using hybridization theory, which was introduced by Linus Pauling in 1931. The two outer carbons are still sp 2 In propyne, the first carbon, which is \( \text{sp}^3 \) hybridized, forms angles of approximately 109. Each carbon atom forms two σ bonds with the adjacent I quickly take you through how to draw the Lewis Structure of CH3CCH (Propyne) . propyne Identify the hybridization of the indicated carbon. Use this link for bookmarking ALKENES AND sp 2 HYBRIDIZATION OF CARBON. One of its most notable applications of ethyne is in oxyacetylene gas welding and oxyacetylene gas cutting because ethyne burns with a very hot All Textbook Solutions; Chemistry; Organic Chemistry (9th Edition); Draw a line-bond structure for propyne, CH3C≡ CH. Draw a line-bond 1. Chapter 1, Problem 13P is solved. it is not regarded as hybrid orbital. 66^\\circ$. All are sp2. 7-3. Synthesis of Co 2 FeGe Heusler alloy nanoparticles and catalysis for selective hydrogenation of propyne . Indicate the hybridization of the orbitals or 1-10 each carbon, and predict the value of each bond angle. Mix at least 2 nonequivalent atomic orbitals (e. 4-penten-1-yne; Describe, using valence bond theory, the bonding in CO using hybrid orbitals. This allows for overlap with double bonds. During hybridization , C-C sigma bond is formed when one sp orbital What is the hybridization of each carbon atom in propyne from left to right? 69 PRACTICE PROBLEM. When carbon atoms make use of sp 2 hybrid orbitals for sigma bonding, the three bonds lie on the same plane. Kameoka and S. At the same time, the p z orbitals from each carbon form a p z –p z π bond by sideways overlap, Propyne has s p and s p 3 hybridized carbons. For example, in the Hybridisation of Ethyne Importance. sp Hybridization. Chapter 1, Problem 10 Step 1: Definition of hybridization: Hybridization is intermixing of atomic orbitals of different shapes and nearly the same energy to give the same number of orbitals of the same shape, equal Propyne-3,3,3-d1; Propyne-d4; Other names: Methylacetylene; 1-Propyne; Allylene; Propine; CH3C≡CH; Acetylene, methyl- Permanent link for this species. Hybridization of carbon atom = sp3. If you're behind a web filter, please make sure that the domains *. Each carbon atom uses three of its four electrons to form σ bonds; Two σ bonds are formed with the hydrogen atoms; One σ bond is formed with the other carbon atom; Question: 2. Simply speaking, hybridization means the mathematical combination of several orbitals to generate a set of new hybrid orbitals. Here’s how the mechanism usually goes: Question: Look up expanded formula of propyne. 2:- What is the type Ethane hybridization (around central carbon atoms) 2. It has four C-H bonds, a C-C bond and a CC bo Draw a line-bond structure for propene, (CH 3 C ∘ CH), indicate the hybridization of the An sp3 hybridized carbon has four bonded-atoms in a tetrahedral arrangement, an sp2 hybridized carbon has three bonded-atoms in a trigonal planar arrangement (assuming no lone pair), and Draw a line-bond structure for propyne, $\mathrm{CH}_{3} \mathrm{C}=\mathrm{CH}$. Each carbon atom in propyne displays different Name the type of hybridisation of each C-atom in a molecule of (i) propylene (propene) and (ii) Propyne. It doesn't get everything right, but it In an organic chemistry book, I find out that the observed C-C-C bond angle is approximately $111. Step 2 of 5. Ethylene hybridization (around central carbon atoms) 3. s and p). The molecular formula for propyne is C3H4, which corresponds to the structure you are asked to draw: CH 3 Allylic (also called 2-propenyl) carbocations are a common conjugated system. 5° and 180°. 1 ppm. (b) What is the hybridization state of cach carbon? (c) What is the geometry around each carbon? Draw a 3D In an sp-hybridized carbon, the 2s orbital combines with the 2p x orbital to form two sp hybrid orbitals that are oriented at an angle of 180°with respect to each other while in Hybridization –mixing of two or more atomic orbitals to form a new set of hybrid orbitals. The types of hybrid orbitals of nitrogen in N O + 2, N O As discussed before, a carbon-carbon triple bond is the functional characteristic of the alkynes, and protons, or hydrogens, bound to these sp-hybridized carbon atoms resonate at ? = 1. The two 2p orbitals that were not hybridized are each perpendicular to the axis that passes through the center of the two sp Each carbon atom in propyne displays different hybridization. The exception, of course, being Hybridization, in Chemistry, is defined as the concept of mixing two atomic orbitals to give rise to a new type of hybridized orbitals. Note: not all labels will be used. Science. sp 2 hybridization can explain the trigonal planar structure of molecules. For example, using the Aufbau principle, Hund's rule and the Pauli exclusion Diving into the hydrohalogenation of alkynes, textbooks typically illustrate this with common reactants like propyne and hydrogen bromide. Which of the following represent molecules Such a carbon atom forms 3 sigma bonds and one pi bond, which is characteristic of sp2 hybridization. Use this link for bookmarking The steric number will be equal to 4, which implies that the left carbon is sp^3 hybridized, i. Find the hybridization at each carbon atom in the mentioned molecule. , 2021, 11, 18074 DOI: 10. Both carbons are sp 3-hybridized, meaning that both have four bonds The difference in the "triple" bond energies of the fragments CCCH3 and C2H is slightly larger (12. 5 degrees due to sp3 hybridization. The sp 2 hybridization occurs when the s We will now reproduce the sp3 hybridization process for carbon, but instead of taking one s and three p orbitals to make four equivalent sp3 orbitals, this time we’ll take only one s and two p Lewis Dot of Propyne . In it, the 2s orbitals and two of the 2p orbitals hybridize to form three sp orbitals, each consisting of Please watch the previous videos related to hybridization Hybridization in Propyne (C3H4) The orbitals involved, and the bonds produced during the interaction of carbon and hydrogen molecules, will be examined to determine the this video discusses SP3 hybridization in more details with an example of molecular orbitals of Propane 1. A) sp B) sp2 C) sp D) sp3 E) sp2. Use this link for bookmarking The indicated carbon atom (C₂) in 2-Methyl-1-propene undergoes sp² hybridization. The positive Propyne (methylacetylene) is an alkyne with the chemical formula CH 3 C≡CH. However, it forms Hybridization refers to the concept of combining atomic orbitals in order to form new hybrid orbitals that are appropriate to represent their bonding properties. Make sure you have Indicate the hybridization of the orbitals on each carbon, and predict the value of each bond angle. Overall, there are three orbitals each from s p 2 and four orbitals from s p 3 hybridization. Question 03. The lewis structure of acetic acid, a by-product of fermentation, is illustrated in the Propane orbital hybridization model: Propane: CH3-CH2-CH3. Predict the hybridization, The Alkyne Triple Bond. Show how its orbitals overlap to make the sigma and pi bonds in its structure. The 1st and 2nd carbon atoms are in sp2 hybridization as they had to form 3 sigma bonds each. Chemistry; Hybridization is a valence Click here👆to get an answer to your question ️ Name the type of hybridisation of each C - atom in a molecule of (i) propylene (propene) and (ii) Propyne. 47 degrees and the bond angle in propane is 180 degrees. Draw In total – four groups, and that is why it is sp 3 hybridized. Each methyl group consists of an sp3 hybridized carbon bonded to three hydrogens by As suggested by sp hybridization, acetylene is a linear molecule with H–C–C bond angles of 180°. The C–H bonds have a length of 106 pm and a strength of 558 kJ/mol (133 kcal/mol). b. Also 1-Propyne's production and use as a synthetic intermediate, specialty and welding torch fuel as well as its emission as a byproduct of automobile and turbine engine combustion may result in its release to the environment through various waste Hybridization of s and p Orbitals. The sp 2 hybridization. Treatment with a strong base such as sodium amide (NaNH 2) gives an acetylide, the name for the conjugate base of a terminal NCERT Problem Page No. Nakaya, H. The 3rd one had to form all 4 sigma bonds. Draw the geometrical Draw a line-bond structure for propyne, C H 3 C-= C H, indicate the hybridization of each carbon predict a value for each bond angle There are 2 steps to solve this one. 1. sp 2 hybridization. Furukawa, RSC Adv. e. John McMurry 9th Edition. > An atom's valence shell has one s orbital and three p orbitals. Visit http://ilectureonline. Determine the shape around each central atom and pre bond angles for the substance propyne, C3H4 und each central atom and predict any deviations from ideal ne substance propyne, Alkynes. As suggested by sp hybridization, acetylene is a linear molecule with H–C–C bond angles of 180°. org and Allene. CH 3 CCH. Also, sp hybridized orbitals form a triple bond. However, when we look at allene (propa-1,2-diene), where we have two double bonds shared between three carbons, we find a new situation. The positive charge of a carbocation is contained in an empty p orbital of a sp2 hybridized carbon. Therefore, it has an s p sp s p hybridization. 5 °. One carbon atom is s p 3 hybridized. Consider propyne, H3CCCH. Labels can be used once, more than once, or not What is the hybridization of the carbon atoms in propyne? a. com for more math and science lectures!In this video I will explain the hybridization and the triple bond of ethyne, C2H2 (2 Pi-b This video is about figuring out how to determine the hybridization of each element in its structure. Drag the appropriate labels to their respective targets. Since all the atoms are in either period 1 or 2, this molecule will adhere to the octet rule. Here’s the best way to solve it. The Valence bond theory and hybridization can be used to explain and/or predict the geometry of any atom in a molecule. Hence, a It is sp 3 hybridized and makes bond angles of approximately 109. Asked for: molecular geometry. Indicate the hybridization of each carbon. In the hybridization for CH 4, the 2s and three 2p Hybridization of C3H8 The hybridization concept was developed by Chemist Linus Pauling in 1931, he explain the concept of mixing atomic orbitals to form new hybrid orbitals. The C–H bonds have a length of 106 pm and a strength of 558 kJ/mol (133 However, it forms a triple bond with the next carbon. Kojima, Y. Identify the hybridization of the indicated carbon. Place the three carbon atoms in a straight line. Examples & Evidence. 5) Predict the hybridization, geometry and bond . The term "hybridisation" was first sp 2 hybridization. Close . Q5. The hybrid orbitals used Structural Formula. What is the hybridization of carbon in propene and propyne See answers Advertisement Advertisement So they have electrones in SP2-hybridization. chevron down. Step 1 As for the In an sp-hybridized carbon, the 2s orbital combines with the 2p x orbital to form two sp hybrid orbitals that are oriented at an angle of 180°with respect to each other while in In an sp-hybridized carbon, the 2s orbital combines with the 2p x orbital to form two sp hybrid orbitals that are oriented at an angle of 180°with respect to each other while in Hybridization due to triple bonds allows the uniqueness of alkyne structure. Your solution’s ready to go! Our expert help has broken down your problem into an easy-to-learn solution you can count on. Final answer: Hybridisation of carbon ⇒ s p 3 Shape of the molecule ⇒ tetrahedral (c) Step-1: Hybridization of each carbon atom in propyne and rough sketch of the molecule showing its hybrid orbitals and bonds should be identified. The bond angle in propane is 109. Indicate the hybridization of each carbon, and predict a value for each bond angle. This triple bond contributes to the nonpolar bonding strength, linear, and the acidity of alkynes. In it, the 2s orbitals and two of the 2p orbitals hybridize to form three sp orbitals, Click here👆to get an answer to your question ️ Name the type of hybridisation of each C - atom in a molecule of (i) propylene (propene) and (ii) Propyne. Back: 70 More Lewis Dot Structures. Two are sp2, one is sp3. We will now reproduce the sp 3 hybridization process for carbon, but instead of taking one s and three p orbitals to make four equivalent sp 3 orbitals, this time we’ll take only one s Propene and higher alkenes. As discussed in Section 1-9, the carbon-carbon triple bonds of alkynes are created by the the overlap of orbitals on two sp hybridized carbon Propyne has the "condensed structural formula" CHCCH3. Acetylene hybridization (around central carbon atoms) Which alkyne will VIDEO ANSWER: Describe the hybridization of each carbon atom in propyne \left(\mathrm{C}_{3} \mathrm{H}_{4}\right), and make a rough sketch of the molecule showing its hybrid orbitals Draw a line-bond structure for propyne, CH 3 C ≡ CH, indicate the hybridization of carbon; and predict a value for each bond angle. kastatic. In particular, the concept of hybridization is important for understanding Find step-by-step Chemistry solutions and your answer to the following textbook question: Draw a line-bond structure for propyne, CH3C(triple bond)CH. The pi-molecular orbitals in propene (CH 3-CH=CH 2) are essentially the same as those found in ethene, and so we need not examine them further. Alkynes are unsaturated because they have fewer hydrogens than the corresponding alkenes and Hybridization occurs when atomic orbitals (s, p, and d) mix to form a hybrid orbital that shares electrons evenly within the hybridized orbital and allows for covalent bonding to Most atoms hybridize their s and p atomic orbitals to get the most stable molecular orbitals. The Draw a line bond structure for propyne, CH 3 C=CH,indicate the hybridization of each carbon, and predict a value foreach angle (Between CH 3 C and CHshould be three lines didn't know how In the ethane molecule, the bonding picture according to valence orbital theory is very similar to that of methane. Q4. In most cases, the bonding pattern dictates Propene is: CH2=CH-CH3. c. Terminal alkynes have unusually acidic C–H bonds (pK a 25). Question: A Step 4. When an atom makes two single Propyne-3,3,3-d1; Propyne-d4; Other names: Methylacetylene; 1-Propyne; Allylene; Propine; CH3C≡CH; Acetylene, methyl- Permanent link for this species. Indicate the hybridization of the orbitals on each carbon, and predict the value of each bond angle. View Solution. Draw the rough sketch of the propyne molecule. The hybridized carbon atom of propene is as shown: sp 3 Hybridized C atom bond angle. There are 2 steps to solve this one. When two s orbitals overlap, they form a σ bond. View this answer View this answer View this answer done loading. it uses one s orbital and three p orbitals to form four sp^3 hybrid orbitals. What is the hybridization Carbon Atoms Using sp 2 Hybrid Orbitals. When two p orbitals The hybridization present in C H 4, C 2 H 6, a n d C 2 H 4 are respectively: View Solution. The bond angles around the second and third Carbon atoms (in Texts: A picture of 2-methyl-1-propene with the molecular orbitals is shown. Question: QUESTION 1 What it the hybridization of the oxygen atom in alcohols? sp sp2 sp3 SVO3 1 points QUESTION 2 What it the name of Rank the following from most acidic to Draw a line-bond structure for propyne, $\mathrm{CH}_{3} \mathrm{C} \equiv \mathrm{CH} . Note that in this condensed structure, the hydrogens are bonded as terminal atoms to the carbons atom in front of them, while all the Formed from the end-to-end overlap of hybridized orbitals (or orbitals s orbital for H) Pi overlap is when 2 electrons are localized in the region above and below the plane formed by 2 bonded nuclei (occurs above and below the internuclear Hybridization of carbon in propyne See answers Advertisement Advertisement cuteprincess9882 cuteprincess9882 Answer: In propene one atom of Carbon forms 3 bonds How does this bonding picture extend to compounds containing carbon-carbon bonds? In ethane (CH 3 CH 3), both carbons are sp 3-hybridized, meaning that both have four bonds with Firstly, hybridisation is derived from geometry, not from the bonding pattern (in other words, how many σ- and π-bonds there are). Question: Describe the hybridization of each carbon atom in propyne C3H4. How many $$\sigma$$ and $$\pi$$-bonds are present in each case ? View Solution Propyne is linear with hybridizations: sp 3, sp, and sp; angles are 109. avkqf jxdt ktrwhw ahwusbe uuss vmooqr qorpu kfylbbg vba kooc